Embracing New Beginnings After Loss: On Dating And Marrying A Widow With Fred Jackson And Lionel Grimes

WRT 30 | Dating A Widow


Dating can be a beautiful beginning from a past relationship. But how do you move forward when you are dating a widow? How do you navigate through their past and help them start anew? In this episode, we dive into the poignant world of dating widows with two guests, Fred Jackson and Lionel Grimes. They open up about their journeys of love and companionship with widows, navigating through its joys and complexities. Fred and Lionel share the beautiful stories of how they met their future wives, the deep connection that blossomed, and the unique challenges of dating individuals who have lost their spouses. They talk about emotional triggers and memories tied to the past and how they approached these moments with unwavering support and empathy. With candid advice for potential partners, Fred and Lionel dive into fostering understanding, patience, and authenticity in relationships. As the conversation draws to a close, Lionel and Fred reflect on their experiences, offering inspiration to those embarking on a similar path and underscoring the remarkable potential for love and meaningful connection when dating widows. We have all loved and lost, and we can also be that new love that can spring in the face of someone’s darkness. Tune in to discover the power of acceptance, communication, and support in the realm of dating after loss.


Thank you for viewing this post. I am not a licensed therapist or professional life coach.

I am sharing my experience of loving the same man for 32 years, a mother to two adult children, a retired military officer, a breast cancer survivor, and my connections with others. 

Anyone experiencing suicidal thoughts should reach out to a suicide hotline or local emergency number in their country: https://www.psychologytoday.com/us/basics/suicide/suicide-prevention-hotlines-resources-worldwide

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Embracing New Beginnings After Loss: On Dating And Marrying A Widow With Fred Jackson And Lionel Grimes

It has been some time since we’ve had an onsite conversation. We are having our episode with Lionel Grimes who is the godfather of my children and my husband, Fred Jackson. I have gotten remarried and I wanted to bring Fred into this conversation. We’re going to have a discussion about dating a widow. Both of these gentlemen are lowkey. That’s why I wanted to interview them together. They’re some smooth fellows. You’ll hear some things that are encouraging to you if you are a widow thinking about dating, you are a gentleman thinking about dating a widow, or maybe a wife thinking about dating a widow. It is possible to love again. It is possible for someone to accept you right where you’re at in this journey of life. Let’s get into this conversation.


WRT 30 | Dating A Widow


Lionel Grimes and Fred Jackson, welcome to the show.

Thank you. Thanks for having me.

Lionel Grimes and Fred Jackson are important to me because Lionel is my children’s godparents and Fred is my husband. I know you are like, “We didn’t talk about that yet,” so here we go. The conversation is about dating widows, and both of these gentlemen have experience with that. I’ll let you talk about your wife. Who is she?

My wife is Kim Grimes. She was formally Kim Clayton then Kim Trewick because she was married before me. She had lost her husband in a military accident, so I’m her second husband. Kim is from Philadelphia. She moved here with her sister. We met at a military conference. It wasn’t one of those things where it was love at first sight. We met and there was a little time in between. If you want to get into that later, we can, but we’ll do that.

Fred, tell us about your initial meeting with your wife.

We met online and set up a date at my favorite coffee shop, Cafe Stella. I had her meet me there one Tuesday after she got off work. We had coffee and talked and went from there.

Was it love at first sight for you?

It was fondness at first sight. When she walked in, she was impressive.

When you think about your dating experience, is your wife the first person you dated who was a widow for both of you?

For me, yes.



When you think about dating a widow, what are some things that you found that were different than dating experience outside of dating somebody who is a widow?

With Kim, she was, I wouldn’t say more experienced, but it was the way she carried herself. It was different than anyone else that I had dated before. I am not saying that other women were immature, but it was something about her.

She had been a wife.


How about you, Fred? The question is what challenges did you find different dating a widow than not? When I talk about that, I’m talking about emotional triggers and all those different things that you have dating a widow that you may have not dating somebody that doesn’t care about their ex anymore, and those types of things. This conversation has to be as organic as possible.

I’m not sure if I had any challenges. My mind was easily adjustable because I was aware of the fact that you were a widow. The way you were and your personality, I didn’t think I had to tiptoe around stuff because we were talking. When we were talking, it seemed very organic. We talked and it was very relaxing. You talked about it openly, so it wasn’t like I had to worry about stepping on a landmine or anything like that by mentioning it inadvertently that it was going to upset you. You were processing it and you were speaking about it on your own.

You bring up a good point, which is talking about it. When thinking about dating a widow, when you first hear those words, are there things like, “They have a dead spouse. How are we going to approach that?” Are you looking for that person to lead you into that?

I didn’t think about it that way. I thought initially not overly much either. I was like, “We’ll see how it goes.” The way your demeanor was, it was like, “Okay.” When you mentioned it, you didn’t like to fall apart, start crying, and all that stuff. You were speaking about it because a little time had passed. It didn’t seem like a sore spot or a pressure point.

It wasn’t like you’re always tiptoeing around it like, “Don’t mention it,” and all that stuff. That was probably the long way to making it relaxed or more natural because I didn’t have to worry about triggers like me doing anything. You had triggers that I found later, but that was normal. It was on certain dates or whatever. That was easily understandable. It wasn’t anything unreasonable. If somebody had a reasonable expectation, it might have been a problem, like they expect you, for some reason, not to mention or think about your former husband at all. That is ridiculous. I would think that way. It was all right.


For me, it wasn’t a big deal because I didn’t think that initially, the two of us meeting was one of those love-at-first-sight things. We were out to start a new relationship. Kim would say that I was a booty call. She had a boyfriend at the time. I didn’t have a girlfriend, but there was somebody that I was possibly interested in. For the both of us, it was a hookup. She was thinking more so, “I’ll get what I want from this guy. He’s going to pay some of my bills,” and all this stuff. Little did she know, I wasn’t going to pay anything. Not me. I was the wrong one.

It materialized because when we first met, we met each other, saw each other, and then there was a lull. We went on doing other things and then we, in passing, saw each other again. That’s when we started dating. When she told me that she was married before, it didn’t matter to me because I wasn’t looking for anything long-term. It wasn’t a big issue.

When I first started dating after Mark died, I started online. I did that because it was easier for me, the idea of talking to another man. I had never thought about doing that. I had men tell me, “If we’re going to date, then you can’t be talking about your husband,” or, “If you’re not over him, then why should you bring him up?” What are your thoughts on a woman telling you that and they’re dating and knowing that they’re a widow?

That wasn’t an issue for me. Kim, in our relationship, said, “There are going to be times when I may be thinking about him and it may draw up some emotions.” I said to her, “If you bring it up and cry, I’ll be there to cry with you.” That was one of the selling points for her saying, “I got to keep this dude.” It was no big deal. I knew she was going to be thinking about him. It wasn’t an issue for me because I’m here now and I’m here to support. That was no big deal for me.



What are your thoughts on that same topic, Fred?

Similar. We talked about i, too. To me, it would’ve been a red flag or abnormal if you never mentioned it because, one, you have children together. You were together for 30-some-odd years. To not mention that part of your life at all, mention him, or not have any dates remind you of anything, to me, that would be like, “Something’s wrong here.” Either you’re hiding stuff or you don’t care, which means that’s not the kind of person I want to be with anyway because you got some mental issues I don’t want to be getting into. It’s natural. You’re going to do that. I have an ex-wife too. You have kids together and there is stuff that’s going to come up. It doesn’t mean everything else stopped. It was nothing unreasonable.

You say unreasonable. Some people think the existence of that is too much for them to bear. What about your personality or confidence that didn’t make you feel like it wasn’t a threat or something to make you feel uncomfortable?

Not the way things turned out. If there’s some reason that you’re trying to get me to conform to be like Mark, then that’s a whole different ball game. That wasn’t an issue. I was looking out for that but not in a big way. It was like, “I’ll keep my ear up,” but that didn’t happen. That would’ve been something we’d have to discuss because I’m not going to change to be somebody else. If you don’t want me for me, then that’s not going to work out.

Speaking about conforming to Mark, what was that one thing that you dropped on me that is very similar to Mark?

It is probably more than one thing, but hunting.

How did that response go when I found out you were a hunter? I know that was weird when I was asking you about that. We were at your apartment. You said you were a hunter, and I was like, “Let me see your hunting gear.”

I was like, “All right.” The way you said it, I was like, “You don’t believe me?” I was like, “Why would I make up being a hunter?” I was like, “All right.”

I had him bring out all of his hunting gear.

Hunting license and all that.

When he said, “I hunt,” I was like, “What kind of hunting?” I was like, “Let me see your hunting gear.” He was like, “Okay.”

It was a weird thing. Nobody would make that up.

That wasn’t what I was talking about. I was talking about when we were in a restaurant. You were in your uniform and I found out about something.

My middle name. My middle name is Mark. She was like, “Who?”

He hunts and fishes.

It was quite a while. You intentionally didn’t tell me that for a little bit.

I don’t think that was intentional.

Your middle name is my deceased husband’s first name.

It came up not too soon after we started dating. I wasn’t hiding it from you. My mother’s name was Tina. That took me more aback than anything at first when you told me, “My name is Tina.”

You can’t be kissing me and thinking about your mama.

We hadn’t met yet when you told me your name. I was like, “Well.” I thought, “Do I want to go forward with this at all? Is this going to be too weird?” I had to think about it for a bit. I was like, “Eh.” That was weird. My mother’s name wasn’t Tina. It was Louise but everybody called her Tina or Tine. It is the same thing. When she said her name was Tina, I was like, “Maybe it’s not her real name,” but it was her name. I was like, “All right.”

Four letters. That’s it.

That was a little bit of like, “It’s all good.” I told my kids about it and they were like, “What?” That was probably the biggest thing for me. It was the Tina thing.

I didn’t think about that. It was the Mark thing for me. In my mind, I was thinking, “If I ever yell this out in a passionate moment, then I’m still calling technically the same person.” I’m clear about that. It’s not a problem at all. I’m calling you by your middle name. What about you, Lionel? Is there any part you talk to other male friends and they say, “How are you going to feel if they talk about their ex?” People say ex, but it’s your deceased husband. There are more memories. There is more of a relationship. This is a relationship that ended not because you wanted it to but under extenuating circumstances. Kim’s husband was killed. They were high school sweethearts and got married. Kim and I will talk later. I’ll let her speak more about the details of that. You never felt like you were living in the limelight of her deceased husband or feeling conflicted about that.

I didn’t talk to anybody else about him. I have friends, but it’s not folks I’d call up and say, “I’m dating a young lady. She’s a widow.” It even got to the point where it didn’t bother me at all that she talked about him. Still, she tells me that his stone marker or grave marker, the numbers are triple four. Wherever we go, if a car passes by and there are triple fours on the license plate or I wake up in the morning and look at the clock or look at my watch and it’s 4:44, I’ll say, “It’s 4:44.” It’s like a game, but it’s a reminder because she will say, “There are triple fours.”

It doesn’t bother me at all. That was her first love. It’s not anything that I have to compete against because she’s with me. It’s not where she has ever tried to conform me. She has never held me to try to meet his standards or anything like that. We’re two different guys, so that’s never been a big deal or a big issue.

WRT 30 | Dating A Widow
Dating A Widow: That was her first love, but it’s not anything that I have to compete against because she’s with me now.


If I hear what you’re both saying, if you’re dating a widow or you’re dating a widower and this person is trying to conform you to their deceased spouse, that’s something.

That’s a flag.

That’s a flag that we should talk about. Even though it was a booty call or we were not, what if Kim or I did that? How do you think you would’ve approached that conversation?

For me, that would’ve been a turnoff. It would’ve been a conversation behind, “I can’t be him. I’m not trying to be him. Don’t try to conform me to him.” Let me take you back. When Kim met me, she had a boyfriend. They broke it off after that. I remember there was a time when she bought me a pair of shoes. She gives me this box. I open it up and there is a pair of shoes in there. It was slip-on patent leather, little pointy shoes.

I’m like, “What is this for?” She’s like, “I’m buying you some shoes,” but these were the type of shoes the boyfriend wore. I was like, “I don’t wear shoes like that.” I told her, “I wear Stacy Adams.” She was like, “Stacy Adams? Tell me about Stacy Adams.” After that, that was all she ever bought me if she bought me shoes. I don’t think she was trying to conform me to her boyfriend. She assumed, “He liked those shoes. Maybe he would.” That wasn’t my style. I have a different style than what that guy wore. She wasn’t trying to make me out to be like him or whatever. It’s a mere conversation like, “This is what I like. This is the style that I have.” That squashed it.

Earlier, you spoke about triggers. What are some things that you’ve seen at certain dates or certain times in my behavior? How have you had to manage that?

Certain holidays, Christmas, Mark’s birthday, your wedding day, or the day he died, stuff like that pops up. First, I didn’t understand. I didn’t know those dates. When your behavior changed, I didn’t understand what it was. I thought you were having issues. I tried to be respectful of it but then you told me what it was. I try and keep a lookout for it, but I even more understand what it is. It’s not an issue. I try and make things easier for you if I can and go from there.

When you say my behavior changed, what are some things that you’ve noticed?

Sometimes, you get sad or down. That’s not your normal state. Some things would upset you that normally wouldn’t. It is nothing unexpected.

I’m asking those questions to describe it because somebody else may be wondering, “They say they’re happy with me and we’re married, but then, I noticed they behaved like this.” That’s why I was asking.

For you, it was very mild. You thought you were more demonstrative than you were. Sometimes, you would start crying, but that was not in the majority. When you told me what it was, it was like, “That’s understandable.” Sometimes, you would apologize for your behavior and I’d be like, “What are talking about?” For you, it is more demonstrative than it is for me.

It’s nothing unusual. You explain what was going on. I didn’t have to pull anything out of you. You would catch yourself and explain it. I’ll say, “Okay,” and we talk about it a little bit. I try and be aware of it. The dates were coming up and we deal with it as it comes. Certain things are more triggered. When the dates are coming up, you’re more worried about your children, especially your daughter, than yourself. That played into getting you more upset because you’re worried about her. I keep saying reasonable, but to me, that’s normal. That’s the way things are supposed to be. To me, it would be more of an alarming signal or red flag that blew all that stuff off and nothing ever popped up. That’s not normal.

You say the word normal. I want to try to always unpack what that looks like. A lot of people would say, “I don’t know if I want to date a widow or widower because they’re going to come with all this extra baggage from their deceased spouse.” Lionel, you talked about comforting Kim or being there. Not those words, but how would you describe what that looked like? What were her emotions that gave you a clue that you needed to be supportive?

It was like Fred said. She told me from the beginning, “There are going to be times when his birthday comes up, our wedding day, or anniversary times that I’m going to be sad.” I gave her her space like, “If you want me to be there, I’ll be there to comfort you. If you need your own space to where you need to go and process it, I’m going to give you that time, but I’m still there for you if you need me.” She laid it out.

There were those years when it happened. As time went on, we’re bringing up, “Today is Lafayette’s birthday.” That was pretty much it. It wasn’t a time that we were mourning or anything like that. It’s a normal day. She doesn’t dwell on it. She doesn’t get sad. It’s letting me know, “Hey.” I don’t keep up with his birthday, their wedding anniversary, or that kind of thing, but she’ll let me know that it’s that time. The time for getting sad and stuff, that’s gone.

It takes a great deal of confidence in the person who’s dating the widow or widower to know where they are seen in that relationship. If not, a lot of those reactions that you talked about would be responded to differently. What do you think? Did you always think you had a lot of confidence in the relationship?

It takes a great deal of confidence in the person that's dating the widow or widower to know where they are seen in that relationship. Share on X

I thought I did. She helped me with it also. Kim is very supportive in so many ways of making me feel comfortable around her or whatever. She is always supportive. She has never been one to compare me to him or anything like that. It’s just me. I’m the one. It’s never been a big deal.

What about you, Mr. Jackson?

It’s pretty similar. I may have approached it a little differently. I was determined that because of some past experiences, I was not going to let somebody bend me the way I didn’t want to go. There are certain things that are going to happen that I can go with the flow and adjust to, but I do have a hard line. If you’re trying to make me that person, make me conform to that person’s image, or criticize based on something that a person used to do, that was unsaid. That wasn’t going to work. That would be like a,
“We’re done.” That was it.

We dated for a long time. There were things I was looking for and being careful with. It wasn’t the widow stuff. It was general personality stuff. If at any time I detected that was going to be a real issue even after a couple of conversations, at a certain point, I’d be like, “If this is not going to change, then I’m going to go elsewhere.”

I wasn’t pressured because I already had my plan in place or my certain limits set. I didn’t dwell on it. It never was an issue. I’m trying to be conscious of like, “Something’s coming up right now,” or you’ll say something and I’ll say, “Okay,” and then we go from there. Your reactions have gotten less, too. More of it’s targeted toward Catherine and Alexander than yourself. You’re worried about how they’re doing.

I never thought of it that way.

I’ve seen that be the change of focus.

You two have the perfect dating experiences with the widows.

It’s not perfect.

I learned from experience where I was like, “At this point in my life, I need to look for this. It’s non-negotiable.” Certain things are non-negotiable, and certain things are. Once I had my plan in place, then it took a lot of pressure off me in certain ways. I know, “Here are my limits. Here’s my line.” If something is too far over that and it’s an unsatisfactory situation, then it’s easy. Plan B. Go that way.

That wasn’t predicated on being a widow. That was about dating women in general.

The whole package. That was another aspect that was in there. It had nothing to do with my limits. Like in a box, you had your stuff in the box and stuff is going around. You’re like, “All this stuff’s acceptable. It never crossed too far over here.” It didn’t trigger any negative reactions. Everybody’s got baggage, but different kinds. It’s different.

Everybody's got baggage, just different kinds. Share on X

For me, dating a woman with children was harder than dating a widow. I don’t have any children and I’ve never been one to want any children besides your children. That was more difficult than dating a widow. That’s another story.

That was one of the things I had, too. I was like, “No children that are not adults.”


If a woman had children that were not adults, to me, that was like, “I’m not even going to start that.”

You mentioned children. This is going to be unique to you. What did you think about my children and their dad no longer being here and how that would impact you in this relationship?

One, they were adults already. They weren’t living in the house. They were already out on their own. That box ticked. My thing was even if they didn’t like me or as long as there wasn’t any overt hostility, then I could deal with that.

You did think about that?

Yeah. You have to. I would have to, out there. I did that. That was fine. Other people say, “It doesn’t matter what the children think.” It does because they’re part of the family. If there’s friction from one end, there’s going to be friction in generated other places. I don’t want to have that going on. I also was seeing during the time how things interacted and whether it would affect us in a negative way. It didn’t. I had my criteria set, so it was right along the line.

If there's friction from one end, there's going to be friction generated in other places. Share on X

I’m going to flip this a little bit. Lionel, I know you don’t have children, but you have been invested in my life for a long time. When you were dating Kim, I knew you then. Mark’s death impacted you heavily. What was the thought when you came to your mind when you thought about me dating and what it would look like or when you met Fred? Was it like the big brother coming like, “We’re going to see what this is about.” How was that for you?

Tina is different. For men, when they lose a spouse than a woman losing her husband, it’s different. Women tend to cling to that whereas men, it’s not long before they’re going out trying to find someone else or start dating. Not trying to go out and find another wife, but with you, like other women, it’s a process. I could be wrong. I don’t know what women think if it’s like, “I’m cheating on my husband if I go out and find someone else.” I don’t know what women think, but it takes longer or they never go out and find anyone else. It’s different.

When it came to you, it wasn’t a, “I got to check this guy out to make sure he’s the right one for Tina.” Tina, do your thing. If you want to go out and find someone, I’m happy for you. I hope that you find someone not like Mark. I’m not saying that you find someone better than Mark, but I hope that you find someone that you’re happy with. That’s the key. I’m not the one that’s going to say, “This dude is a nut. I saw that dude hanging out somewhere.”

Fred was cool. We hit it off from the start. I thought he was a nice guy. He’s a nice guy. It wasn’t that I was going to be the overprotective friend. I was happy for you. Even if you had started dating sooner than you did, I wouldn’t have had anything negative to say like, “She got out there fast.” This is your life. I’m happy for you.

That’s fair. One thing I’m not sure if people know is that Mark, his family had a long line of heart conditions. One of the things that made dating easier for me is that he said, “When I’m not in this world, I want you to be happy. I want you to find somebody else.” I remember telling him, “You are up too late at night. I need you to go to bed. You are watching TV.”

When it happened, I was like, “What a gift that he gave me to say something like that.” A man is not ever wanting to think about his wife being with someone else when you’re happy with them. For him to tell me that, thinking of his own mortality and where that would go, and then being able to do that is a lot. This is a question I haven’t asked you. Since Mark died, how have you felt as far as your role with Catherine and Alex?

It’s not that we talk all the time. Alex called me on Father’s Day and wished me a Happy Father’s Day. I wasn’t available because when he called me, it was during church service. I called him back the next day. We were out in California on a cruise. We did not go to SeaWorld because Catherine was in pain. We went out and hung out with her. Every now and then, she would text me and say, “Uncle Lionel,” and ask me something. I know I’m their godfather. We talk, but it’s not as often.

You’re like a pseudo-dad.

Exactly. I asked Alex. We do that food program, the pantry. I asked him, “If you need some food, come on around.” He said gets something, one of those delivery food services or something. He said he was good.

When Mark and I made that decision, the children were small. Even when we moved to Pennsylvania, they spent an intimate amount of time coming back to visit with you guys even as annoying teenagers. It is having those relationships. Fred, to me, being able to communicate is key. People say communication is a big thing. Both of you said that whether it was myself or Kim, we laid out what our expectations were. We were honest with you to tell you what it’s going to look like.

It’s not just communication, but genuine communication. People will communicate, but a lot of times, they’re not honest in that communication. They set things up or say things they want you to hear, but not really what they want or what they expect. That’s the difference. That’s where it was a big difference. You were honest about what you wanted. We had a lot of conversations and you asked a lot of questions. I asked a few. We got things to where it was like, “That’s good.” We got things out.



I want to be clear about this. Fred would wake up every morning. Go ahead. What would happen every morning when you got on your phone?

There is a laundry list of questions. It was like a pre-flight check-in every morning. It was like, “Ugh.” I am no good until I get coffee, so it’d be hours before I respond to that. I have to get coffee.

It was not hours. He would wake up and say, “Good morning. Give me a little bit to answer this.” It was at least 3 to 10 questions.

It was some stuff.

It was every day for almost three years.

The text questions got a little bit less. The question wasn’t reasonable. I wake up on the list because you get up at 4:00. The questions would be there when I wake up, even when I had to go to work and be at work at 5:30. I would wake up, roll in the clothes, and go. The questions are already on the list. I’m looking at it with one eye. My brain doesn’t work until after a couple of cups of coffee anyway.

What did you think about the questions?

At first, it was like, “Okay.”

You thought they were going die.

I figured they would die out but they didn’t. If I didn’t remember to answer them in the text and later on in person, it’s like, “You never answered my questions.” That was good though. We got information out and sometimes. It’s probably not as good as letting stuff out as I should. You give me the safe stuff or pull stuff out. Sometimes, it’s answering your questions, which is good. We have to do that because if you have things you want to answer, then I’m supposed to answer them.

Talking about communication, we met online. We met on the dating app, Zoosk, and we went to Cafe Stella. It was saying, “This is not a booty call and not a hookup.” I wanted to know if there was chemistry.

That’s the whole point. It’s to meet.

It’s to be able to do that.

We sat down, had coffee, and talked. It was a good conversation.

On the second date, it was like, “Okay.” We both talked about where we saw this going and what this would look like. That communication was very clear. How long in that process before you felt like it was genuine though?

I thought right away you were being genuine because of your demeanor. I didn’t think you were trying to put anything on. It’s a matter of me or us having enough back and forth to start filling in blanks and seeing who each other was. I didn’t think at any point you were being phony because that would’ve been another red flag. I was watching for that. If I picked up that there’s any kind of phony stuff going on, to me, that would’ve been like, “I’ll hit the eject button.” That’s the way I was. I was hypervigilant about that. That was something I was watching out for. I told you that I was hypervigilant about that kind of stuff, but I never got that sense from you.

I’m going to ask you one more question and then I’ll ask one for you, Lionel. Lionel mentioned dating somebody when he met Kim. Were you dating somebody or seeing somebody when we first met?

It was not that I was dating in general. It was somebody else I was seeing casually, but there wasn’t anything serious going on.

Lionel talked about how Kim carried herself differently. Did you find that with me having been somebody’s wife? How did that show up to you?

I didn’t associate it with having been somebody’s wife. I associated with your personality. I was looking more at your personality and the way you acted. It was not a reflection of you being someone else’s wife. That’s who you were then. You were on your own. I was looking at the way you were. I was trying to take that in honestly, not shade anything of my own into it, and looking at who you were. That was another thing. That’s why we took our time. We agreed to that. There were things I had to see for myself and work out in my head that was like, “This is who this person is and I trust this image.” That was an important part of it.

WRT 30 | Dating A Widow
Dating A Widow: I was looking more at your personality and the way you acted, not as a reflection of you being someone else’s wife.


How long in your dating experience with Kim did it go from the hookup to like, “I could see this being something more.”

We met at a military conference. It was in civilian clothes.

We got to talk about that.

At the time, I was an officer. I was a young officer. She was enlisted. She didn’t know who I was. When we got to the conference, everybody was in their classes. The classes were broken down in alphabetical order. Kim’s last name started with a T. Kim got there late. She wasn’t the model soldier, let me say that. She got there late. We had room in our class, so they put her in there. She went around the room looking at who was in there and looking at the guys. We locked eyes. It was like a, “Hey,” thing. She was getting up, being disruptive, pouring me water, and all this kind of stuff.

She didn’t tell me about that.

Lady was telling the instructor, “You need to go sit down and stuff.” She asked me if I wanted to go to lunch because I didn’t know anybody there. We had a mutual friend who was in the group and she had asked her who I was. She said, “He’s a lieutenant. I know him.” She was like, “He’s an officer?”

Break down what that means, the officer.

The officer enlisted thing and the military are not supposed to hook up. It’s fraternization. We were in the same battalion or unit, but we weren’t supposed to be intermingling. We were in civilian clothes, so we didn’t know. I had never seen her before. She knew a lot of the folks in the class. I didn’t know anybody.

These two are lowkey.

I’m going to say this. She said, “Would you like to go out to lunch with us?” I was like, “Okay.” She said, “What do you like to eat?” I was like, “I don’t care. I eat anything.” She was like, “You need to watch what you say.” That was the thing. The way you carried yourself as a widow, Kim didn’t carry herself as a widow. Kim was out there. She cursed. She drank. She probably smoked weed. She was wild.

Kim was mad though. We’ll get into that.

She was hurting.

That’s something to talk about. Kim’s husband was killed accidentally on a military training exercise. They came to her door. She was there by herself and they said Lafayette was dead. She was shattered. She spent a great deal of time being mad at God, being mad at any dude. She was trying to use that as an opportunity to whittle her way through that, go through that, and try to cure her pain. We were in two different places and phases of that idea of being a widow or that phase of our life. I had children. Mark and I together were 32 years. She and Lafayette, I don’t even think got to five. It was 3 or 3 and a half.

It was a year or so.

There was so much that was ripped from her.

She was young. She was in her early twenties.

I was in my fifties. It was horrible. She spent a lot of time trying to find herself through that misery, doing through dues and everything else masking her pain versus being able to deal with it. It was coated with a lot of stuff.

She didn’t want a long-term relationship because she was getting military benefits from his death. If she married somebody, she would lose those.

That’s a lot to talk about. People choose that they don’t want to commit. Also, the idea is probably for Kim to get married again and the husband would die. It is the pain and agony of that.

That’s possible.

I’ll circle back.

She did all these things. I was the booty call. From the time we met, we may have gone out or something like that and then it fell off. I was in the process of meeting someone. She had a steady boyfriend in college. It was one day. Some time had gone by. We were running PT. We ran PT in the evening. I was running and saw her coming towards me. I was like, “That’s Kim.” We passed each other and were like, “Hey.” That was when the PT uniforms were fitting. When I looked over, I was like, “This girl’s dragging a wagon.”

She’s still dragging that wagon.                                                                                                                

It was a little wagon back then. I was like, “Wow.” We started calling each other and found out that we lived less than a mile and a half from each other. I used to ride my bicycle around to her where she stayed. She lived with her sister and they had another roommate.

I heard about that.

We would see each other. We’d go out. Kim would meet other guys if a guy wanted to take her out or something like that. It started getting to the point where we were seeing more of each other. The one girl that worked where I worked, I wanted to be intimate with her. Kim was always there. She was blocking. It was like, “Aren’t you going to Philly to see your mom or something?”

When the time came or when the opportunity came, Kim left and it was like, “This is it.” She came over and it was getting down to it, but I was thinking about her the whole time. Nothing happened. The other young lady was wondering, “What did I do? What’s wrong?” I was like, “There’s somebody else that I’m interested in.” I was thinking about her the whole time.

When she came back, she was already in the mindset of, “I’m done with him. He doesn’t know what he wants to do.” That’s when I asked her out. We went to a restaurant called Quincy’s. It was on Denby Boulevard. It’s closed. It’s still there, but it’s all boarded up and stuff. That’s when I asked her to be my girlfriend. I said, “I want a relationship with you,” and it went from there. The good thing about Kim is she has always been a communicator. She didn’t wake up in the morning with a list of texts, asking me a bunch of questions, but she is a big communicator.

We weren’t even texting then when you and Kim were dating, so that’s not even fair. If it was, my girl would’ve had a list.

We communicated a lot. I was the type that I would shut down, but she would not let me do that. It was “We need to talk about whatever.” That’s her. We fix whatever the issue is right then. She had said something to me that I didn’t appreciate. The next morning, she was like, “I know something was wrong.” We always agreed we wouldn’t go to bed mad about anything. I wasn’t mad, but I didn’t like what she said. She said she was saying it in a joking way, but she let me know, “I know when something’s wrong because there are certain things that you do to me.”

If I’m understanding you correctly, dating a widow is not something to be afraid of.

Not at all. That was never a big issue at all.

For you, Fred, would you say the same?

It’s similar. I never thought about it. To me, it depended on who you were and the way you acted. Everybody’s not the same. Some people are dysfunctional about stuff like that. Even if they’re not dysfunctional, it’s whatever behavior they had or who they were that wasn’t acceptable to me. If they’re not acceptable to me, I’m going to move on. It wasn’t like, “I’m going to make you act differently.” I didn’t want you doing that to me, so I’m not going to do that. It was a matter of keeping the stress down. It was like, “We don’t have anything invested in each other yet. We’ll learn. If it’s not something that’s right, then I’ll move on.”

For me, as the widow dating in my head, it seemed like a big thing. Maybe it was from the people that I engaged with beforehand. For me, it was the idea that one, Mark was White. Whether I was talking to somebody European or somebody African-American, it was a big thing in their head like, “What did your dead husband look like? Who was he?” There were initially a lot of questions that seemed off-putting to me wanting to know what the competition would look like.

It sounds like insecurity.

Did either of you ever feel like the deceased spouse was a competition or something you had to measure up to, whether it was sexually, emotionally, financially, or anything like that?

Never. For me, it was never one of those things like, “How was he in bed? Am I better than him?” I couldn’t care less. I’m trying to do my thing. It was no big deal. It was like dating somebody who had never married before. It was no different. That was never anything in the back of my head like, “Am I going to be able to meet whatever he did or compete with him?” I wasn’t trying to do that. He’s not here anymore, so it’s just me.

What about you?

It’s the same. Right away, even before we met, it was like, “What do you do?” and I told you. Financially, it wasn’t an issue because you already knew upfront. I was a police sergeant, so I didn’t make as much as an electrician. That was like, “I’m cool.” If you’re not, then we wouldn’t have started. That’s why I’m not trying to hide anything. It’s like, “This is what you got. No surprises.”

I’m going to have to find some people who are dating widows who are having a challenge because the challenges you’ve had in dating are regular dating challenges. It’s not so much that is a widow-centric scenario. I will ask a couple of other things. Can you think, Lionel, of the most triggering experience Kim had about Lafayette and how you showed up for her? It could be emotional or something that was hurt, sad, or emotional about Lafayette, or it didn’t exist.

For me, it was the situation that happened and how it happened. Early in the relationship, when that anniversary would come up or the day he died, or his birthday, those are only things. That didn’t last a long time. There were a few years that she would get sad but not to the point where she was locked in a room, crying or something like that. It happened. She was sad. It’s normal, but that’s about the only thing. It was nothing that was a big incident or something that sticks in my mind like, “That happened.” Nothing.

I appreciate that you both have talked about how it’s normal. The idea that this person is going to miss this other person has nothing to do with how they feel about you. It’s about how they feel about this person that they’re grieving. Their grieving doesn’t mean that they don’t have space to love somebody else. Oftentimes, people are thinking that because someone’s a widow or widower, “They’re going to half-love me.” Have you ever felt half-loved?


WRT 30 | Dating A Widow


No. The other thing is she introduced me to Lafayette’s mother. She would call us once a week. She would call and talk to me. We would go visit. She treated me like I was her son. We had a great relationship up until the time that she passed. Every time we’d go to Philadelphia to see her family, we would stop and see her and spend time with her. There were no issues with anything.

This is the question for both of you. Sometimes, I hear that if someone’s thinking about being with a widow or a widower, they feel like they’re going to be half-loved. They’re not going to feel like that person is committed to them. They feel jealous or feel some kind of way. If those thoughts came to your mind, what did the other person do to make you not feel that way?

I’ve never felt that way. The thing was Kim introduced me to Lafayette’s mother and she welcomed me with open arms. She would call and talk to us every week. When we were gone on a trip or something, she would call looking for us like, “Where are you two? Are you on a cruise?” We would always let her know when we were going somewhere.

When we visited Philly to visit Kim’s family, we would always go spend time with her. I met Lafayette’s brother. He was cool. As a matter of fact, he was even in the area once and contacted Kim. He was down the street and we didn’t know he was coming around. He visited us before. They’ve always made me feel welcome. It was never a competition thing or I was trying to do more to outdo him. He’s not here, so it’s just me. I can be me and do whatever I need to do to keep her happy. That was my goal.


WRT 30 | Dating A Widow


Mark’s family is not close, but in the place of that, it would be my intricate friendship group that would be similar to that. Did my friends make you feel welcome? How did that make you feel, entering a group of friends or my family and knowing that? How was that for you?

Your friends made me feel welcome. I didn’t have any issue with that. Nobody was standoff-ish or nobody acted weird or anything. It was the opposite. You do have a big network of friends. Gigantic.

Do you remember when we met?

Go ahead. You remember better than me.

We were at Fort A. P. Hill at the rifle range. You were in the foxhole next to me. It was A. P. Hill.

That’s where we went.

That’s when I first saw you. I don’t even know if Kim and I were together then. You two probably knew each other.

We were in college together. I saw Kim at Reserves. It was like, “Hey.” When you’re not in uniform and you’re in clothes, you look different. I was like, “That’s the same chick that’s in my unit,” so then we started talking. I knew Kim. When she started dating you, I knew about that.

That was when I first saw you and we talked. I thought you were really nice. I loved your complexion. It was like, “That chocolate girl over there, you couldn’t shoot worth a dime.” That was it. I don’t know how we met with Kim after that.

I knew her before you guys were dating. We had a friendship involved with that. It evolved over time and the connection of it all and things like that. I remember when you guys were getting married, being at the house, and putting everything together and all the stuff. There were cake toppers. Lionel liked a chocolate girl and you see Kim. They have these cake toppers and we’re looking at stuff. Lionel was like, “Who’s that?” I was like, “That’s you.” He said, “I’m going to need to fix that.” I was like, “Kim, what is he talking about?” He got some paint and made Kim darker. Her cake topper, I was like, “Boy.” He did fix it.

It looked more like us.

That’s when we started creating our own relationship.

Before, everything was me, you, Kim, and Mark. You and I started evolving and having a friendship that is separate from Kim.

Do you remember you put a party together for her? Do you remember when she stayed in the apartments across from Beachmont? You put a party together for her. It was a little surprise thing. I remember it was you, Mark, and a friend of mine who was in town. She lived upstairs in that apartment. We had a little party for her. It was for her birthday.

I love that you two have found out how to navigate something that you say is normal that other people are extremely fearful of.

It has got to be some personal insecurities for people to feel that way or feel that they have to compete. They want to know all this information about your former husband or spouse. Whether it’s a man or a woman, if you are asking all those questions, you have some personal insecurities. That had never crossed my mind.

That’s like when people want to ask about people you’ve dated before. They want all these details about other women I’ve dated. That doesn’t have to do with anything and vice versa. I compared some bad experiences that I had before meeting you. That was like, “This is fairly normal,” or I was already prepared. I’ve gotten myself together where I was like, “I need to have myself in order first.” That’s what Lionel said. There’s probably some insecurities on other people’s part where they want to dig into all this stuff where they have to know all this stuff. What does that have to do with it? That is unless you’re trying to model yourself after that person for some reason, which is not either.

That’s strange.

We’re going to focus on this part if you’re dating a widow. Don’t get bogged down in the details of who their deceased spouse was because it’s not going to serve you well. They are deceased. You are the person that’s in their life and having this dating experience.

If you're dating a widow, don't get bogged down in the details of who their deceased spouse was because it's not going to serve you well. Share on X

That’s me. That’s how I feel about it.

For some reason, it becomes a sore point because they’re not handling it well or they’re bringing it up in an unhealthy way or off-putting way. You move on to something else that’s going to be a little bit more satisfying and not so contentious or whatever. If that person’s not ready to date or maybe they never process it properly, they never will. That’s not something that you can do for them.

Fred, this is the same question I asked Lionel earlier. Can you think of what was maybe the most emotional or triggering moment I had and how you had to show up for me?

Yeah. It was the first year we were dating. A date came up. I don’t think we’ve been dating that long.

I want to say it was about six months or so.

I can’t remember what day it was. A date came up.

It was my one-year anniversary of living in Virginia. That is what it was.

You were emotional. You were crying and upset about stuff that was not normal. We talked about it and you told me finally what it was. It was like, “That’s not unreasonable.” You explained it to me and we dealt with it. We went on from there. You’ve had other dates that were similar. It has gotten less over the years. It has gotten less as far as certain trigger dates, like birthdays or some dates. It was some date that popped up and you said, “We shouldn’t have had it on this date.”

My birthday. We got married the day after my birthday. That seemed cute when we were in our twenties. Since he is not on this earth, when I am thinking of my birthday, I would automatically start thinking of our wedding anniversary, which has no significance to me. It took a while in therapy, talking, and going through that process.

It has significance. It’s a reminder of change. That’s something that’s not as big a deal. It’s expected, but you seem to be processing it better. It doesn’t make you break down. Even if it did, it’s not like it’s an unreasonable situation.

Even with Kim, she told me the story or the situation of how it occurred. I’ve heard it a couple of times. It wasn’t something that she was talking about all the time. She told me about it but she didn’t harp on a lot of things or a lot of situations or incidents with her former husband. It wasn’t always his name coming up for something or comparing me to him or anything. It was never that.

When you started dating Kim, were there pictures of Lafayette up in the house?

There were pictures.

How did that resonate with you?

I saw what he looked like. He was a good-looking guy. Back then, that was when everybody was into the Puma warmup suits, Run-D.M.C, and all that kind of stuff. He had his pictures where he had his Kangol hat. That was it. Even if she had them out, that was no big deal to me.

You say that, but I have spoken to widows or widowers. People don’t even want to come into the house and date them because their deceased loved one’s pictures are still up. They don’t want that to be a focal point. They say, “You’re not ready because you still have their picture up.”

I’ll give you an example. If I was gone, when you come into our foyer, there are all those cruise pictures. To some people, those got to go right in order for me to come in here. That would’ve been no issue for me.

I was going to say that. That’s strange. It’s like when you have kids together so you are not allowed to talk about your kids or you’re not going to have your kids’ pictures out. That’s something else that’s weird to me. People do worry about that. That’s a negative issue that you need to work out because that’s unrealistic. That’s a big chunk of your life or an important part of your life. How are you going to edit that out? If you’re going to do that, then that’s also something wrong with that, too. If you’re going to forget about all that stuff to be with me, then there’s something wrong with that, too. That’s not going to work.

WRT 30 | Dating A Widow
Dating A Widow: If you’re going to just forget about all that stuff just to be with me, then there’s something wrong with that too. That’s not going to work.


For somebody to act like that, that should be a flag. You are bringing those insecurities into our relationship.

That’s not going to be good.

That is not healthy.

That right there is one of the reasons why I wanted to talk to both of you. People may have been expecting, “Where is the difficulty? Where’s the challenge?” Kim and Lionel’s marriage, fortunately, was a good thing for me to model as I’m in that situation being a widow and understanding how a man can show up for you and not make it a hindrance.

The thing when you were talking about where Kim said that you showed up for her and that made her say, “Let me lock this guy down,” on the one-year anniversary of me living in Virginia, that was my moment with Fred. I remember it because I was more emotional. It was the first Something in the Water event down in Virginia Beach. Yolanka, Fred, and I went down there. It rained out the first year. We wound up going to Cooper’s Hawk to eat. Yolanka went home afterward. Fred and I went back to my townhouse for a bit before he went home.

I was in the kitchen in the little townhouse I was renting. I was getting a glass of water and walking back to him. I was standing there frozen and I started crying. That day was the one-year anniversary of living in Virginia. Mark had already moved here. I was planning to move here. The idea of being in Virginia was something we were excited about. Everybody was looking forward to us coming back. The fact that he was dead and this guy was in my house, and this is a house Mark’s never lived in. all that stuff started waving over me. I was standing there and I was crying.

Fred came over. He was trying to look for a glass that got broken, like, “Did you drop something? Is something going on?” I said, “You seem like a nice enough guy, but this is the one-year anniversary of my living here. This is not how I thought my life was going to go.” What he did was take the glasses out of my hand so I didn’t drop those and put those on the counter. He said, “Do you want me to hug you? Do you want me to leave? Do you want me to stay? Whatever you want me to do.” You said, “You never have to feel bad about missing or loving your husband because you never planned on this happening.” I was like, “We’re here now.”

That’s not something you put on a dating app like, “I need you to always understand I’m going to love my late husband,” or, “I need you to have enough confidence as a man to know that I love you, but know a part of me will always love him.” It’s not that everybody’s going to exactly get that, but it is to know it is possible for somebody to show up in your life in this season and accept you for right who you are, support you, love you, and be okay. It is too much of the other voice that I’m going to expect you to take these pictures down. I have talked to widows, more females, about, “Are you still talking about him? Are you still upset about that? Do you have these pictures up?” For them to say, “If we’re going to date, you got to get rid of that.”

It is possible for somebody to show up in your life in this season and accept you for who you are and support you and love you and be okay. Share on X

This is for widows and widowers to know you should not have to subject yourself to someone demanding that you remove that information or those pictures of your late spouse to date. That should not be criteria because there are people that are confident in themselves that will meet you in that spot and love you on that journey.

Both of you do that. I’ve heard Kim talk about it, but this time, it’s like, “I’m in this situation.” My expectations are there because I know that it is possible. Choosing to do that may mean that I may be single because I’m not willing to settle for somebody that would approach me less than. I know that exists, and that was huge for me. That is possible. Mr. and Mr. Lowkey over here.

I’m being myself.

I know you both are. That’s why I interviewed you both together because you’re both lowkey. Guys may not do this, but pretend. If a guy comes to you and says, “I met this widow I’m thinking about dating,” what advice would you give them, Fred? It’s the same to you, Lionel, in a second.

Be yourself. Understand there are going to be issues. You got to be accepting of certain things. Watch out for red flags and see how things feel. Guys don’t do that too often.

Let me do it differently. Your son comes to you and asks if that could happen. Alex could come to you and ask. That’s a more likely scenario for the children that you are fathers to. Nikola or Lexi comes to you and says, “This girl’s a young widow,” or, “Her husband died in the military. I’m thinking about dating her. She has no kids. I know Ms. Tina was a widow. What do you think I should be thinking of or looking for?”

I can sit them down and give them the talk. It’s the same thing. Go through the helping process. Go through the same process of awareness that I came to the hard way. I’d give them my advice on some things to look out for. Don’t let something you pick up as a red flag to you go by without being dealt with. What may be acceptable to me in some respects may not be acceptable to you because of age or whatever.

Don’t expect this person to forget about the other person. Be aware. Don’t let them try and make you like the other person either. To keep things civil or keep things from being too contentious, don’t go along with that kind of stuff. In the end, it’s not going to be healthy. You may seem to be okay at first. You change this and change that, but after a while, it’s not going to be good because you’re not that person. Either they want you for you or they don’t. There might be a few hiccups. Notice everything else, but keep that guide in mind. Stay on that path. If it works out, it will be better in the long run. If it looks like it’s not going to work out based on how you feel, not how they feel, then use your best judgment.


WRT 30 | Dating A Widow


I like that answer. I would say support her in the loss of her husband. Feel her out. Be supportive for the first part. Date as normally you would like anyone else. Don’t allow her to try to conform you to her former husband. Go along with it. If you see anything that’s not going right, you’re going to have to make your own decision and leave. If you don’t and you see this continuing, it’s not going to end well. You need to sit back and see how it goes. Allow her to mourn but not to the point where all she’s doing is talking about her former husband and trying to turn you into him. That’s not going to be good. Support her.

Thank you very much.

You’re welcome. Thank you.

Thank you.

We wrapped up a discussion with Lionel and Fred. I told you that they were both lowkey. I want to say thank you for being here with us on this journey. I am sorry for the person that you have lost that’s driven you to this conversation, but I am glad that you are part of the widowhood. I hope this discussion has been encouraging for you to know that there are people who can meet you where you are. As you start your dating journey with your expectations and criteria of who you’re dating, it’s not too high. You need to be comfortable. You need to make sure that the people that you’re welcoming into your space welcome you. I encourage you to keep showing up for yourself. We’re here for you on this journey. I’ll talk to you soon.

Thank you for viewing this post. I am not a licensed therapist or professional life coach.

I am sharing my experience of loving the same man for 32 years, a mother to two adult children, a retired military officer, a breast cancer survivor, and my connections with others.

Anyone experiencing suicidal thoughts should reach out to a suicide hotline or local emergency number in their country https://www.psychologytoday.com/us/basics/suicide/suicide-prevention-hotlines-resources-worldwide