EPISODE 4: Dating, With Children

Published 10/26/23

0:00:09 – LAURA STASSI
This is Dating While Gray: The Grown-Up’s Guide to Love, Sex, and Relationships, I’m Laura Stassi. For many of us who are looking for romance again after a long time off the market, there’s a new wrinkle, so to speak. “Dating, With Children.” That’s next. 

When you interview a comedian, sometimes you need to take a few moments to let the shtick out. 

0:00:43 – PRIYA
They say the best sperm comes from Denmark, but it’s hard to find a good Danish in Hayward. Nothing but churros and egg rolls here. And I decided to go through fertility treatments. They removed 20 eggs and graded them. They said I had two Grade A eggs, and the rest were boiled. 

0:01:05 – LAURA STASSI
That’s Priya. She’s in her 50s and lives in California. Priya works in the biotech industry to pay the bills. She does stand up to relieve the stress. Over the past decade or so, Priya’s had a lot of it. 

0:01:19 – PRIYA
I was 42 years old, and I decided I wanted to have a baby on my own. So I went through fertility treatments, about three rounds of them, and they weren’t successful and so I gave up. And then I met this younger man, a French guy. I met him on sort of a social media platform, it’s called Internations. And it’s all over the world. And while I was living in Brazil, that was an outlet for sort of the expats that were living there, to kind of get together and meet and stuff like that, and you could meet people on there. And so he signed up for an event that I had also signed up for. 

We just threw caution to the wind, I just didn’t think it was going to happen, and I just decided to enjoy myself. He was nine years younger. It was more of a situation than a relationship. But about a year after dating, I thought it was early menopause symptoms and I went to see my gynecologist. And I said, I’m having these symptoms and I think maybe I need to think about hormone replacement therapy. 

And she said, well, let me just examine you. And she did the exam and stuff and then put the Doppler on my stomach, and we heard a heartbeat. 

Oh, my gosh.

And I was like, is that mine? Because it just didn’t seem like it could have been possible. And she was like no, by the sounds of it, you’re three months pregnant. So my life sort of instantly changed. And I shared the news with his father at the time. But he’s just chosen not to be a dad and not to be in our lives, so it’s just the two of us. 

0:02:50 – LAURA STASSI
I have to love this story though, because, I mean, I’m sure there was heartache involved, but I mean it’s kind of a beautiful thing. We always say people come into our lives for a reason. Maybe his sole purpose was to give you, your son. This French man, even though he left, he’s not in your life, he was kind of like, you know, the little sperm angel. 

0:03:10 – PRIYA
Right. I think so, yeah, and the universe was saying OK, here it is, here he is, we picked him for you. We were all stuck in hibernation during the pandemic, and my family lives in Canada so I couldn’t see them. I had no idea when I would, and I was trying to be a full-time employee, a mom, a teacher, all these things at once. And I was going crazy. And my friends started this virtual open mic to sort of keep our little community together. 

And I’ve always been told I’m funny. But I never had the courage to actually try it because I just was too afraid of the rejection. So I thought, you know, if there’s any chance to do comedy, this is probably the safest form. It’s on a computer. If nobody laughs, it’s no big deal. And so I started doing these open mics. I just started writing some bad jokes, but people laughed, and they kept laughing, and then I kept writing some more. And it really saved my sanity and really sort of helped me deal with everything we were all going through, what I was going through trying to manage the situation and manage my son and help him and try to get through that time. 

0:04:19 – LAURA STASSI
I can’t imagine having a young child at our older age during the pandemic. That must have been so difficult. 

0:04:29 – PRIYA
It’s really hard because you’ve got to deal with all the changes you’re going through in aging as a middle-aged person and, at the same time, have the energy to parent and engage with a young child, which is so challenging. And I oftentimes suffer from parental guilt because I just don’t have the degree of energy that he needs to engage with him regularly. And so sometimes I do feel bad because I can’t play with him all the time and play as rough as he would like to or do the things that he wants to do all the time. It’s all got to be sort of managed and be like okay, I’m going to need a little break. First let me take a five-minute nap, and then we’ll come back and do something. 

0:05:14 – LAURA STASSI
Yeah, and you talked about your community that created this online comedy, but what about community as far as mothers and children? Have you been able to find your spot? 

0:05:26 – PRIYA
Finding the tribe, or finding the village, is also really hard, particularly here in the Bay Area, because we’re so spread out. So finding help is not easy. You’ve got to have like five different babysitters because at any time one may not work out. You’ve got to find these channels to find help. So you’re always looking for a mom’s group or a babysitting group or some sort of platform where you can find that help. 

I have some comedian friends who are also single moms and middle-aged single moms, so they understand the struggle. And sometimes they’ll help me out and sometimes I can take my son to gigs and sometimes, I can’t. So it’s always a challenge trying to find reliable help, trying to find help that’s going to last for a while. I like to say babysitters expire faster than a gallon of milk. 

0:06:17 – LAURA STASSI
Yeah, and it’s funny because I happen to know somebody who’s 56 or 57, so she’s a little bit older than you are, but she has a 7-year-old grandson. There sometimes is not a huge difference between our children and our grandchildren’s ages.

That’s true. That’s true. 

But you are interested in dating?

0:06:34 – PRIYA
I am interested in dating. I haven’t had a serious relationship since my son was born. But as my son gets older, and particularly as he’s in these age where he’s curious and he’s going to have questions and he’s starting to understand the world around him, I find it pretty hard to date. I say that I just really need a boyfriend between 9 pm and 11 pm only. Really, that’s all the time I have. So it’s hard for me because I don’t feel comfortable bringing someone around. He doesn’t quite understand that Mommy has mommy time and then there’s Jaden time. He thinks anybody that comes over is going to be there to play with him and to engage with him. 

Not a lot of men feel comfortable with that. It’s very hard to find a man who’s grounded and would be willing to take on my situation or be part of it and understand that I’m not looking for a baby daddy, I’m looking for companionship, just like anyone else. But my situation is this. I’m a solo parent, I don’t have someone that I can switch off weekends with, or I don’t have a grandparent that he could spend a night with or something like that. So I’ve kind of just stopped dating because online dating is a lot of work, and I work enough. 

I’m open to it, and I definitely would like to have someone in my life, and I know it would be important for my son to see that his mom can have healthy relationships with adults too. But you do get nervous because I don’t want anything to traumatize him and for him to have any trauma or to see someone that would not be respectful to his mom or treat his mom well, and I don’t want him to consider that normal male behavior. So I’m cautious, very cautious. 

0:08:26 – LAURA STASSI
And understandably so. In fact, I was going to ask you if you do take special precautions. 

0:08:31 – PRIYA
So definitely like first dates, I’m always going to get a sitter. And we’ll meet somewhere public and have a coffee or in a park or lunch or something where I can sit down and sort of feel the vibe, get to know the person a little bit and suss them out a little bit. 

I might do that for the first few dates. Generally, it doesn’t make it past a second date for me, I don’t know why. So I haven’t had to worry about it too much. But after a few dates, if I feel comfortable with that person and I feel like we’ve been able to open up and share some intimacy, to feel a connection, I would want them to meet my son because I just think the earlier you establish that, the better it is and it’s going to just make it easier. 

I tend to gravitate a little bit more to younger men because I feel like they’re upbeat, they’re energetic, they let things kind of roll off their back a little bit more than someone my age or someone that’s older. They’re a bit more set in their ways and maybe not as open. 

0:09:27 – LAURA STASSI
Yeah. Now I’m thinking about just going through partnering with somebody who has a child that hasn’t gone through puberty yet or learned how to drive.


I mean, those are kind of — how do I say this? I mean, they’re beautiful milestones, but they’re also very, very stressful for everybody involved. And so I can see where it might be difficult for somebody to be open-minded enough to want to take that leap again. 

0:09:56 – PRIYA
Absolutely, and I understand that. I met two interesting men in my dating career since my son was born that I thought had the possibility of going further, and they were both online, which was interesting because I haven’t been really able to connect with most people online. I met one guy who was also Canadian and my age and had a daughter my son’s age. 

Oh wow. 

He was like — we came from the same town in Ontario, and we shared a lot of similar interests and so forth, and his second wife was much younger than him too. So it was sort of a similar story, a similar life experience, and I thought, wow, this is perfect. We kind of did that on and off for about two years, and he just wasn’t really willing to take it any further or make much effort to get any further. We did have a few times when our kids would get together, but his daughter was going through her developmental issues, my son was going through his developmental issues. And it just didn’t mesh. 

And then I met another guy online who was very funny, charming, also my age, had an older son who was already a preteen. But we had so much in common, just talking — we would talk for hours on the phone, and it was great. And then we had one date, and it was perfect, and it was a lot of chemistry and exciting and fun; and we talked. And then we had scheduled a second date, and he was going to come to my place because I just couldn’t get a sitter. So he was going to come to my house after my son went to bed, and then he just didn’t show. I texted him to confirm, didn’t respond, and then the next day he texted me and he said, I’m sorry I didn’t respond, but I don’t feel comfortable. I like you, but I’m not sure this is going to work. And so then he just cut it off. 

0:11:39 – LAURA STASSI
Is it because of your son, do you think? 

0:11:42 – PRIYA
I think so. I think it was part of that. I think he might have wanted to become physical more sooner than I would have wanted to, you know. I mean, there was definitely a lot of chemistry between us. 

I try to be more cautious with that and establish more of an emotional connection before I get into bed with someone. And you know, I think he had been married for 20-plus years and hadn’t dated much either. I think there was a lot of things he was scared about that probably he wasn’t sure he was going to be ready to take on again. So, yeah, it was unfortunate because we really got along. And since then, I haven’t really made much of an effort because, again, I’m not someone who’s good at the online dating stuff. You know, I like to have face to face, I like to feel the connection, I like to see people’s body language. I make a much better impression in person than I do online. 

0:12:40 – LAURA STASSI
Priya’s son turned 9 in October. She says she’s grateful she’s had the opportunity to become a mom, and she thinks it worked out better this way. When she was younger and unencumbered, she was able to travel the world. Now Priya doesn’t feel like she missed out on anything.

Priya is still struggling with the dating scene. She says it’s hard to date a man when you’re trying to raise one. Funny — but no joke. 

So far, what I’m finding is no, they don’t. Men and women were both saying, I don’t want to date somebody with a young child. I’ve already raised my children. I don’t want to do that again. 

0:13:17 – LAURA STASSI
That’s Professor Lauren Harris. After the break, she’s sharing some uncomfortable findings not only about dating with children, but also dating with grandchildren. That’s next.



I’ve been told that being a grandparent is perhaps the most joyous experience ever. I’m really looking forward to it. I never dreamed it might interfere with my romantic life, but according to my next guest, it might. 

My name is Lauren Harris. I am an assistant professor in human development and family studies at the University of New Hampshire. I have a Ph.D. in sociology from the University of Pennsylvania and broadly, I look at family formation: how people meet, date, flirt, get engaged, all of the fun stuff, all of the early stuff of relationships. 

0:14:09 – LAURA STASSI
I’m curious about how you got interested in relationships, especially with people as they age. 

It was a very odd happenstance sort of situation. The library system of Philadelphia does a lecture series every summer. One summer they were doing love and romance. It kind of ended up on my desk. They said, can you come in and give a lecture? I said, sure. One thing led to another. I said, hey, I can do something on online dating, I guess. They were like, yeah, sure. I came in. This is the senior center lecture, it’s all older adults. I went in thinking, no one’s coming to this lecture, nobody cares, it was packed, it was busy. 

Older adults were really curious. There was a portion that wanted to know what online dating was like because their adult children were doing it. They wanted to understand what their children were doing, what their friends were doing. But the majority of them wanted to know for themselves. I was very surprised, and I was talking to one of my advisors about it and he was like Lauren, this is your dissertation. So I dug into the literature to see what we already knew about older adults and dating, and we didn’t know anything. There was very little work done, and the majority of the work that was done was mid-eighties and focused on widows. We basically don’t know anything about older-adult dating, and I just thought, this is such an open field. I got very curious about it, and it has been easily the best decision I’ve ever made. 

0:15:33 – LAURA STASSI
So I want to talk about the study that originally caught my eye. 

Yes, the study is called “Older Adults on the Dating Market: the Role of Family Caregiving Responsibilities.” It stems out of my dissertation research. I interviewed a hundred men and women, single older adults in their 60s and 70s, about what it was for them to be single, decide to date, repartner, what dates looked like for them, and the whole gamut. So I sat down with many, many older adults, men and women, to investigate what this process looked like for them.

And so one of the things that they came up with — surprisingly, I didn’t foresee this — one of the things that they mentioned over and over and over again was the role of caregiving in the dating process. And so men and women both realized that the care that they gave their families and the care that their partners, their dating partners, gave their families impacted what they were looking for in a relationship, what they were looking for a partner, and their opportunities on the dating market. And so one of the big differences here was that men and women experienced these things very differently. So when women had caregiving responsibilities — and by that, I mean, maybe they were looking out for an aging parent, maybe an adult child had moved back in with them, or they were supporting them in that kind of way; maybe they were babysitting one day a week, a couple days a week, whatever that might be. When they were caring for their family members, they had fewer opportunities on the dating market. 

Men were not interested in dating women who had caregiving responsibilities, who looked out for their family, who had something on their calendar — you know, every Tuesday and Thursday I have to pick up my grandson from school. They didn’t want to date those women. They saw those women as being too busy, not available for spontaneous weekend trips. They thought that that family member would come in between them and their relationship. So a lot of men talked about well, you know, if you have an adult child living at home, are we going to have overnight dates? Are we going to have sleepovers? Is this child okay with you dating? Are we getting into an argument? 

A couple of men talked about the borderline physical fights that they had had with the woman’s adult children, which was surprising. I know, you’re making this face. 

How old are we?

I know, I know, I know. 

0:17:44 – LAURA STASSI
Just goes to show you, maturity is not connected to age. 

It really isn’t. I know we have this idea that we mature as we age. There’s caveats, there’s — it’s not a linear relationship at all. Yeah, basically I found that men didn’t want to date women who have caregiving responsibilities, and this was both hypothetical and in reality. So men would say oh, she said on her dating profile that she spends a lot of time with her family. I don’t know if I’m interested in that. One man kept saying over and over again I don’t want to date super mom, I don’t want to date super grandmom, I want a woman who’s going to put me first. And that was sort of the sentiment of a lot of men. They saw family and family caregiving as a woman’s priority, which meant they would not be the priority, and that’s not what they wanted in a romantic relationship. 

0:18:33 – LAURA STASSI
Okay, so, wow, yeah. So I have to say from my anecdotal evidence, I hear a lot of women say, I want to be with someone who, because I know he’s going to understand my family, because he has his own family.


But the men were men saying this, even if they had kids of their own? 

Yes, one of my favorites — a man talked about how he was dating a woman, and her adult daughter moved back in with her. And that was sort of a relationship killer for him because that meant — he assumed that meant there would be no more overnight dates. He kept saying, who’s house are we going to? You know? Now we have nowhere to go. His adult daughter had lived with him the whole time. It was never an issue for him that his daughter lived at home with him. It only became an issue when his partner’s daughter moved in with her. And so I think he felt like, oh, we spent all this time at your house, it was fine, but now we can’t do that. We have nowhere to go. So now this relationship isn’t going to work so much. 

0:19:28 – LAURA STASSI
Wow. So now I know this was, you know, 100 people. Is that a statistically significant number? And also, you recruited them from dating sites. 

That’s a very important caveat to this. So I interviewed people who I recruited from online dating sites. If we look at people who are only looking for partners in real life — through friends, activities — we might see something different. So maybe people who are looking for partners through family members, through friends, through organizations, they might be more open to somebody who has those responsibilities. As of what I saw, that wasn’t the case. It came up for a lot of men. So my work is qualitative, it’s interview-based, so we don’t necessarily do statistical significance in this type of work. 

But it came up frequently enough that it stood out. It was not something I was looking for and just came up through the interview. So in that sense, the respondents decided that for themselves, that it was important to them actually. So one of the things that you pointed out was that women have said, I want someone who’s family-oriented, and that’s where it stops. So women will say, I want somebody who’s really close with their adult children. They have grandchildren, they want to do those things, they support them, they’re involved — but not men who have young children. And so men and women are both saying, I’ve raised my children, I’m not interested in doing that again. I want to spend the weekends away, I want to do things, I want to go out, I want to be spontaneous. I’m not interested in helping somebody with their algebra homework. 

I had a couple women who are somewhat similar positions, where they had children around 40, say, and so 45, I know I think one woman adopted a couple children in her mid-40s and so now, they’re 65 with teenagers. And one woman was telling me the story about being on a date with a man and one of her children called. And she said you know, she never calls, I just need to make sure she’s okay and then, you know, I’ll come right back. And he was like no, this isn’t for me, like you need to cut the cord, you need to move on. They’re adults. 

And she was like, I’m a single mother, I’m their only parent. They’re 22, they’re not done yet. I just have a little bit more work to do. And he was like, this is a deal breaker, I can’t do this. And so she was telling me, you know, how disappointed she was, that it’s hard for her to find a partner when she has children in their 20s. One of the things that was coming through in men’s stories was that they see their parenthood as sort of done at 18, done at 22. Like, they’re not children, I’m done, my role is over. And for women, it’s a lifelong role, and we’ve seen that in prior research as well. And so men and women see parenthood differently, and so they’re treating it differently on the dating market. 

0:21:55 – LAURA STASSI
Lauren Harris is currently working on a study about the role finances play in gray relationships. I’ll be sure and report back on her findings. As for this study, as Lauren noted, there are always exceptions. Case in point: I talked to a man who’s been dating a woman for almost a year. A couple of months ago, they flew from the Midwest to Boston to take care of her 2-year-old granddaughter for nine days. I love it.

Still. Maybe Lauren’s research is as good a reason as any to drop the old-fashioned grandma and grandpa honorifics and come up with more forward-sounding names. Like, Gigi and Mimi. I already know I want to be called Lollo. Or how about Beatle Paul McCartney? To his children’s children, Paul is Grand-dude. 

Dating While Gray’s audio production and mix is by Steve Lack: Audio. For more on the show, check out datingwhilegray.com. That’s where you can find the latest episodes, plus the archive of previous episodes. You can also find links to send me questions, comments, tips and true stories through email and voicemail. You know I love hearing from you. While you’re there, sign up for the free Dating While Gray e-newsletter, delivered every Friday to your inbox. That’s datingwhilegray.com. Laura Stassi. Thanks for listening. 

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