Is It Possible to Date While Pregnant?


I’d love to hear your thoughts about dating while pregnant. Here’s my story: I’m divorced, and have two great kids age 9 and 12. I’ve been dating for about 2.5 years, following your advice, understanding that it’s a process, being patient, and learning about myself and about men. I know I will eventually find my great match. Well, I was dating a nice guy for a couple months and it didn’t work out. I found out I was pregnant after we broke it off. We practiced safe sex, and yet here I am. I’m planning on keeping the baby and we have decided to co-parent as friends. After the initial surprise wore off, a lot of self-reflection, and talks with the father, I am happy about it and feel confident that it’s the right decision to proceed the way we are. I am already accustomed to being a single mom, and I always wanted a 3rd child, a dream that I thought I had to give up on when my husband left. I’m 44 and 2 months into the pregnancy and so far, everything is smooth sailing. I don’t want to put off looking for my life partner for two years while I’m pregnant and have an infant. Of course, I realize that my pool of interested bachelors may be limited or different than it was before.

I consider myself to be an all-around great catch, but I am sure this will narrow down my options for a while. I am cute, fun to be with, easy going, positive, in good shape (growing at the moment, but have always done a great job of bouncing back after my previous pregnancies), I own my own business and am economically self-reliant, and am not worried that the new baby will interfere with that.

I’ve got everything going for me and don’t want to stop my search for love, although, I may not be going out as often as I was before simply because I am going to bed earlier and not drinking for now. Even if I don’t find someone until two years from now, I don’t feel like I should banish myself from meeting people and having a nice time getting to know new men during this stage of my life. I’m okay with being alone for the moment, but two more years is a long time to be alone. So, how should I proceed? Do I tell people about this open and honestly? Do I write it in my profile? What are some things I should look out for as I chat with new prospects? I have turned my profiles off for the time being while I think about my approach. Please help!


Dear Jenny,

You’re having a baby out of wedlock with a guy you dated for a couple of months. You’ve decided to keep the child and co-parent, and you’re confident that, as an economically self-reliant woman, the new baby won’t interfere with that.

Fair enough.

You’ve been a parent longer than I have, so it’s not my job to remind you that being a working single mother with a new baby is just about the hardest job there is on the entire planet.

You may be the greatest catch on earth, but who, exactly, is looking to partner up with a woman who is going to be the mother of an infant — a breast-feeding, up-all-night, suck-up-all-the energy, dictate when-you-can-and-can’t-go-out infant?

But that’s your choice and I support your ability to make that choice. I also support the concept that you don’t want to be alone for a long time — that love is important and something worth having immediately. I wouldn’t be a dating coach if I felt otherwise.

Here’s where we seem to part ways:

I’m a reality-based dating coach. I have a hard time indulging people’s fantasies just because they’re technically possible.

Declare your love before you’ve ever met in person? Have sex in the bathroom on your first date? Elope after one month? Sorry, but dating while pregnant is kind of in that realm. Someone may have pulled it off, but there’s a reason you don’t hear many marital success stories that begin this way.

Naturally, I do know a woman who successfully dated while pregnant and met a great guy who wanted to become a father. Lucky her.

Personally, I think pregnant dating would look a lot more like this.

I’m not making fun of you, Jenny. If anything, I have great sympathy for you, as well as admiration for your can-do attitude. What you seem to have barely considered is not simply how YOU feel about this situation but how MEN would feel about dating you at this time.

It doesn’t seem like you’ve factored that into the equation, so let me tell you as honestly as I can: most men wouldn’t be interested. You may be the epitome of the “has-it-all-together” single mom, but it’s not a stretch to say that this is about the last situation a man would want to get himself into.

Your love life should (and will) take a backseat until your youngest is in preschool and you will be a single mom who is a perfect fit for a single dad in a similar situation.

You’re already a working mother of two, presumably with many demands on your time.

You’re now pregnant with a third child, sired by a man you’re no longer dating (who will co-parent).

You may be the greatest catch on earth, but who, exactly, is looking to partner up with a woman who is going to be the mother of an infant — a breast-feeding, up-all-night, suck-up-all-the energy, dictate when-you-can-and-can’t-go-out infant?

That’s not a slam on you. It’s a simple question: who’s your target audience?

      – Not men below 40 who want to have their own kids. They’re looking for women, 25-35.
      – Not men between 40-50 who want to have their own kids. They may consider women up to 40.
      – Not men between 40-50 who have no interest in having more kids. You’ve got one on the way.
      – We could say that maybe men 40-50 who want MORE kids could have potential, but do they really want to get on board with two other fathers and a wife who has to put her baby’s needs first?

Maybe — if he’s really, really desperate to have a family and sees no other options.

So, very much like this blog post where I expressed deep sympathy for the reader but couldn’t easily see a path to success, I wish you the best of luck, but would think your love life should (and will) take a backseat until your youngest is in preschool and you will be a single mom who is a perfect fit for a single dad in a similar situation.

But right now, NOBODY is in a similar situation.

Finally, if I’m wrong, more power to you. I’m rooting for you to get what you want, no matter what.

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  1. 21

    I agree it is going to be really tough to do and it is probably best to focus on giving birth and caring for your child.      In the world of online dating   you are going to have a very tough time unless there are men that have pregnancy fetishes and surely that won’t last long, because well eventually you will not be pregnant.   Online dating is super competitve and while as a non pregnant woman I bet you are quite a catch, and still have a hard time, as a pregnant women most men will simply overlook you.   That’s not right, it just is.   Of course there is the chance that in living your everyday life you may meet someone and decide to date, it happens in Hallmark movies :).      But during this very sensitive time it is likely not a good idea for you or for your child.   I think the best thing to do is tell yourself that if you are going to be alone you are okay with that.   Doing so prevents you from feeling the need to rush to a relationship.      Good luck to you!

  2. 22

    Honestly it is really hard to even consider this question seriously. I mean, could she serendipitously   meet the love of her love while pregnant, say an artisanal cheese vendor  at a farmers market who looks like Alex O’Loughlin 🙂 ? Yeah, sure stranger things have happened. But I wouldn’t count on it, and moreover, I would not put any effort whatsoever into “finding the one” during this phase, beyond just taking care of yourself, staying healthy and active with your usual lifestyle. I wouldn’t go about it proactively, as the return on effort in such situation would really be crappy, IMO. In the OLD she’d be viewed as a freak, you can’t really pull off the bar scene past the 2nd trimester, and how much energy would she have to go out anyway? Doesn’t seem worth it.

  3. 23

    I once dated a woman in similar circumstances. I answered her personal ad. She had a 2 month old at the time. I was interested in pursuing the relationship, but after several dates she realized that taking care of the kid and trying to date were just too much for her, and she ended it.

  4. 24

    I might be totally wrong, but my first intuitive feeling when I read Jenny’s story was – safe sex? I wonder. She admitted she wanted a third baby. She’s not the slightest bit bothered that she and the father are not together any more, she’s got her wish. Now to me, that speaks of her wanting to fill a void inside herself rather than putting the best interests of the child first. People may slam me for saying this – I don’t care. This situation is not ideal for the children, who thrive best in a loving home with both their parents, not different men wandering in and out of their lives. Jenny honestly seems a little selfish to me to be wanting to bring another man into the mix whilst she is going through the ups and downs of pregnancy and caring for an unborn child. She seems very emotionally needy to me. That is tuppence worth on this situation.

  5. 25

    Hey I am an optimistic and if you want to date then go date. I mean you never know unless you try. If you see a chance than go for it. Dont look for someone to tell if its okay. If there is a will there’s is a way. So go ahead make a way and be the exception.


  6. 26

    What concerns me about this letter writer is less about dating while pregnant as there does not seem to be much consideration given to how her actions are going to affect her two young kids and unborn child.   Her kids already have to deal with sharing time between two parents, with a mom who sounds like she works full time and more with her own business. Now they have to adjust with a new sibling who will likely consume most of their mom’s time and energy as the pregnancy goes on and the subsequent months afterwards.   On top of that, they are going to have to share whatever time and energy are left with their moms agenda to date and the emotional ups and downs the mom will have to go through for that??   What exactly are the scraps of time and energy that are going to be left over for these poor kids?   Not to mention it is not a walk in the park to be pregnant at 44.   I’m younger than you, in my second trimester.   I’m fit, had virtually no significant pregnancy symptoms and have an adoring husband who insists on doing everything at home so I can rest after my demanding job.   And I am still exhausted at the end of the day and can barely stand up.   Not to mention I cry now when watching Disney movies.   I cannot imagine going through dating like this – and I am not responsible for any other kids!!   I’m all for finding love, but you made a decision to have these 3 kids. They are your primary responsibility.   Is it so hard to wait a few months before your two kids lose more precious time when the baby comes to just give them your undivided attention?   Are you that desperate to be without a man for such little time?

      1. 26.1.1

        Thank goodness for that, Evan.   Can’t say that I started out particularly wiser or smarter than anyone else but I sure learned a lot from you and the other Focus women! 🙂

  7. 27

    The real threat is men who will use her vulnerable situation for their own advantage.   Be it sex, money, control or all three.   She is living in a fantasy world of delusion.   Finding that perfect guy to accept her situation is 1 in a million, finding a guy who will pretend to the 1 in a million to exploit and use her.   Pretty much 100% guarantee.   I married a women with MS so I know about acceptance.   I think even I would walk away in this situation.

  8. 28

    I am sorry to appear blunt here, but you’ve got to be joking. You’re not living in reality. You already have two children and you’re pregnant with a third. All of those children are going to take up huge amounts of your time, as well as your business.

    The other thing is… You’re asking for cuckoldry. Men are hard-wired to avoid that.

  9. 29

    Is it possible? Sure, anything is possible…but I would gently suggest that Jenny manage her expectations in this situation.

    I can speak from experience on this!! I was 4 months pregnant and out for my sisters birthday when I met a guy who was friends with her boyfriend. We were very attracted to each other & even ended up making out by the end of the night, and continued dating for several months. It was very casual, I never referred to him as my bf. Actually I introduced him as my “dude” just like the guy in the towel on that Seinfeld episode.

    After my daughter was born things sort of fell apart with us, for several reasons, and there was some hurt feelings on both sides. But we both moved on & after several years we are friends (he is still close friends with my brother-in-law)

    I’m happy that I was able to date during my pregnancy but I should add:

    although he was attractive and could be very sweet, he also lived in a trailer with his mom and didn’t have a job or a car

    and I was 28, not 44.

    I approached the situation strictly in terms of dating for the sake of dating, not dating with intention of marriage. If you are looking for your next husband with a bun in the oven that is a tall order.

    But hey, crazier things have happened, and if you can imagine it then it’s still in the realm of possibility. Best of luck!!

  10. 30

    I hate to say it but your babyfather sounds like a good guy-could you not just try and make a go of things with him again? It might not be perfect but if it’s okay and you have a child together would it not be better than ending up alone or with someone not as nice, or who just wants one thing-there are guys with weird pregnancy and lactation fetishes you know

  11. 31

    I agree with Evan. This seems ridiculously unrealistic to me. And I also agree with another poster or two who feel sorry for the children. Nothing more disruptive to a child’s wellbeing than having strangers come and go in their lives. Totally debilitating for them. Creates a lack of ability to trust as well as sets an example for their own future relationship behavior. Not good.

  12. 32

    Why wo.u ld men below 40 be ibterested only in 25/35 yo women? So many couples tjese days with him being actually younger than she is. Evan and.his wofe   himself. And no, this is no longer 1% of   couples. Most couple i know have roughly the same age. This just seems weird.

  13. 33

    I dated while pregnant.

    I was living with this guy, whom I thought I would eventually marry, when I found out he was living kind of a double life (another woman across the country, “business trip” to see her, etc). We broke up and the following week I found out I was pregnant. I was already a divorced single mother (three kids, two of which are disabled and you’d think that would cause problems in my dating life… but only once has it been an issue). I have a good job working from home and decided to go ahead with the pregnancy and have a positive mindset about it.

    I didn’t see any reason to put my life on hold. I dated throughout the pregnancy. I often joked that the father of the baby was dating, so I can too. Haha!

    Many men were interested in me. Now, some just wanted sex due to a pregnancy fetish, but I could sense that right away and discarded those. I went on dates with several nice men and I had a lot of fun. One I liked, but didn’t work out as a boyfriend, for reasons other than the pregnancy, but we’ve been friends for several years now and he’s a big part of my life. There was another who very seriously wanted a relationship, but I unfortunately didn’t feel “that way” about him. And a few other random dates that were fun but inconsequential.

    I met someone during my ninth month and we became friends. We didn’t become intimate at that point, obviously, but he was a sweet younger man who liked children. He had one of his own, but his ex had moved out of state with their baby and he missed her a lot. He was heartbroken but hopeful we could build a relationship as we had a ton in common.

    I had the baby, everything went great, not a single sleepless night, and I breastfed her while working from home each day. I felt fantastic and looked like I’d never been pregnant the day after I gave birth. The new guy and I continued to date, and of course we weren’t “going out” anywhere… He’d come visit me at home and get to know my other kids. He’d hold the baby while I cooked for him. Stuff like that.

    At four weeks postpartum I couldn’t wait any more. I liked him so much and felt so attracted to him, I jumped him on the couch while we were watching a movie. My newborn was sound asleep. I had some of the best sex of my life that night.

    The relationship lasted 15 months, and ended because he died. Yeah, sorry to throw out such a horrible ending. But my memories of him are beautiful. I was in such a sad place, having been left pregnant by a cheater, and there was this sweet, super good looking, intelligent guy waiting for me. I’ll always be grateful that I decided to be brave and keep dating anyway. I have many pictures of him with my daughter. He loved her, and she got to have the experience of a father figure.

    You know what he mentioned admiring about me? The fact that I didn’t opt for abortion, and was willing to sacrifice (possibly) my chance at a personal life to do what I felt was the right thing. Kind of ironic that I was willing to potentially make that sacrifice and ended up not having to.

    If you’re wondering, yes I’ve managed to move on from that tragedy and begin dating yet again. I have four children, two disabled, one a toddler, and a terrible history including losing someone I loved… and I have never had a shortage of men interested in me. So my point is, if you’re in this situation, go for it. You know what you’re capable of, and deserve. No, not all men want to date a pregnant woman or a woman with a baby, and some are indulging a weird fetish (I got some odd messages), but all said and done, YES there are men who WILL want to date you. Good ones, too.

    Good luck!

  14. 34
    April H.

    Why not take this opportunity to make it all about you? Skip dating. Focus on enjoying your pregnancy, getting ready, getting sleep while you can(ha!) and giving your other kids as much attention as you can before a third shows up?

    This isn’t a judgment, it’s an observation. It seems you have your hands full and bringing more people into the mix might…make it messy. Life rarely turns out like a Hollywood film. It’s just not realistic. However, you could “marry yourself” for this time and truly make it special. That…and a few new..ahem…”toys”…and a good foot massager…and you’re all set.

    Being alone is a beautiful thing. So many cannot do it – or they need a partner to validate them. You are in a fortunate position where you have the option to be solo and do things as you please, yet you have others to help with your child(ren).

    Best to you.

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