I Never Wanted Kids But I’m Falling For A Woman With A Child and Rethinking Everything. Help!

I’m a 38-year old, single male, never been married and have had a handful of serious long-term relationships (2 years being the longest), a lot of short term-dating and over 100 dates that didn’t go beyond a first date. I have been on a dating website on and off for almost 11 years, probably a total of 7. Point being, I haven’t had the most success with online dating or blind dates that friends have tried to set me up on. Recently I met a girl who I have been dating for almost 2 months and she is wonderful. She is down to earth, funny, smart, ambitious, independent, kind and extremely attractive and I mean very, very, very gorgeous.

Our chemistry is off the charts but my favorite part about her is being able to relax and enjoy the moment because as serious as she is about the direction of her professional life, she is able to appreciate the simple moments and humor in life. We haven’t had the exclusive talk yet. Although since I began seeing her, I haven’t been using any of the dating websites I have been on and I am not interested in dating more women to explore my options. Which I am sure says a lot about how I feel for this woman and the direction I am looking to go with her. Also, I will not neglect to mention that she is 23 years old and that isn’t even the issue. I was reluctant and skeptical at first but as I get to know her more, the age isn’t even anything I think about.

The issue here is her child. She has a 3 1/2 year old son. I have made the conscious decision of not dating anybody with any children because I don’t want to deal with the other parent or become part of that responsibility. I understand how much of an asshole that makes me sound like, but after meeting this woman, I am so torn. More specifically, my question is should I give up on this woman because she has a kid? A hard rule I had but now am questioning for this one woman. I have been on dates with other women before who have had children and I chose not to continue to pursue any of them. The thing is, the other women also lacked qualities I was looking for or the chemistry was never strong to begin with. So here I am. I finally found a great girl that I am very much falling for, am sometimes catching myself thinking about the future with her, but now I’m re-evaluating everything all because of her kid. Am I pulling what you refer to (and sorry if I mess this up) as a “blackjack 20”? P.S. She and her ex have 50/50 custody and are very civilized and get along just fine. Thanks in advance!

Ready for Lasting Love?
Ready for Lasting Love?


I rarely take questions from guys, but I thought this was a curious role-reversal.

Put a woman’s name after this question and you wouldn’t be able to tell the difference (apart from the “very, very, very gorgeous” line).   So, Tim, you’re gonna get the same annoying logical treatment that all of our female readers get. Sorry about that, but, well, that’s what you get for submitting a question here.

You’re in fantasyland. This isn’t even your girlfriend yet. She is hope, fantasy, projection and potential.

Let’s begin with what’s wrong with this situation:


  1. You’re 15 years older than she is. That’s a half-generation. You’re close to my age. She was born in 1991. You’ve been an adult since she was 6. So let’s make something clear: she is not your peer. This is not to say that your relationship is “wrong” or “gross” or “impossible,” but rather that it faces its own set of obstacles given how much life experience and wisdom you’ve incurred as an adult, and how little she’s had as a 23-year-old. Put it this way: if I were single again, I wouldn’t even talk to anybody under the age of 34. She may be cute, she may be smart, she may have great potential — but she’s not going to be my peer. You know that brains are still developing until you’re 25 — and until then, you’re more prone to emotional, poorly thought-out, short-term decision making? That’s how she ended up with a kid at age 19.
  2. You’re in fantasyland. This isn’t even your girlfriend yet. She is hope, fantasy, projection and potential. You are thinking about her as your future wife because you’re excited about her, not because this is a real relationship yet. You are in the attraction phase of your relationship right now. Enjoy it. Because it does not last forever. In general, it lasts for 18-36 months. Call me then and let me know if you feel the same exact way about her. Not to be cynical, but I’d be shocked if you did.
  3. Did I mention that she’s not even your girlfriend yet? Oh, I did? I should probably mention that again. I’m sure she’s spectacular, Tim, but you’re putting the cart way before the horse. Statistically speaking — not based on you as an individual — the odds that she’s your girlfriend by the end of the year are low. For you to worry about her being a single mom is nothing if not premature. You have 2-3 years to worry about whether you want to take things to the next level. That’s what dating is for. To figure out if you both have what it takes in the long run.

I know, I know, I haven’t even answered your question yet. That’s because I was sort of saving the kicker for the end:

  1. How do you know that she’s going to want to marry you? You’re 38 and your friends are mostly married. You’re ready to settle down. Are you sure that this 23-year-old WANTS you as her boyfriend, much less her husband, much less the stepfather to her son? Are you sure she doesn’t want to get an education, focus on her job and her independence, play the field for a few years, and then focus on marriage in her 30’s? Obviously, I’m just speculating here, but your question is predicated on the fact that it’s all up to you whether you assume the role of stepfather.

Just enjoy your relationship, get her to commit to you, and see where things go organically.

What I hope I’ve pointed out is that this isn’t entirely your decision, and it’s literally the last thing you should worry about right now. How about you just enjoy your relationship, get her to commit to you, and see where things go organically. Sooner or later, you’ll discover if you’re truly compatible in the long-term — or if, as I suspect, you’re just infatuated with the hot single mom in the short-term.