Dating Advice: How to Handle Babies Big and Small

[This question is a bit on the long side, but a perfect example of hastily embarked upon relationships, dating when you want kids, and a bunch of other nuggets.  Many thanks to the sender.]

Dear David,

I started dating someone about a month ago that I met online. We have a ton in common (he’s presently getting a degree that I also have) and when I met him I found him cuter in person than in his pictures. The first few dates were some serious “Whoa, You!” stuff and we kind of jumped in fast—he asked me to be exclusive very early, which made me uncomfortable but which I agreed to because I liked him so much, and we slept together soon afterward.

We’ve talked generally about some of the important “wants” and he mentioned in passing that he wants to have kids eventually, which made me feel like we were on the same page. For the record: I’m 35, freelance/self employed and still look and live like a younger person, but am getting tired of it. My last serious relationship lasted three years but ended two years ago—the ex and I were definitely on the track to marriage, etc. but got derailed and after a year of couples therapy, I left. This dude is 40 and was in a long relationship/marriage for most of his 20s and 30s. She wanted kids but he didn’t—with her, he says, because he knew the marriage couldn’t sustain it. He’s been divorced/out of the relationship for two years, during which time he sold his house, left his lucrative professional job and basically changed his whole life to enroll in a masters program that he’s serious about. He’s in his first year and making a stipend.

One night we had a date where I hear some things that make my ears perk up. I bring up the topic of whether we’re in the same place given that he was in a longterm committed relationship for so long and may want to sew his oats for a while, whereas I’ve been moving around the country more or less single for a long time and may be ready to settle down a bit more. I mention that I want to have a family and ideally would start within two or three years (again, I’m 35). He basically freaks out and says he “doesn’t know” whether he will be ready to have a family within my time frame, and that he doesn’t want to start down a road that will lead to my disappointment, my leaving him when I’m 38 to find someone who’s ready or staying with him and resenting him. He’s particularly worried about all of this because of guilt from his last relationship where he “ruined someone’s life” by not having kids with her. Continue reading “Dating Advice: How to Handle Babies Big and Small”