Think Introducing Your Boyfriend to Your Parents Is Tough? Try Introducing Him to Your Kids.

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There comes a time in every relationship when it’s reached “that point” and you decide your new boyfriend should meet your parents. This part of the dating process has never scared me; maybe it’s because the guys I’ve dated have been parent-friendly. (I should say there have been plenty of non-parent-friendly guys, but those ones usually don’t make it past a couple of dates and therefore are not even considered for a Meet the Parents dinner.)

This is not to diminish the fact that I was scared my parents would hate my boyfriends, or know deep down that they weren’t right for me, or that I missed the fact that one of these guys was actually a serial killer. (As far as I know, no one I have ever dated has been a serial killer.) When the breakup comes — I’m single now, so of course it came — my parents, or more particularly my mother, is all, I could have told you that it wasn’t going to work out. “Oh, thanks for the heads up, Mom!”

But of course I didn’t want to hear that when I was dating the guy. Who wants to hear that? After the fact, you think that info may have come in handy, but would it have?

Before I get all Carrie Bradshaw, let’s move on.

There’s also another point in all relationships for me: When does my new boyfriend meet my kids? This is a thing single parents have been doing forever, so I’m not breaking ground here or anything — I know that — but I don’t personally know any other single gay parents. Maybe I should try to change that by joining a group or something, but I just haven’t.

I have two boys (ages 6 and 7) with an ex-wife. I was married, came out, and then got divorced. Certainly not a typical path, but again I’m not the first to blaze that trail either. I am, of course, the only person I know personally to have done that as well. My ex-wife and I have joint custody and have worked really hard at staying friends and working together to raise our kids. When it comes to the boys meeting someone I’m dating seriously, she’s the first to know if that’s going to happen. It’s something we talked about early on and have stuck to it.

The first time my boys met one of my boyfriends was at an IHOP over pancakes. My boys and I were going to be spending the afternoon in Harvard Square in Cambridge and I figured this would be a good opportunity for them to meet my then-boyfriend in a neutral, comfortable setting. We got there first; I told them my friend was coming to join us for lunch. This was almost five years ago now, so they were both still really little and the idea of a “boyfriend” was still a concept they didn’t quite grasp. (We did have the talk with them about how some daddies like girls and some daddies like boys and I was one that liked boys — I mean we had a bigger talk, but that’s the basic gist of it.)

When my then-boyfriend arrived I knew he was nervous to meet them, but excited. The boys didn’t really talk much to him. They ate their pancakes and colored on the menus. The first meeting went well as far as I was concerned; at least now they had a face to his name when he came up in conversation.

My older son was, and still is, very interested in all my friends and what I do when I’m not with my boys, as are most kids. After that first meeting, he would ask what X (let’s call my ex-boyfriend, X, for simplicity’s sake, OK?) was doing? Is X coming out with us? When do we get to see X again? My boys spent a few more times with him and even stayed over at his & my apartment when we lived together for a short time.

When I broke up with X (that’s another story) my boys did ask a few times what X was doing. I told them that sometimes people stop being friends for different reasons, but assured them that X still liked them even though we probably won’t see him again. His name eventually stopped coming up, and they moved on.

They haven’t met any of my other boyfriends or people I’ve dated since then. Now that they’re older, I’m more apprehensive. What if they don’t like the guy? What if they like him a lot — then what happens if we break up? They’re not little anymore and will likely not forget this guy as they get older. I want their real first concrete memory of Daddy’s boyfriend to be good.

I’m probably over-thinking this somewhat; I know that kids are resilient. But they’re my kids and as long as I can protect them, I will. Protecting them from what, though? When it comes down to it, it’s really about my insecurity that whatever relationship I’m in won’t be good enough and that it won’t last. I’m single now, but when the time to introduce them to someone new eventually comes, hopefully I’ll be more prepared to face these fears than I’m sure my boys will ever need to be.