Life Is Messy

Would Dating A School Dad Be A Terrible Idea And Should I Do It Anyway?

Advice for navigating a potential romance with the taboo drop-off dad.

Originally Published: 
Sex & The Single Mom

I recently matched with someone on Bumble that was familiar to me but I couldn’t place exactly how/why until I saw him at school pick-up a few days later and realized he was a parent at my kids’ school. I immediately messaged him to let him know I wasn’t comfortable dating someone whose kids went to school with my kids. He didn’t see what the big deal was, which made me wonder if I was just overreacting. Was I?

Sidebar: I unmatched him pretty swiftly after our conversation and while I almost never saw him before this happened, I see him constantly now. So if my fear was that school functions would become awkward, I made that happen anyway!

I might as well have just gone out with him! Why is dating so hard and weird when you have kids. I hate it!

Dating is hard and weird when you have kids and also it’s hard and weird when you don’t have kids. Dating is hard and weird, and it doesn’t ever get less hard and weird. So I guess we should maybe just start with that.

When you choose to date, you are essentially setting yourself up to have awkward moments in perpetuity. Especially if you’ve lived in the same place for a long period of time. (I recently ran into someone with whom I used to make very questionable choices at a child’s event and had to pretend like the last time I saw him I wasn’t half-naked in the bathroom of Three of Clubs in 2003.) This is the nature of having dated in the same place where you’re raising children, so rest assured that what you are describing is on some level unavoidable.

We are all running into former lovers at the proverbial Stop-n-Drop.

And to your point, this is especially true when you’re dating people who also have kids in the same geographical location. Multiply that by a hundred if/when you live in a small town. And multiply it again if you are dating people with similarly aged kids.

At some point, one must lean into the mess of it all.

But even if you do live in a major metropolitan area, social media combined with Covid-era online sociability has made everywhere feel like a small town. Once my kids reached middle school, they somehow knew every teenager in the greater Los Angeles area. Like, every single one. If they didn’t know the children of the person I was currently seeing, their friends did. Or they followed each other on social media. Or their burner account followed the burner account of an older sister who read something I wrote once and DMed me about it. We are all of us very much connected.

Years ago, I went on a date with someone I knew instantly wasn’t a fit, and after not responding to his texts (I swear I was going to eventually), I ran into him in the lobby of my kids’ school because we were both picking our kids up at the same time for doctors’ appointments. I was not aware that our children attended the same school, and I immediately tried to hide via cave-person instinct. But it was too late. There we both were, standing awkwardly in silence waiting for our children. (That was the last time I ever ghosted someone. Learned a very valuable lesson that day!)

Neither of us knew our kids went to school together and because this was very early on in my time as a single parent, I didn’t want my son to feel uncomfortable so I blatantly lied to my kid’s face and told him the guy was an old friend. I have also matched with people on apps only to realize later that one of my kid(s) was friends with their kid(s) and then immediately unmatched because life is weird enough when you’re a teenager and I do not wish to make it weirder.

All of this is to say that I wholeheartedly understand why you don’t want to shit where you eat. Unfortunately, for many of us, we only have one bathroom and it’s very close to the kitchen.

At some point, one must lean into the mess of it all because, like you said, even when you’re avoiding a potential mess, you can’t really avoid a potential mess. I also think it can be really bonding to date someone who has kids the same age as yours.

And while your comfort is paramount, and I absolutely believe in boundaries when it comes to who we choose to date and how that relationship may or may not affect our children, families, and comfort at school functions, I also think it’s so rare to hit it off with someone and that closing yourself off to potential connection out of fear of awkwardness means there will always be a reason to disconnect.

As long as you’re not throwing the boyfriend out with the bathwater, because you never know unless you’re willing to get to know. You know?

I want to answer any and all questions you all have about the exhilarating, terrifying, and wonderful experience of dating and having sex with new people after becoming a parent. Send me your questions at

Rebecca Woolf writes Romper’s Sex & the Single Mom series. She has worked as a writer for more than two decades and is the author of two books, Rockabye: From Wild to Child and All of This: A Memoir of Death and Desire. You can subscribe to her newsletter, The Braid, for more. She lives in Los Angeles with her four children.

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