I Let My Kids Meet My Girlfriend Too Soon. I Won’t Do It Again.

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There’s a podcast I listen to called One Life, One Chance, hosted by hardcore singer Toby Morse, an explicitly positive person who’s a straight-edge vegan who sees the best in people.

And at the end of every interview, he asks, “do you have any regrets?

Some say yes, and others say no, that the path they’re on is theirs alone, complete with its successes and failures.

I cannot relate to this. Like, at all.

Every single time he asks about regrets, my mind does one of those montages of moments where I die inside, pinpointing my fuckups, leaving me wishing certain things were different, curious what my life would be like had I played situations a little smarter.

I know I can’t change the past, but the past has come collecting its tax more than once. And because of those hard-knock lessons, I’ve learned to think critically and strategically when it comes to being a parent, for better or worse. 

I’m a single dad of two boys.

Me and their mom split during the pandemic, and since then we’ve each had our romantic ups and downs.

While she’s comfortably settled into a new relationship that, from what I can tell, has good bones, I’m a K-Mart Blue Light Special item, complete with damaged box and a cadre of price drop stickers, one a buck cheaper than the next.

After the relationship with my ex-wife ended, me and the streets were simpatico; I refused to be with anyone on a romantic level.

I wasn’t ready and didn’t stay ready for years. I had a lot of ghosts, and there weren’t enough cemeteries to find permanence for the things I had to work through.

Drinking buddies needed only apply, and I was chugging Jameson and taking plenty of spins around the dance floor. (Your boy can cut a rug.) 

But over the summer of last year, something changed.

I’d met a beautiful woman, and I liked her a lot.

Even though it was a cross-country relationship (her in Chicago, me in Austin. Chicago is my hometown, and I visit for a month with the kids every summer.)

We gave it a go.

Logically, we should have left it at “when you’re in Chicago, or I’m in Austin,” but matters of the heart are their own animal. Because she was a COO, she traveled at least once a month, so she made it work that when I was returning to Texas, she’d meet up with me and the kids.

For a few days, we hit the Texas coast. And we had a blast.

She and my boys met and hit it off. We feasted on seafood dinners, splashed on the beach, and goofed around in a perplexing hotel I’d made reservations for at the last minute.

(Think of the experience as indoor camping with bunk beds that reeked of Lysol.) 

She was my first girlfriend post-divorce, and despite only being together for just over a month, it seemed like everything was a good idea – till it wasn’t.

The relationship went south a few months later and the breakup was hard. One thing I didn’t count on was how much my boys liked her, that my oldest asked why we couldn’t FaceTime, or that he got sad when I said he wouldn’t be talking to her anymore.

She was sweet because she sent them small birthday gifts, a gesture that meant a lot to them and me. But it just didn’t work, and that’s ok.

But I didn’t like the sadness in his voice because he’s not used to people coming and going in his life; he’s used to permanence. 

In the wake of that girlfriend, I met someone unexpectedly and fell in love.

Mike Tyson Haymaker hard.

At first, she was leery of even dating a guy with kids, but her best friend convinced her to give me a shot, and in turn, she was my only dance partner.

After learning from the first one; I didn’t want to be one of those dudes that my kids can cite back to being like, “Oh, there was X and X and X and X.” By seeing a parade of women, I didn’t want them to think that relationships weren’t something sacred, which to me, they are.

I didn’t want them to be those guys who are dead inside when it comes to loving someone or even opening up because they’re already marked as the children of divorce. 

The recent ex and I took it tortoise slow on the meeting kids front.

She was one of those children of divorce, and that screwed her up, which she had to work out through therapy.

The idea was always after we hit the six-month mark. But we never hit it. We broke up just before, and it devastated me.

The lessons I learned from that first go-round were true: be judicious of the influence others bring to the table, and be mindful of their imprint on your children because if they bail, there will be questions, there will be explaining, and there will be a sad voice because they remember playing Pokémon together on the couch, not the drama behind the scenes.

The breakup was terrible for me, so I’m thankful they didn’t have to experience the torment, too.

I ain’t letting them turn into one of these fuckbois out there because I didn’t have my shit together emotionally.

Until it’s a confirmed plan to build a life together, they’re not meeting anyone.

Full stop.

I’m not in the streets any longer, I’m on the bench.

I might make Faustian bargains, but I’m not giving my kids the curse of my mistakes haunting the emotional cemeteries they’ll eventually build on their own – for their reasons, not mine. 

Robert Dean is a journalist, raconteur, and enlightened dumbass. His work has been featured in places like Mic, Eater, Fatherly, Yahoo, Austin American-Statesman, Consequence of Sound, Ozy, The Austin Chronicle, USA Today, to name a few. He’s appeared on CNN and NPR. He also serves as features writer for The Cosmic Clash, Culture Clash, and Pepper Magazine. He’s Editor in Chief at Big Laugh Comedy, Texas’ premier comedy production company. He lives in Austin and loves ice cream and koalas. His new essay collection Existential Thirst Trap comes out May 8th.