Family-dating fails: Funny now. Not then.

We all know all about mommy-dating and its perils. When looking for moms and kids to hang out with, it’s hard to find the right chemistry. When you do, though, it’s an awesome combination. Like Oreos and milk. Chocolate and peanut butter. Wine and … well, anything. Wine goes with everything.

But here’s something even tougher: family-dating. Finding a family your whole family likes is like finding a meal that your meat-eating hubby, nugget-loving toddler, and wicked-picky preschooler can and will eat.

Difficult. Bordering on impossible. Seemingly just a pie-in-the-sky dream. Yes, I’m speaking from experience.

I find a family dating fail almost always falls into one of three scenarios:

1) The moms are friends. The kids are friends. The dads have zero in common. One guy loves the Red Sox and the other hasn’t the foggiest who Big Papi is. Or one talks about clients and spreadsheets and stock markets, and the other nods politely while wishing he was at home. With a beer. Far, FAR away from this guy.

Or the worst scenario: the friend’s husband is actually a jerk. Oh, man, does that suck. What’s worse than wondering What the HELL does my friend SEE in this guy? What possessed her to procreate with him?

And in this lovely instance, you sit there during dinner biting your tongue, because you really want to take your dinner plate and crack it over the guy’s head. And throw his third fancy-pants drink THIS HOUR in his face. And your husband is sitting on his hands so he doesn’t sucker-punch the dude. You know. Hypothetically speaking.

2) The dads are friends. The kids get along. The moms couldn’t be more different. This scenario usually rears its ugly head when the men are friends from high school or college and decide to get the families together. Have you run into this? I don’t think it’s too common. Because really, how many guys are actually motivated enough to make plans with their friends? I am the Julie McCoy* of the house. Without me, this ship’s social calendar would suck.

*Love Boat reference. Please tell me you got that? Or am I just old? I am old. Crap.

But … it does happen. And when it does? Painful. Just painful. My advice is to do what I do and hide behind your kids. And make sure your husband is the designated driver.

3) The moms and dads hit it off. But the kids … well, not so much. This is the biggest bummer, I think. You’re so excited that the husbands actually LIKE each other and have things in common. But the kids? They are a disaster.

They fight. And whine. And hit each other with plastic baseball bats. And you spend the whole time refereeing instead of hanging out with the adults. Which turns a fun night with friends into a night just like any other in your house. AND YOU DON’T EVEN GET TO DRINK THE WINE YOU BROUGHT. Not that you’re bitter or anything.

The happy ending to this is … after many family-dating nightmares, we are now in a happy relationship with neighbors of ours. Which is awesome. The kids play. The adults grill and drink. And no one has to drive. SCORE.

But what about you? Is family-dating a disaster for you? Do you have some funny family-dating fails?

Back on the prowl and putting on the moves: Mommy dating

Uncertain glances. Hesitant smiles. Some perfunctory small talk as you feel each other out.

The end goal? A real first date.

Playdate, that is.

It is with some nostalgia, and yes, some nerves, but I am throwing my hat back in the ring. It’s time I got back out there and into the world of mommy dating.

I am actually a seasoned mommy-dater. It took a while, way back when Anne was little, to find the right match.

I frequented the popular singles-bars of mommy dating (playgrounds and libraries), looking for the right connection. After some promising sparks I had a bunch of completely miserable first dates.

But in the end, I did connect with not just one person, but a fabulous group of mom friends. Score!

Our kids were young. We were sleep deprived. And we were all looking for the same thing: real, cool, normal moms to hang out with.

Oh, how I adore these ladies. We vent about our kids, tell our life stories, and have a grand old time together. We get together with kids and without kids. These are real, true, stick-together friends.

But now our kids are older and we all have different schedules. No one’s around on the two mornings a week that Grace is home with me. We still get together, but less often with the kids and more on our own.

I know that two mornings a week with nothing planned will get more than a little boring in the long winter months. Having a friend or two to get together with would be nice.

So I guess it’s official: Grace and I have flipped our social status to “looking for a new relationship.”

But this time, I’m finding the world of mommy dating is even more complex.

The first time around, my kids were young enough that they weren’t choosy about their playmates. It was really about the mom-to-mom connection.

But now? Grace is three. She’s got a personality. And so do I. Which means we’ve moved on to double dating. If it doesn’t work for both of us, it’s just not gonna happen.

And the other shocker: I have been around such real, normal moms for so long – both in real life and online – that I forgot how many moms are still so UNREAL with each other.

And I think – no, I know – that when I’m doing the small-talk thing with these kinds of moms, they’re shocked by how honest I am. Which is fine, because they’re saving me from wasting further get-to-know-you time on them.

For example. Holiday break is over. Back to school, dance classes, and so on. I’m chit chatting with another mom and she asks the perfunctory, “How was your vacation?” question.

My answer?


And the way a mom reacts to that answer tells me whether or not I have any desire to continue speaking to her.

The looks I have received have been telling. One of confusion. One of wide-eyed silence. One of smug judgement. And one of complete and total understanding, accompanied by a conspiratorial laugh.

Guess which mom I spent an hour laughing with during our girls’ dance class?

She’d be a kick-arse mom to hang out with, but her younger kid is boy and they live kind of far from us. Sigh.

Could’ve been so beautiful, could’ve been so right…

Wish us luck at the library next week. I hear it can be a bit of a meat market.






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