05/29/2013 02:25 pm ET Updated Jul 29, 2013

Dating and the Single Mom: When Do You Come clean About Having Kids?

Having kids is often a deal-breaker when dating. That is OK.

When it comes to dating, the possession of offspring is right up there with bisexuality (in men), herpes, smoking, being a Republican, and refusal to perform oral sex. Most people have a few things they just aren't willing to compromise about. No exceptions. As far as I'm concerned, that is perfectly fine.

But that doesn't mean that dating as a single mom can't put you in a pickle. Scratch that. Cruising for men can put you in a pickle.

Consider this weekend when I went out with a few SMILFs. And when I say "out," I mean to a bar where we drank a lot.

We were all having a fine time enjoying our jalapeño margaritas when suddenly a swarm of cute, funny, drunk guys approached. One was celebrating his birthday, most were about our age (mid-30s), and most were firefighters. It was all good fun -- lots of laughs and flirts and drinks all around, even if these dudes were not relationship material. After all, what single mom couldn't use a dose of absurd, slobbering (if innocent) attention from some swaggering members of New York's bravest?

When one tall blond asked us, "You girls must do really well in a place like this," my SMILF friends and I shot knowing looks at one another. After all, if these dudes a) took off their Yuengling goggles they might not call us "girls," and b) were pelted with our full stories of lingering divorce proceedings and preschoolers tucked into bed at their fathers' apartments for overnight visits, gone would be our free beverages and lingering (albeit out-of-focus) glances. Or so we assumed. So we kept our glossed lips closed.

Now, a certain member of our posse caught the attention of one of these gentlemen, and her evening proceeded on a different path than the rest of us. Suffice it to say that his studio apartment was near the bar. After all, had she taken him home, he may have tripped on the Lightening McQueen collection populating the apartment and noted the California Baby wash in the bathroom. Post-coital he may have been surprised that the only snack she could offer was individually wrapped string cheese and a juice box.

That's right: She never told him she had kids.

Turns out, the random drunken hookup turned rather sweet and tender, and now she'd like to see him again. But he doesn't know she's a mom, and she has no idea how to broach the subject -- or when.

"I don't think that mentioning my divorce or kids right off the bat is my best bet," she said later while dissecting her conundrum. "It's pretty much guaranteed to shut the conversation down before it starts. But if I were to bring it up later, I might give him a chance to get to know and like me -- and consider what it might be like to date a single mom."

My first impulse was to smack the shit out of her. What is this -- we manipulate men into loving our sexy ways? Fuck them so they fall in love with us, then drop the information bomb about the most important topic in our lives -- our dear children? Gimme a break! I say, lay it out. Just slip it into the conversation ("Yeah, just wait till you see my double C-section scar! Yikes!"). Let them make an educated decision as to whether to ask for your number, and go to sleep knowing that you are a decent, honest human being.

On the other hand, I've come to realize that I am the ultimate romantic. I believe that the most wonderful things in life are those that we cannot plan for, the things that challenge our ideas about who we are and what we believe. The best experiences in life are those that come with a big dose of magic. And let's face it -- any man willing to sign up for the shitshow that is often single motherhood will have to be rather magical.

I have full faith that there are plenty of guys out there that fit the bill. But to my friend's point, some of them might not know it until they get friendly with some rather magical single moms (and when I say "moms," I really mean me). Meeting someone at work, by frequenting the same schwarma cart, on OKCupid, or through friends is an entirely different dynamic than chatting up guys at a bar. At a bar, it's all silliness and fantasy. Until someone gets laid, of course.

While there lots of men who are open to dating women with children, many -- most, probably -- are not. Lots of factors at play, and in our case, age is paramount. I asked a 54-year-old divorced friend his opinion on the matter, and he was all for full disclosure. But he pointed out that if he met a woman in a bar who was his age, he'd assume she had kids. Professional 35-year-old women hanging out in a New York City bar? Not so much.

As for my friend (and when I say "my friend," I really do mean my friend), she's hoping her love interest Googles her to find the readily available truth about her family status without further effort on her part. So far, he appears to remain clueless. What do you think she should do?

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