A Guide to Dating Single Moms (From Someone Who’s Dated Quite a Few)

There are two under-the-radar comedies that are off-season now, but worth the binge as we await their return: Showtime’s SMILF and FX’s Better Things. Both shows have very similar conceits: women hilariously navigate work, dating, family while also raising children alone. They also share DNA in that they’re both semiautobiographical accounts of their stars – Better Things’ Pamela Adlon and SMILF’s Frankie Shaw – who are both working non-A-list actors; each show depicts them enduring the audition process for shitty roles that’ll help keep the lights on.

The elements involving the main characters navigating the dating world resonate with me on a personal level, as I’ve dated more than a dozen single mothers since I was in my mid-20s. I’m sure that people might look at my track record and assume that I’m out here with a fetish sniffing out women with offspring like a truffle pig.

Not the case. I’m not consciously seeking the myriad challenges that come with dating someone with one or several major sentient responsibilities that aren’t a pet. Perhaps they’re attracted to me because they can sense that I have the constitution of a man who was raised, in part, by a single mother. I suppose whatever degree of patience and empathy that’s necessary to enter into a relationship with a single mother is intrinsic to me.

Like many people, I’ve always been attracted to the idea of starting a family with someone who never had a child from a previous relationship, but I got divorced before that could happen. However, being that I’m in my late 30s and typically date women close to my age, I recognize that most of us carry with us baggage from a life well lived. It’s harder to be as picky about dating childless, never-married people than it is when you’re in your 20s…and why be picky about it anyway?

Truth is, I’ve dated some fantastic single moms whose children didn’t deter me from considering a potential long-term relationship with them. I wouldn’t suggest a grown-ass man pass up a potential partner just because she’s already a mother, but there are a few suggestions I’d offer in terms of dating them if you never have – and even if you have but you just don’t know what the fuck you’re doing.

Don’t bitch about canceled dates: Think about what you have to do to get out of the house for a date: Brush your teeth. Apply deodorant. Put on a shirt that doesn’t smell like you threw it on right after leaving the gym. Toss a few sprinkles of water on your balls in case you have a shot at getting your bean wet. Done. Now think about what a mom has to do: on top of all the additional shit society requires of her to look cute for your hapless ass, she has to secure a babysitter, probably get the child fed and ready for said babysitter and wait for them to arrive.

Any of those moving parts can collapse at any time. If that happens and she has to cancel the date for whatever reason, charge it to the game and get over it. She will feel terrible about it, but don’t you make her feel terrible about it. In fact, if you play it well and extend the proper empathy, you’ll earn all the brownie points in the world for the rescheduled date.

They don’t suffer fools as gladly: The beauty of being child-free is that you can fool around with any ol’ poop-butt idiot knowing that they’re your burden alone to shoulder. But many, if not most, single mothers have to consider the additional implications of dating a man who will someday be introduced to their child. Of course, any woman you date with an eye on building a family will size you up as a potential dad, but there’s a difference when that child is already in existence and she can concretely determine whom she does and doesn’t want around them.

So, if you get cut from contention because you bring all the fantastic qualities except that of a good dad, embrace that and think about what it means for you going forward. If you’re nowhere near wanting to be a father to your own child or someone else’s, that’s totally okay, but she’ll pick up on that quickly.

You can’t do anything about the baby-daddy: Unless your lady is the living reincarnation of the Virgin Mary, assume that her child has a father somewhere and that you’ll have to deal with him at some point if the relationship becomes serious. Single dads exist in a wide spectrum – from the doting, involved father who is also open-minded and happy to have another positive man in their child’s life (read: unicorn) to the father whose name you’ll never hear uttered because he literally may as well have just been a sperm donor. (My personal favorite: the mom who told me that her daughters’ father was getting out of jail within weeks.)

You’re more likely to get someone closer to the middle of that spectrum, but assume that you will have to bend to at least a couple of his whims if you plan on being around his children. Of course, your woman’s relationship with her ex – along with any court-established edicts – will play a significant role in the whole dynamic, as well as any headaches it may cause.

Speaking of baby-daddies:

Don’t lean into the disciplinarian role: I’ve had several step-parents in my day, and I’ve encountered a handful of boyfriends and girlfriends from both of my parents, so I know about discipline done terribly. And it’s remarkably fucking easy to do it terribly.

Unfortunately, you might wind up in a weird catch-22 at times where you’re expected to dad it up even though you’re not really the dad. For example, you won’t have as much leverage over the disciplinary methods used on the child, which is like entering a foot race with a sliced Achilles tendon, especially if you’re dealing with some challenging-ass kids who could benefit from an occasional elbow to the temple.

Obviously, there are levels to this shit: if you’ve married her and you’re all one big happy family, you’ll likely have more capital to exert your brand of discipline. But there might always be some degree of a disconnect there if little Tyrone Jr. didn’t hail directly from your nuts. So, if you like her but really loathe her kids, you have a decision to make. Just make sure that decision doesn’t have you in handcuffs and on the 6 o’clock news.

Moms like to wild out, just like you: Even though the Bad Moms films comically disabused us of the notion, I still think a lot of guys view single mothers like a cross between pre-school teachers and fine china: their sensibilities have completely changed now that they have a crumbsnatcher to look out for, and they’re eternally destined to a future of ankle-length floral print dresses and whisper-spelling curse words.

If anything, single moms have more of an incentive to get out, drink and misbehave than those of us who take it for granted. And there’s often a correlation between the age of the child and desire to wild the fuck out – the smaller the kid, the bigger the glass of wine required. Also, keep in mind that while moms are more selective in picking a partner, they might just be using you for your penis and cuddle skills for the moment. Which, of course, we’ve been doing with women since time immemorial.

Fuck your ego: It’s imperative that you understand – and make peace with – the fact that you’ll always be a distant second as a romantic interest, regardless of how much she likes you. The kid will grow and require less of her attention, freeing up more for you. But if she has really young children and you like her, humble yourself and dig in, because a happy single mother will absolutely spread her happiness your way. If you’re worth it.

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  1. Dana February 16, 2018

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