The Dating Nerd is a shadowy figure whose whereabouts and identifying details remain unknown. What we do know is that he is really, really good at dating. He’s been on more dates than you can shake a lengthy bar tab at, and he’s here to help the average guy step his dating game up a notch — or several.
Hi Dating Nerd,
So I have a bit of an interesting dating dilemma. I'm hoping you can maybe help me out with it, since you're such a genius when it comes to this stuff (so you say). I recently met a woman online who checks all my boxes. Gorgeous, beautiful long dark hair, funny, flirtatious, and not shy about sending me naughty pictures. Clearly into me but not coming on too strong. We met up for a first date and the chemistry was absolutely there. Hell, I had to stop myself from proposing on the spot. (Or at least proposing we hook up in the café washroom.) But there's just one issue here — she's a mom. That's right, a MILF. She's not a lot older than me, but she had a kid a few years back. The dad is (so she says) out of the picture, and she's not necessarily looking for a replacement. But if I start dating her, am I going to be way out of my depth? I'm not looking to be a dad, or a husband, or any of that stuff. Not that I would never want to be, but that's part of my five-year plan, not my schedule for next week, you know?. But on the other hand… damn, I can't stop thinking about her. And maybe it would be fun to act like a grownup for a hot minute. Should I take the plunge anyway and make sweet body music with this woman?
– Mommy Issues
Hi Mommy Issues,
Should you take the plunge? Probably not. Especially not if you’re asking me this question. Because that means you’re not 100% sure. You need some guy on the Internet to inform your decision. While I’m flattered that you’ve sought my tremendously wise, foolproof dating advice, this is one of those situations where you need to be 100% thrilled about this woman, so much that you’re prepared to ignore whatever nonsense comes along with dating somebody with a kid. Which is a lot of nonsense. If your attitude isn’t, "Hell yeah, let’s jump out of this airplane," then you’re not ready to take the jump. Don’t believe me? Well, let’s take a second to consider the beautiful paradise that is dating a single mom.
Are you ready for the baby vomit? I’m talking about the day when you’ve made a reservation for a Michelin starred restaurant and her baby just starts up-chucking all over everything. Maybe it’s even Valentine’s Day and you bought flowers, and you wore your precious Armani suit. And that’s when E. Coli decides to strike. So she can’t go out. Moreover, since you’re an absolute saint, just a solid dude, you offer to help. So now you’re cleaning up juvenile puke, and getting some of it on your favorite Oxford shirt. Does this sound like a fun time? Do you want to live in a bad Judd Apatow movie?
Then there’s situation No. 2: her ex. Sure, she’s separated from the dad, so her ex should, theoretically, be pleased that there’s some other guy who can be there for her. But that’s the best-case scenario. The worst-case possibility is that he gets jealous when he witnesses your relationship, and tries to get back in there. Or he just doesn’t like you, and he spends all of his time telling your new girlfriend that you’re a garbage human.
And he’s not the only one who might not like you. Have you thought about the possibility that maybe you won’t win the kid over? It's easy to forget this fact, but children are people, with their own stupid opinions — and chances are, the kid misses dad, at least a little bit, and will be highly suspicious that you’re around, stealing mom’s precious attention. You could start dating this woman, establish a wicked sex life, laugh together, have a bunch of fun dates, and then get vetoed by a 4-year-old. A truly humiliating possibility. Remember that you’re entering a relationship with two people in it, at least one of whom is sensitive, volatile, and may be drooling all the time.
OK, you say, no problem. You don’t mind cleaning up baby puke, you’ll go toe to toe with any deadbeat dad, and you’re a real charmer who no juvenile punk could possibly resist. Congratulations on your resilience and charisma, your Amazing Dude badge is in the mail. But there’s something else you should keep in mind. Which is that dating anyone is complicated — even if they’re your ideal match, which you've already make clear in your message, this woman is not exactly.
This sounds like an obvious point, but it’s actually not. See, when we date anyone new, we tend to think of their obvious problems — maybe she’s a rich heiress who’s used to dating men with horses, maybe she’s deaf and you’ll need to learn sign language, maybe she has a kid, maybe she hates ice cream and puppies. What we don’t think about is that these problems exist in addition to the totally normal problems that come with any partner: sexuality is complicated, miscommunications and petty arguments are bound to happen, etcetera. Dating someone with a kid is dating in hard mode. You’ve got to have a tremendous amount of emotional energy or you’re just gonna crash and burn. If you don't — that's fine. There are a ton of online dating sites out there full of gorgeous people who aren't also parents.
Sounds great, you say — you’re good at handling conflict, you’re extremely mature, you’re a relationship expert. Bring it on, you say. Very well, then — proceed with caution, but only after you also think about one more issue.
Do you maybe think you’re confusing what your feelings are here? That maybe you see a problem in this woman’s life, and you want to jump in there and solve it, thereby being A Real Man? Don’t take this question personally. Or lightly. A lot of dudes, myself included, fall for this sometimes. We go for the troubled girl with a coke habit because the idea of turmoil is exciting. We hang out with the depressed girl who’s always tweeting vague, dark poetry because we see her as a problem who can be solved. Lots of dudes love responsibility — the feeling of being someone’s rock, the feeling of coming to someone’s rescue.
It’s really unfortunate that this single mom has to deal with the pressures of both dating and parenting, and that she’s got a void in her life where a good, supportive man should be. And if she’s into you, she’s definitely concluded that you might be the dude who can fill that void. That’s all very compelling and dramatic, and you should be flattered, but remember that this is not your problem. You won’t be any less of a man if you skip this one. And you really shouldn’t get into any relationship so you can fix somebody. Approaching a relationship with that mindset means that you’re dating the perfect woman you see in your mind’s eye, rather than the actual woman in front of you.
Let me fit in a disclaimer at the end here. Single moms are heroes and they deserve a huge level of respect by default. And there is one upside: If she can take care of a baby, she’s probably not a precious, spoiled brat who demands absolute perfection from life, which is an unfortunate state of personality that many young and hot people pass through at some point.
So, you could absolutely have a great relationship on your hands. As long as your definition of a great relationship can expand to include dealing with infant diarrhea, a potentially angry ex-husband, canceled dates, and being judged by a temperamental child. Now that I’ve warned you, all I can do is wish you the best of luck, and say that if you can do all this, you’re a stronger person than I.