Ask A Cool Dad: My Daughter Is Dating Someone Who’s Nearly My Age

Do I have to kill him? Kill myself?

daughter dating someone my age
Mike Falco for InsideHook

This is Ask a Cool Dad, in which our resident dad who is also cool fields questions from readers about how they, too, can navigate the difficulties of parenthood without looking like a square. Have parenting questions of your own? Send them to

Dear Cool Dad,

I am the 51-year-old father of a 22-year-old daughter who recently brought her new boyfriend — a 45-year-old man — home for Thanksgiving. It’s not like there was zero warning — she was always mature for her age, but I guess I just never expected to see it play out with such a significant age gap. I’ve never really been the controlling, overprotective dad type, but I can’t help but feel weird about the fact that my daughter is dating a man who is basically my age. (And, while I hate to bring up the whole “daddy issues” cliché, I can’t help but worry what other people might think it says about our relationship.) My first parental instinct is to put a stop to it, but obviously I know I no longer get a say in who my adult daughter dates, and while I’m admittedly skeptical of any man dating a much younger woman, there doesn’t seem to be anything unsafe or otherwise concerning about this relationship. We had a busy holiday and my daughter and her new boyfriend didn’t stay with us, so I was mostly able to get away with a quick hello and goodbye, but this is the first person my daughter has ever brought home to meet our family and I’d like to make an effort to get to know him when I see him again over Christmas — I just have no idea where to begin. What’s the script here? And how can I overcome the instinctive weird feeling I have about this whole thing? Perplexed Dad

Well, shit. I want to start by saying kudos to you for recognizing that you can’t just demand she stop seeing him, because that would likely not be very productive. She’d just wind up hating you and, even if only out of spite, continuing to do the thing you so desperately want her to stop doing — seeing him — because, frankly, that’s what any awesome take-no-shit young woman like the kind I hope you raised would do. But yeah, I imagine it feels mega weird.

Assuming you have a halfway decent relationship with your daughter, I would suggest being as candid with her as possible about your concerns. Do you feel like she’s being preyed on in any way? Are you worried she’s going to get hurt? It’s important that you allow her to understand where your head is at, while also making sure she doesn’t feel like you’re judging her, or him, even, the slimy old fuck that you believe him to be. There are, after all, objective truths at play here: What she’s doing is unusual. It’s not weird or strange or, god help you, insane. But it is … unusual. Out of the ordinary. Which is enough to warrant a conversation, at least.

Let her know you’re on her side, and that you just want to make sure she’s comfortable with everything that’s happening and that she’s being treated well. If she is, and you remain concerned that she’s going to be ruined in some fundamental way by this experience, well, I hate to say it, but … such is life. You have to let it happen and be confident that she’s capable of handling the fallout, whatever it may be. And remember: it’s entirely possible there will be no fallout whatsoever, that they’re just two people who enjoy each other’s company and are getting from each other what they both need most at this particular point in their lives. Do I think you should spend a lot of time contemplating what those things are, exactly? Nope! I most certainly do not! Not. At. All.

Now, one particularly dicey potential element of this situation — which I will assume is not the case here because A) you didn’t explicitly tell me that it is and B) it doesn’t seem like they’re hiding anything — is whether the dude has a wife or kids or any of that fun stuff. In which case … I don’t know. I guess I would ask her to consider how she might feel if she were to find herself in the situation his wife is being put in? But maybe his wife sucks and is an asshole and also it’s just not your daughter’s problem? I don’t know. You might need to find an even cooler dad to answer that one.

Dear Cool Dad,

I am an uncle to two nephews — ages 4 and 2. It is that time of year when I need to buy them gifts. Traditionally I’ve been the uncle who buys them shit that I think is cool and they probably don’t but hopefully someday will: antique toy cars, weird stuff I find while traveling, the kind of block sets you can only get at specialty toy stores, etc. I’m starting to think that this is dumb and self-serving and I should just get them stuff that lights up and makes noises and generally promotes hooliganism. But I also know that I’m not going to outspend another uncle who can afford bigger, noisier, light-up-ier toys than I can. Help. — Uncle Wally

Dear Uncle Wally,

Before I became a Cool Dad, I, like you, was a Cool Uncle, and I found myself faced with the same conundrum. I had a reputation to maintain, I felt, and that reputation in no way included purchasing plasticky toys from Toys ‘R’ Us or whatever. I remember opting for things like musical instruments, sports jerseys and even “cool” clothes from places I knew my sister would never bother to shop because there is probably nothing dumber than buying expensive clothes for kids who grow faster than the line at Popeye’s when they restock the Chicken Sandwich.

But yeah, one of the things you start to realize once you spend a ton of time around kids is that they really, really love stupid shit that is probably making them dumber. And when you’re a parent, you have basically no choice but to indulge them in at least some of that crap, or you risk them openly resenting you and wondering why Santa cares more about other kids.

So, here’s an alternative. This might be a bit trickier for the 2-year-old, but consider giving them something experiential. Buy them tickets to an event you think they’ll like. Maybe it’s a baseball game, maybe it’s a Broadway play. Maybe a trip to the zoo. Make a whole day of it. Plan a meal, get some ice cream. Find ways to give them a glimpse into your own life that will make them realize how badly they want to be like you. Maybe let them hang around you and your most kid-friendly friends. And if you really want to score some points, plan to host a sleepover at your place.

But you have to make sure you’re actually presenting them with something day-of. Like, if you’re taking them to a Red Sox game, maybe throw in a couple Sox T-shirts to sweeten the deal. Your gift will almost definitely be overlooked in the heat of the gift-opening, outshined by piles of said plasticky garbage, but that’s OK. Any old uncle can shine on Christmas day. Only a Cool Uncle knows enough to sprinkle reminders of his coolness throughout the rest of the year.

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