Woe Is Me! “I Have a Crush on My Ex‑Boyfriend’s Father. What Should I Do?”

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Nov 24, 2019

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Woe Is Me! is a series in which The Swaddle team indulges your pity party with advice you’ll probably ignore.


“I have a crush on my ex-boyfriend’s father. We dated for two months before I met his father in person, and fell for him in the very first conversation he had with me. I couldn’t continue dating the son anymore because I liked his father way more than I liked him. He’s married and his wife is really nice too; I’m quite fond of her. We’re family friends and often bump into each other at social functions, which have currently become super awkward and uncomfortable. Do I tell either of them? What should I do?”

— Dadbod Enthusiast


SM: Why am I picturing Anarkali, Saleem, and Akbar having a weird dance-off at a cocktail party? Anyhow, I don’t see what purpose telling either of them will serve, other than becoming a potential plot for a Karan Johar-meets-Anurag Kashyap film (dark but glamorous but not Bombay Velvet). Sorry, Dadbod Enthusiast, but some woes we just have to live with! Maybe you could write about this, and that could make for great content?

ADT: YIKES. So, honestly, this isn’t super gross — way too many women find themselves attracted to older, successful men. If you’re in love with him, that’s an embargo on family functions and meeting this ex till you’re completely over it. If its just attraction, you could put it in a brain pocket and maybe pull it out for a day of *ahem* self-care? What ex-boyfriend and his dad don’t know won’t hurt them. Embrace your dark side a bit, Dadbod Enthusiast – we all deserve it.

PP: What should you do? Nothing. Absolutely nothing. Let this be a crush — it can stay as a feeling of attraction you have towards the dad or it can go away as crushes and infatuations do, especially when they’re highly implausible. Liking an ex again is bad enough, liking his very-married father who is happily married to someone else — and then confessing it — is a recipe for disaster. Not only will the father be put in an awkward position of having to acknowledge a woman he likely sees in a daughterly way pining away for him, but the wife will also be made uncomfortable.

As for the ex: my gut feeling says it’ll propel him into dark depths of toxic insecurity about his masculinity vis-a-vis his father. I mean, first his mom and then you?! Even Freud can’t salvage that damage. So, yes, do nothing about it and whenever you bump into them at functions, make small talk about how everyone is and then very consciously, extricate yourself from it, and leave. Let this one go, bub.

RD: Every crush doesn’t need to be realized into sex or dating; a big part of feel-good crushes is also flirting! I suggest you keep bumping into him at functions and indulge yourself (maybe watch how much you drink because it’s more difficult to know what the line is when inebriated) by speaking to him and engaging with all the qualities that attracted you to him in the first place! It might make him feel great and might make his wife think her husband has still got it.

And the son? Well, if he hasn’t caught on by now, he probably never will. This way, you get to have your fun and still don’t cross any societal boundary. I guess what I’m saying is, your woe isn’t a woe and you should simply enjoy basking in this dude’s charm. And yeah, listen to ADT — self-care when flirting isn’t enough.

AM: Are you ever going to be able to tell him that you have a crush on him? My guess is a no. And neither are you going to be able to tell his son or anyone else in the same social circle. If you were planning to, just don’t. It might get very messy. So, considering this, keep thinking of it as a crush till you find someone with similar personality traits who might make you forget this dad crush!

LG: No, you shouldn’t tell either of them, because dirty little secrets are what add spice to life and keep us from hurting people. But as for what should you do? So many things. Flirt your brains out, a la RD’s recommendation, and start thinking of the awkwardness as sexual tension. (Fwiw, significantly older gray foxes are my favorite demographic to flirt with.)

Alternatively, get a voodoo doll and use it to facilitate a perfectly amicable divorce between Dadbod and Lovely Wife for reasons entirely unrelated to you but which end up driving him into your arms anyway. What else? If you’re artsy, sketch his face onto your vibrator (bonus if Dadbod has a bushy mustache). Browse PornHub until you find a Dadbod doppelgänger and hole up in a hotel with high-speed internet for a weekend (bonus if you bring the vibrator-portrait). I mean, there are plenty of things to do, and all enjoyable; why so hopeless?

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Written By The Swaddle Team

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