Ask TSJ: Digging On My Son’s GF


LIFE IS HARD. It seems like every new day brings a new question that, try as you might, you’re just unable to find an answer for. The Smoking Jacket understands this, and we’re here to help. TSJ’s editor, Melissa Bull, and Headshots’ columnist, Mike Spry, set aside some time in their busy schedules to answer your questions in a feature we’ve cleverly named “Ask TSJ.”

This week’s incredible question comes from our a friend in need in Toledo. And you know what they say about a friend in need is a friend indeed.

Hey TSJ-folk,

Help. Please help. Help me please. Please.

Somehow, I’ve begun an affair with my son’s girlfriend (nothing illegal, she’s 20 and I’m 39). Problem is, I think I’m in love with her. My son’s mother and I are long-since divorced, and the kid’s a bit of a douche so I’m not worried about hurting him. My real problem is the age difference. Like, what’s a Taylor Swift? And who is Katniss? And why are condoms flavoured now? Is there some quick reference guide you can provide?


Ray in Toldeo




Dear Ray,

You know what your problem is? Imma tell ya. Your problem is that you need to know that Taylor Swifting stuff don’t matter a whiff. Millenials just need to be told they’re SOO PRETTY! SOO SPECIAL! OMG THEIR HAIR IS AMAZING!! Ya man. Tell your son’s foxy GF you just want to be FAIR, and SHE DESERVES ONLY GOOD THINGS! And she’s so great! And does she need a pedicure yet?

You got so much taboo sugar-daddy cred right now and you don’t even realize it.

I would rather be sacrificed to zombies than date a millenial, myself, but unlike you, I’m not vying for any father of the year award.

Oh yeah, that. So like don’t date your son’s lady. Date her BFF. Think about it. That’s the ticket.




A 19 year age difference. Well, well, well, Raymond. Aren’t we just the cat’s pajamas, the bee’s knees, the cock of the walk.

I’m going to go ahead and guess that you’re either a professor in an Arts and Sciences faculty or a writer of some sort, but not very successful.

There is no guide for this endeavor, no quick reference guide for trying to sort out why she wants you to take her to a movie about vampires who date werewolves and sing in a pop band. If you stay with this woman, and if we use history and logic as a guide we can safely assume that she’ll ditch you the second you turn 40, then the entirety of your life will be spent pretending you’re younger and dumber and less road weary than you are.

Enjoy it while it lasts, Ray. Enjoy the tight body, the envy from your golf buddies, the never-ending trips to the pharmacy for Viagra. In a few months she’ll be dating a poet from New Brunswick who just got his MA, and you’ll be sifting through online dating sites and trying to reconnect with your son.

- Mike

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