Things You Will Learn From Dating a Younger Man

by Skinny Dip on August 21, 2014

On July 1st you receive an email from your ex in Toronto – the one you left behind when you moved back to the West Coast – letting you know that he’s met someone and in a few months he will be a father.

The news throws you – not because you aren’t happy for him – you are (he will be a kick-ass dad) – but because this is his dream. The dream he wanted for the two of you. The dream that you couldn’t deliver on for him.

Clutching your smartphone, you break down in tears in the garden section of Capital Iron, while your Mom strokes your back and asks you what’s wrong.

You haven’t lived in Toronto in nearly three years, however you cry because in this moment it feels like the life that you used to have there really is over. Although the future is exciting and exhilarating, it’s also kind of fucking scary.

The future is happening right now.

Although you feel slightly untethered, you decide to slap on some make-up, put on that new dress and go to a Canada Day BBQ that you’ve been invited to.

Dating a Younger Man
Your friends pick you up in a 1950’s mustang convertible. Disclosure is playing on the stereo. Driving along the beach as the warm air rushes past you, life feels oddly perfect.

At the BBQ is where you meet him. You notice him right away because he has what some people might call “swagger.” He’s tall and athletic looking with a strawberry blonde Macklemore haircut. Acne scars faintly dot his chin.

You hear him talking to some other people about Toronto, at which point you join in on the conversation. It turns out that he used to live there, on the same street as you – just a few houses down from the gorgeous brownstone that you used to share with your ex. What are the odds? This must be kismet.

You’re on your third hot dog of the evening. He’s eating ribs. When you notice him scrambling with his hands full to pick up another beer, you politely offer assistance.

“Would you like me to hold your bone?” you ask.

“Yes, please” he replies.

You talk some more. You laugh. He comes with your friends to watch the fireworks from a cliff overlooking the ocean.

It’s only later that you learn that he’s six years younger than you and went to junior high school with your baby sister.

A few nights later you go for drinks at a chic wine bar. He insists on ordering a nice bottle of wine to share and picking up the cheque. You’re impressed.

You laugh. You kiss. You have sex. You wake up wrapped in his sinewy tanned arms and think,

“I could get used to this”

By midsummer you’ll change your mind and you will no longer be dating. However, before that happens you’ll learn a few things along the way.

You’ve never dated a younger guy before. After attempting to date a variety of divorcees and single dads, you’ll find this guy’s total lack of relationship baggage utterly refreshing. However, you’ll soon realize that the flip side of this is that he seems to have no serious relationship experience whatsoever. This starts to reveal itself quickly.

Dating someone younger often means that their exes are young too. When you stumble across a photo of his ex-girlfriend on Facebook, you discover that she looks like a younger, firmer, more proportional Kim Kardashian. It gets worse when he tells you that they broke up six months ago – right before her 19th birthday. Now, you know you look good for a 30-something, however when you don’t hear from him for a few days you start to wonder if maybe he finally noticed the fine creases on the corner of your eyes and promptly got freaked out.

[click to continue…]


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