6 Things You’ll Learn From Dating A Younger Man


You meet him at a BBQ. 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 younger sister.

A few nights later you go for drinks at a chic wine bar. He insists on ordering a nice bottle of wine 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.

1. He has little to no relationship baggage. You’ve never dated a younger guy before. After attempting to date a variety of divorcees and single dads in their 30’s and 40’s, 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.

2. 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. You take care of yourself and know you look really good, 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. However, you quickly come to your senses and you tell yourself, “What the fuck?! I mean, what the fuck? You’re awesome!” This is a huge red flag that you decide to ignore in favour of enjoying his abs for just a little bit longer.

3. When it comes to sex, he’s all youthful energy minus the finesse. This is exciting. Maybe you’ll be able to teach him a few things in the bedroom?! However, the flipside of this is that you have to want to learn to be a good student. Two minutes into one of these “lessons,” you ask him how he’s doing. He replies, “Oh. I came a few minutes ago. That’s why the girl always has to come first. Sorry, totes Awk.” (Awk for him, maybe?)

4. It’s not just the sex he abbreviates. He abbreviates everything to the point where it feels like you’re talking to a text message or living inside an Entourage script. His texts sometimes feel like they’re written in morse code. You spend far too much time trying to decode his text messages thanks to help of Google, Urban Dictionary and desperate pleas to friends, “What does @TEOTD WYMH mean?!”

5. He makes you feel like you’re living in your very own Katy Perry song. Despite this “awk” gap in communication, you like how he makes you feel young and fancy free—all butterflies and giggles and Teenage Dreams. It’s only later that you realize the reason he makes you feel this way is because you do things that teenagers do: you smoke pot at the beach, you smoke pot in his backyard while wearing his hoodie and you make out in his mom’s car while parked down by the marina.

6. You have very different ideas of what constitutes a good night out. The romantic night you spent at the wine bar was an anomaly. You start to seriously question your dating choices when he suggests one night that you fill a couple of water bottles with booze and head over to the local rec centre to go swimming while you get drunk in the pool. When you imagine getting drunk within the overheated, chlorine fume filled confines of the same building where you took childhood swimming lessons, you can’t imagine anything worse.

“I’m 33. There’s no way I’m doing that,” you tell him.

Your friends start to question your dating choices when, after a night out at a local cocktail bar, he texts you and suggests that meet him at the 24hr McDonald’s up the street—the one frequented by teen meth heads and vagrants.

“What the fuck? I mean what the fuck?” they tell you. “You can’t go there. You’re too awesome and you’re wearing Miu Miu.”

When he breaks things off with you, he does it without letting you know. After a month of dating, one day he just stops returning your texts. You’ve heard your 20-something friends complain about similar break-up tactics.

“Is this a 20-something guy thing? I mean, what the fuck? Why is he still liking all my Instagram photos?” you ask your friend.

However, eventually you come to the conclusion that this isn’t a 20-something guy thing, but merely a lame-guy thing. Have you been dating a lame guy?

I mean, what the fuck.