Your twenties are a time for exploration, for making mistakes, and for figuring out the kind of person you want to be—and be with.
Most of us date more than a few people in our twenties, and that's good! It let's you realize what you want out of a relationship and the type of person you want to end up with.

And in that case, you'll probably recognize some, or all, of the guys on this list of Winnipeg guys every girl dates in their twenties.


1. The Voyageur

He lives for Festival Du Voyageur and whispers romantic French sayings into your ear (at least you think they're romantic). After a few passionate months together and more than a few pounds gained from all the poutine you ate at Le Garage, you say au revior to his beautiful beard.


2. The Rich Guy

He takes you to 529 Wellington for your birthday, your one-month anniversary, and 'Just Because It's Tuesday". You'll miss his Tuxedo condo and the weekend ski trips to Whistler.


3. The ‘Good-On-Paper’ Guy

You decide to go visit your parents and he's already there, eating dinner with them. Turns out they do it every Sunday night. Turns out his master's degree from U of M and his RRSP are the only mildly interesting things about him. (Also turns out that after you break up with him, your mother will continue to invite him over for Christmas Eve dinner for years to come).


4. The Player

What attracted you to him was his insane bod and his perfect response to everything you said. But Winnipeg is a small place for a player to play, and when he went to the bathroom at Smith, the bartender told you he was here a few hours ago with a different girl. Boy bye.


5. The Kinda-Older Dude

You're 24. He's 32. It feels like the mature relationship you've been waiting for, but really it's just a lot of movie nights at his Waterfront condo, awkward nights out with your friends at The Pint when the bouncer asks "is this your dad?", and you skirting around the topic of marriage.


6. The Barista Dude

What attracted you to him was the way he looked in his raw denim jeans (and his ability to whip you up a mean soy latte at Parlour or Thom Bargen). What ended it was his inability to discuss mainstream culture and consumerism without breaking out into hives.


7. The Bartender

You probably met at a Corydon cocktail lounge or Earls wine night with the girls. After dating for a few weeks, the only thing you've learned is how to pretend to like negronis and that he's only really cute in dim lighting and a black button up.


8. The Workaholic

After the bartender, you're looking for a guy with a little more drive and dedication (and a regular sleep schedule). The workaholic seems great at first— until you open your eyes mid-makeout and realize he's on his Blackberry while he's on you.


9. The Friend-Zone Guy

He's the one you call on that random Friday night in November when no one else wants to go out, or that week in July when everyone's away at Folk Fest or Countryfest. But it'll never go beyond a sloppy one-time makeout at the Pal, as much as he wants it to.


10. The Club Boy

You met at 441 Main or Nectar on a Saturday night. Then, when you made it official, he STILL went to the club. Without you. Every. Single. Weekend. Zero Netflix and chill for this guy.


11. The ‘Still In Love With His Ex’ Guy

He mentioned her once or twice on the first date. You know he still follows her on Instagram, and still watches her drunken stories from The Toad on Snapchat. Finally, he breaks down while skating on the frozen Red River, sobbing, "this is where she told me she loved me". A grown man crying in figure skates is one image you wish you could forget.


12. The Gym Buff

Most of your dates involved meal prepping, sweaty nylon and lycra fabrics, and an intense discussion on isolation training verses compound lifts for strength development. You've never looked better.


13. The Guy Who Calls You His GF After Two Dates

Your first date is brunch at Stellas, because he "loves the way your face looks in the morning". On the second date, his friends 'happen' to walk by, and he introduces you as 'his girl'. When he drops you off, you get a Facebook notification before you're even inside that you're 'in a relationship'.


14. The Mamas Boy

He picks you up in his mom's SUV and takes you to a St. James restaurant "he knows you'll love because his mom goes here all the time". When he starts to tell you how great you'd look with a Kate Gosselin haircut and a collared blouse, it's time to leave.


15. The Selfie King

The guy you thought was cute until you found his Facebook and realized it's chock-full of mirror selfies in the same dirty bathroom with rotating outfits. He may be hot, but he knows he's hot and he wants the world to know it, too.


16. The Country Guy

You're still not sure how you met him, seeing as he grew up in a town like Oakbank or Grunthal and mostly frequents bars with the word 'hotel' in their name. Regardless, he knows how to rock a pair of cowboy boots and looks hot AF driving a truck.


17. The Guy Who’s Got His S**t Together

You've never questioned your motivation, savings, or organizational skills before, but this guy's got you beat. He graduated high school early, had his own start-up by age 19, and makes time for the gym, beers with the boys, and weekly trips to see his grandma in Transcona. But you, in your twenties, aren't quite ready for him just yet (you still drink too much on a Wednesday night and occasionally iron your shirt with your hair straightener).


18. The Sports Fan

He wears at least one type of Jets gear at all times and a regular Saturday night for the two of you is you watching his beer league hockey game at the Iceplex. You learn a lot of useless stats during your time together.


19. The Skater Dude

You met him where he works at Sk8 Skates, Green Apple, or Kings. He's always filming skate vids or starting clothing companies or doing something counter-culture cool. You always knew he'd be underground famous someday, but of course it had to happen after you two broke up.


20. The Weekend Guy

Neither of you are too keen on a relationship with each other, but you always end up at the same parties and you know the other is always available if you need a plus one for your cousin's wedding or work christmas party at The Met.


21. The Lowkey Guy

You're in a full-on relationship and you've practically moved into his place...except he's never met your friends, family, or seen your apartment.


22. The Perfect Guy

He's out there (probably, if you believe in that sort of thing). And he'll probably be a combination of some (or all) of these dudes that you dated in your twenties, but seemingly handpicked just for you.
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