The 5 Types of Guys You’ll Date After I Date Them First

Chances are you’ll be dating a few different types of guys in your twenties—guys that I got to way before you did. Whether it’s the skater punk, the gym rat, or the mama’s boy, I’ve already dated them and can tell you exactly what their deal is ahead of time. It’s so cute that you’re cycling through my leftovers, though! Enjoy!


The Brainy Hipster (Who I Dated for Like Eight Months)

You’ll first spot him sipping on a latte at the trendiest coffee shop in town, flipping through the pages of Infinite Jest. If he’s anything like I remember him, the two of you will spend hours watching classic films and annoying all your friends with your constant, witty banter. It may seem fun now, but you’ll realize how pretentious and boring he is any minute now. While I have you—can you return this copy of Casablanca to him for me? He left it at my house.


The Party Animal (Who I Used to Hook Up With)

He’s the life of every party, and all my friends—sorry, your friends now—love him. You’ll initially find his boyish charm endearing, but eventually his man-child ways will start to get tedious. I mean, at least it did for me. He was adorably pathetic when I broke up with him. I’m sure you guys are great together, though! So glad he’s bouncing back.


The Funny One (Who I Signed Two Leases With)

This guy always has you cracking up with his impressions and hilarious one-liners. His Christopher Walken impression is amazing, right? I mean, it probably seems that way now. Even though you adore his sense of humor, you’ll find (as I did) that it’s very difficult to have a serious conversation with him. For example, when we were living together, he avoided discussing our finances like the plague. Don’t worry, we’re totally just friends now. Tell him I seriously LOL’d at his text on Saturday. I’d explain, but it’s kind of an inside joke!



The Corporate Guy (Who I Almost Married)

He’s the Wall Street Journal-reading, briefcase-toting guy who seems like he might be The One. You love his ambition, and his financial stability doesn’t hurt, either. Hearing him discuss his career goals and 401k might be oddly hot at first, but honestly, he just wasn’t good in bed. The one sex thing he does well is something I taught him, so you’re welcome in advance! Ultimately, you’ll realize he cares more about his career than he does about you. I know this for a fact, because I’ve lived this all before you.


The Musician (Who I Still Hook Up With Sometimes)

He’ll sweep you off your feet with his acoustic guitar, and if you’re anything like I was you’ll fall for him fast. His shaggy hair and flannel shirts are a breath of fresh air after the stuffiness of Corporate Guy’s fresh-pressed suits. But once his indie-alt band finally started getting gigs, you’ll have to start competing with groupies for his attention—I know I did! Once you break things off, he’ll still be a reliable every-so-often hookup whenever he’s in town. Before your first date, listen to his song “My Perfect Girl”—he wrote that one about me a few months ago!


Sometimes you have to do a bit of searching before you find Mr. Right. And that means sifting through the guys I’ve already dumped. Trust me, you’ll learn something from all of these guys, as I already did wayyyy before you!