The 20 guys you'll date in your 20s

Dating in your 20s is a wonderful learning experience during which you get to meet, dine with and possibly date a wide variety of interesting and wonderful men. If you haven't, it's because you've settled for your university sweetheart, no offense. Because we've all seen Sex and the City seasons 1-6 over 85 times and He's Just Not That Into You just isn't a philosophy we subscribe to, we've come up with an extensive guide to dating in your 20s. At the risk of alienating every guy we've ever dated, we present to you our list of the 20 guys you'll date in your 20s and what to expect. Enjoy.

The Artist

You'll meet the Artist at a gallery opening where his perfectly tousled hair is gently concealing the fact that he hasn’t showered in three days. You imagine touching his meaningful tattoos, his paintings are actually really good, he "gets you," he’s sensitive, he promises to paint/photograph you. Next thing you know you’re posing in your underwear in his studio/loft conversion. Hook, line and paint-her.

Cons: Just face it—he smells. He wants to spend long periods of time eye-gazing and talking about feelings. He’s broke. He uses words like "transcendence" and "caveat." He has a legitimate excuse to hang out around naked women all day. His idea of a suit is a corduroy blazer. He listens to really depressing music, although if you like Bon Iver and/or songs about suicide and abortion, I guess this is a pro.

Advice: The nude photo shoot you thought was a good idea when you were 19, RARELY IS. Five to seven years later when he sends you a 16 x 40 collage of your breasts, you’ll know what I mean.

The Doctor

Doctors are extremely tempting to date because on top of being able to prescribe any medication you want, they’ll do adorable things like check your pulse when you’re making out and they really do understand a woman’s anatomy. They are also very interesting to talk to, make a good living and tend to be borderline alcoholics, which means you get to drink the expensive wine, and a lot of it.

Cons: Doctors are nerds. Don’t be fooled by the rich, handsome doctor appeal, this is the exact same four-eyes science geek whose chemistry homework you copied in high school. He thinks that liking the Red Hot Chili Peppers makes him cool. He can be boring and too pragmatic and even if he tells you otherwise, he has absolutely looked up your provincial medical file before the second date.

The Hipster

You’ll be drawn to the Hipster because of his sweet vintage boat shoes, great taste in music no-one has ever heard of and wacky (fake) glasses. His pretentious attitude will make you feel like you’re the only person in the world he can stand and this will make you feel superior, fleetingly.

Once the PBR buzz wears off you’ll realize you’re sitting in a really shitty bar with no windows, drinking the cheapest beer, surrounded by 30 people who are all wearing the same fucking plaid shirt and stupid glasses, talking about ways to like Sufjan Stevens even though he’s religious, and comparing "no I hated art school more" stories.

How to dump him: Tell him you like the Katy Perry's music. A lot. Which, lets face it, you do.

The Professional Gambler

The '"lucky in cards, unlucky in love” adage is painfully true, so there’s really no upside here. Dating these guys is an emotional roller-coaster that goes up and down with the spreads on Their idea of a romantic night in is having you over to watch World Series of Poker until 2 a.m. Over-under on this relationship is about four dates.

Best case scenario: The guy takes you to Vegas or Atlantic City where he ignores you to play craps (the “best odds”) for literally HOURS ON END while you drink the free watered down vodka sodas a woman in a metallic bustier and nude tights brings you every time you get close to seeing the bottom of your glass. The best way to get through this is to get gifted a few hundo in chips and try your luck at the poker table. You may wind up getting really fucking good at poker, which will emasculate him in the short term but payout eventually when you dominate poker nights with other guys at future charity events.

Worst-case scenario: This guy will be addicted to online sports betting and bet on everything from horses to hockey to baseball to European futbol. The mood of your dates will be 100 percent determined by his balance on, which fluctuates constantly while he indiscreetly checks scores on his iPhone throughout the entire meal. Risks he is not prepared to take include going “all in” on one woman so you can be sure he’s hedged his bets with some sure things on the side.

Advice: Never turn down an opportunity to go to the horse races, betting is pretty fun when you don't have a debilitating gambling addiction, but cash in while you’re up, the house always wins.

The Lead Singer of a Band

There is little-to-no way around the fact that this is a one-night stand. Depending on how famous he is, this can be a real thrill and once your hangover wears off, your ego will be soaring. If for some reason you manage to actually date a lead singer, keep in mind that "LSB" also refers to the extreme narcissism personality disorder associated with all such individuals and extreme caution (read: condoms) should be used at all times.

Pros: He’s really fucking hot, he’s famous, every girl in the room will be drooling when you leave in his limo and it’s a great story to tell. He will immortalize you in ballads that will make you swoon/cringe. Sometimes you get to make out with him on stage.

Cons: Musicians tend to be really unstable drug addicts with major psychological issues. If you don’t believe me just wait until it’s 7 a.m. and your once hot and charming musician guy is now crying naked, chain smoking and doing lines off the Much Music Video Award he won last year talking about how nobody cares about him now that he’s rich and famous.

He also doesn't believe in sheets, and when you sleepover (only known as "crashing" from now on) his roomate/bassplayer will steal money from you to buy heroin. He will have a pretty disturbing pectoral tattoo. At some point he will lose interest as quickly as he became obsessed with you and stop returning your calls. This may also be because he was too broke to pay his phone bills so don't take it personally.

The Frat Guy

You’ll fall for the frat guy because in addition to being good looking, athletic, and fake tanned, he’s also pretty funny. Something about engaging in nauseating Greek traditions, womanizing and homoerotic dress up activities makes this guy super fun. A word of caution though, just because he looks hot in a pastel gingham button up and honestly listens to Taylor Swift doesn't mean he truly understands women or his racist/homophobic/misogynist jokes are acceptable. Sure, watching the Bachelor every Monday night in his filthy frat house is fun, just don't leave your white wine spritzer unattended for a millisecond.

Cons: He secretly wishes he was gay/you were in a sorority. He wears terrible clothes emblazoned with his frat logo, he’s a womanizer, he probably has an STD, he lives in a shitty frat house, his sheets smell, he genuinely prefers the company of men to women. In a couple years he'll become The Real Estate Guy.

The Real Estate Guy

There are two things in common with all Real Estate Guys; they all like scotch and they all work on commission. You can always tell how well a Real Estate Guy is doing in business by the type of scotch he has in his liquor cabinet. Get him at a bad month and he's drinking Johnny Walker Red out of a paper cup. Catch him at a good time and you're both drinking Blue Label and Macallan 25 out of the good crystal.

The same goes for all aspects of his life. Sometimes he's up and sometimes he's down. This constant teeter totter means that he can be spontaneous and a little all over the place. So don’t think when your honey shows up with a new Ducati after a normal Friday that he’s been saving up for that for months. In reality, he just closed a deal and got a monster commission. It doesn’t need to be said that he's impulsive and willing to spend a lot of money to prove it. If you like excitement, the Real Estate Guy is a great call. On top of being charming and fun, he is charismatic, has a winning smile (as evidenced on his cheesy business cards and bus stop advertisements), and knows all the good restaurants in town.

On the downside, he has slept with most of the waitresses at Cactus Club, so unless you are one, you might want to consider how much you love the Bandara Salad before going out with him. And, of course, when you break up you have to deal with seeing his fucking name plastered outside every vacant property in the city.

Because in business he has to have more than one property on the go at all times, he's transferred this philosophy to dating and he will always have a couple girls on the back burner that he's negotiating deals with. For both reasons, he's addicted to his Blackberry. Even if Megan Fox was in his living room holding a suitcase full of cash telling him that Bill Simmons is in the other room talking to God himself, he would not give it up. And it’s password protected, just like his computer, and the password is I AM AFRAID OF COMMITMENT.

The Young Guy

In your later 20s you will change some of your policies on dating teenagers due to disillusionment with the above individuals.

The Young Guy is adorably unaware of the typical emotional witholding we have become accustomed to and later realize is actually a good thing when he texts you short essays on his feelings/your lack of feelings five plus times per day.

What the Young Guy boasts in terms of sexual vigor and enthusiasm he lacks in experience, so be prepared for a lot of female anatomy lessons in the bedroom. Because of his endearingly earnest adoration you will overlook redflags such as making you a painting entitled "Diagonal Sunset with Black Roses" or having a giant back tattoo of a coiled boa constrictor which upon first incredulous glimpse you will utter, for the first time in your entire life, the phrase: "please be back hair."

The Old Guy

You don't have to "wish" for backhair here since that is pretty much guaranteed. In much the same way that the under 22s were off limits, eventually you will also open up your "heart" to the Old Guy. In contrast to Young Guy, these men are very low maintenance because they've seen it all before/are probably dating three other twenty somethings in addition to having kids and an ex wife.

Pros: He is pretty interesting, the shocked looks on restaurant patrons make you feel young and rebellious again, you get to wake up in posh hotels and order room service in the morning or if you stay at his place, his maid makes you eggs and discretely folds the lingerie you left strewn on the steps on the way in. So you get to feel pretty dignified.

Cons: Viagra is no longer a recreational part of your life anymore but rather a nightly necessity. He's had a vasectomy so if you were to get serious your only chance of procreating are the preserved sperm popsicles in the back of the freezer.

The Surfer Dude

Also known as the Unemployed Guy, this guy is tanned, buff and is suuuuuuuper chiiiill bro! You will date him because all those pop ups make for the abs of a male Adonis; he's into yoga, Wes Anderson movies, Jack Johnson and thinks peanut butter banana burritos are an appropriate dinner food. Obviously he is always stoned.

Hanging out with him is similar to taking an Ativan. His presence is calming and he will make you feel good about yourself. You feel like you can confide in him because he’s a good listener. Did I mention he’s tanned?

Cons: He’s not a good listener, he’s just really really really dumb. By the age of 30 his tan has turned into skin cancer and he has lots of gross wrinkles. You’ll have to put up with him going to Cooooosta twice a year and when he’s not in Coooooosta he’s talking about how amazing Cooooosta is.

The promises of "teaching you to surf" where you envisioned a Blue Crush-esque scenario involving Michelle Rodriguez and a dog on a surfboard, will actually consist of you getting slammed by waves until you wash up on the shore two miles away from your bikini top. He will abandon you every time it's double overhead so be ready to spend the day trying to discretely get sand out of your vagina whilst trying to look like a seductive siren tempting him ashore.

You will also see fluids come out of neat places, like when he casually pees in front of you at the beach and it comes out of the ankle of his wetsuit, and in bed when latent seawater leaks from his sinuses onto the sheets in the middle of the night. FYI you'll spend a fortune on fake tanning to match his year-round glow.

How to dump him: Next time he goes to Tofino to spend eight hours wearing a hooded wetsuit to catch one or two waves in the freezing fucking rain and eat whole wheat vegetarian pizza after, throw on your Canucks jersey and head to a sports bar, where you’ll meet The Former Jock Now Sports Fan.

The Former Jock Now Sports Fan

The Former Jock Now Sports Fan is easy to spot. Maybe he’s busted both his ears playing rugby, has a telltale wacky nose from playing intramural hockey, or just has a great body. In short, any guy who is at least six feet tall and is rocking a busted face or is wearing a (duh!) jersey are all good signs you’ve found the Former Jock Now Sports Fan.

Pros: If you like watching sports then you’ll always have someone to watch the games with. He is an encyclopedia of sports knowledge and you can learn a lot from him and then use his lines/opinions to impress other guys. In extremely rare cases you might find one that has seasons hockey tickets, although if this ever happens, chances are he’s the dreaded Spoiled Trust Fund Guy and that’s a whole other story.

Cons: You have to watch sports every single god damn night. He doesn’t drink wine. Sometimes he’s a bit out to lunch and you can’t quite place why—it’s because he has had at least three concussions and has subsequent brain damage. He not-so-secretly wants to marry an athletic woman so that his kids will be good at sports. He genuinely loves hot wings.

The Spoiled Trust Fund Guy

You met him at a charity event. He has 17 pastel polo shirts. His teeth are sparkling white. He plays golf in sweater vests. He went to private school then did four to five degrees because his parents could afford it and he hated the idea of giving up spending summers abroad. His mother drinks more chardonnay than you do. He has a tennis court in his backyard, a stable and a pool. At first you think you’ve hit the jackpot.

After the initial couple yacht rides wear off, you’ll realize this guy still lives in his parents basement, country club food sucks and you’re dating a conservative prick who hunts and thinks that reading The Economist makes up for the fact that he doesn’t have a job. While at one of his various summer homes you’ll inevitably realize no amount of gin, monogrammed towels or the good cheese can make up for the fact that you’re dating a spoiled little brat with no real direction in life.

The Finance Guy

The finance guy is the Professional Gambler but with a real job. If you live or have lived in New York this is all you've ever dated, so you probably think all men sleep four hours a night, swear like sailors, drink like fish, smoke like chimneys and do coke like Lindsay Lohan. These are the Frat Guys aged 10 years physically but no more mature emotionally. They still prefer the company of men, are highly competitive and "get to be" assholes all day on the trading floor. They are alpha males and proud of it. They are pretty smart, ambitious and extremely entitled. They take cocky-funny to a whole new level, and their confidence, hilariousness and ability to look like Don Draper in a suit can be pretty irresistible.

He is in the type of industry where he can actually charge bottle service at a nightclub to his company if he’s "with a client" and this can be fun. If you're dating this guy you're probably pretty used to being among the 4-12 women at a given Finance Guy's table at whatever is currently the hot spot. He'll make sure you catch a glimpse of that $400 price tag on the wine he ordered and cars he sends for you to meet him at the club/Cabo.

Don't forget that just like the stocks he trades and the magnums he buys, you are a commodity, so enjoy dancing on banquettes while you can.

Cons: No matter how fun dancing on a table while a handsome guy pours Grey Goose down your throat is, this guy has one major con. He’s married. He takes his wedding ring off every Thursday night in order to pick up na├»ve girls like you. Move along.

The Lawyer

This guy gets by on the fact that he works in a seemingly noble profession and works really long hours. He’s smart and can make a pointed argument. This can make for some lively conversations, witty banter and you can’t help but respect him. Also, of course, free legal advice.

Just don’t forget that being a lawyer means he either tries to uphold the law or get around it for a living. This means he’s either extremely self-righteous or really good at manipulating situations, probably both. He's always right (obviously) and to drive home this point he'll litter his correspondence with really big words he thinks you won't understand. He works until 10 p.m. We often refer to this guy as the cops/metermaids of the wealthier/slightly smarter crowd.

Advice: If you really want to date a lawyer the only choice you have is to become one yourself. Lawyers only have successfull relationships with other lawyers. Then you can both work until 10 p.m. and spend the rest of your lives judging others. If you're not a lawyer keep in mind that when he says the two of you are not concomitant and calls you a vitriolic bad influence that he must abscond from, he really means that he wants to dump you. Save yourself the trouble of looking up those words in the dictionary and head to your neighbourhood bar for some much needed ego reparation from the Actor/Model (aka the Waiter/Bartender).

The Actor/Model (aka The Waiter/Bartender)

Trying to make this guy like you as much as he likes himself will be pretty much impossible so it’s best not to try. Chances are he’s much better looking than you and considerably less intelligent. You’ll want to take him to places and events where lots of people will see you together but you don’t actually need to have a conversation with him. Nightclubs, movies, and charity events work best.

Pros: He works in a bar or restaurant so that means free drinks! You can traipse in after hours while he does his cash-out and compliment his money counting skills while secretly correcting the math he does wrong. Simple-minded people tend to be pleasant company and if he ever finally gets an acting job, you might meet Ryan Gosling.

Cons: Actors are extremely self-absorbed and their emotions are all over the board because of all the auditions they have to go to/jobs they don't get. If he's ever actually been in a movie, he will make you watch it over and over and over again. Keep in mind that he acts for a living, which means he can lie through his teeth. In fact, he may truly believe that lying is just a daily way that he can practice his craft. Most importantly, dating a guy who has better hair than you is bad for self morale.

The Ad Man

If we've learned anything from Mad Men it's that we shouldn't date guys who work in advertising. I don't need Don Draper to vomit on himself again to know that this isn't a good idea. Still something about men who work in advertising can be pretty exciting. For one they are really good with words, which means they are really good at texting. They are masters of the pitch, which means they make great first impressions. Most importantly they know the difference between manipulation and marketing to a demographic. So while their tactics might seem contrived, at least they care enough to think they've got you all figured out, which of course, they don't.

Cons: One of the only real cons to dating someone who works in advertising is that ever since Mad Men happened, he thinks he's really fucking cool. This has led him to have a bit of an inflated ego. When geeks first realize they might be either cool or really rich, the first stop on their train to awesome is usually to date a model. The Ad Man has probably dated a couple, which basically just means that he can stand anorexics and is tall. So no worries there.

The Gamer

There is nothing wrong with dating guys you met online. Some of our friends met their soulmates on dating sites, and just because all of them have since divorced doesn’t mean they didn’t enjoy some wonderful caring months as man and wife.

The problem with dating a gamer is his online life is always more important than any possible RL experience. In RL he’s broke, but online his World of Warcraft character has 1M gold. He has no discernable RL work-applicable skill set, but his WoW character has gotten to 70 and can lead parties into instances like a digital Elf version of General Paton. He lives in his grandparents’ basement and takes the bus, but on WoW he has l33t amour, the sword of 1,000 truths and a flying mount.

While at first it seems funny and charming to learn new words, the novelty wears off pretty fast. Make no mistake, Role Playing Game does not connote you dusting off the old high school kilt to these guys. While it’s fun to be the first human girl he's touched possibly ever, your relationship is best saved for lol links to memes and authentic-sounding vocab tips for blog posts making fun of them.

The Girl

So there may come a time when men begin to lose their appeal, and whether it’s because someone put MDMA in your drink or you’re just a little bit gay, you’re going to hook up with a woman. The upside to dating a woman is that most men won't consider this cheating, so if you're in a relationship and looking for some excitement on the side, a woman is definitely the way to go. FYI you're going to have to listen to a lot of Katy Perry in order to psych yourself up for this. Pictures may end up online, it may be a black-out blur but you're pretty sure it ruled—just listen to Katy Perry’s TGIF at this point.

The Good Guy

You will occasionally come across genuinely nice guys who respect you. He loves golden retrievers, he wears khakis and has a great relationship with his mom. He probably even owns property and considers women equal to men. Gasp! He'll usually introduce you to his friends and family within an appropriate amount of time, he doesn't have any weird emotional issues and he genuinely wants a committed relationship.

You'll think he's cool, smart and interesting but because you're emotionally stunted, instead of dating him like a normal person, you will decide he's friend material, lead him on for years until he eventually marries someone else and you realize your “backup” is gone and you are alone. Woops.

The One

We've listened to enough Taylor Swift songs to realize that this guy might exist, and if he does, he might look a lot like Taylor Lautner. Unfortunately that's all we know about him so far and after this blog post he'll likely never date us.


  1. I think I might be four of those guys but we only dated once Jams, and we didn't even hook up. CHEATED!

  2. I can safely check 16 out of 20 off this list... and after all that, I was still able to snag the "good guy" who just happens to be "the one".

    Great post, Christine!

  3. he secretly wants to marry an athletic woman so that his kids will be good at sports.

    this is not a secret

  4. every part of that was awesome.

  5. Got the real estate guy down pretty damn well. - Real Estate Guy who knows other Real Estate Guys who also Bangs Cactus Club Waitresses and has a pad-locked blackberry.

  6. Minus the "He'll make sure you catch a glimpse of that $400 price tag" and "He takes his wedding ring off every Thursday night"... the Finance Guy sounds pretty damn decent wouldn't you agree? :)

  7. This is hilarious. And so unbelievably true. You girls are amazing.

    Just to top it off, I'd like to suggest the addition of #21, the filmmaker. Those of us who have lived in LA- or even vacationed there for ten minutes- will have interacted with this man at least once.

    The filmmaker is convinced that every single one of his ideas is brilliant. In fact, every one of them is so brilliant that he never shuts about them. Ever. He is convinced that as soon as Johnny Depp reads his script- thanks to his friend's uncle's assistant's dad who might be Depp's agent- Depp will drop the next remake of Pirates of the Caribbean to star in his film.

    Pros: This man knows how to hold a conversation- even if most of the conversation circles around himself. He is also great at gesturing with his hands, and has that messy hair thing down just about right. He could also- thanks to his dad's uncle's nephew's cousin- potentially get you onto a red carpet for a film premiere. So what if it's for a made for TV flick starring Hilary Duff?

    Cons: He will never really be focused on you because he's too focused on his unmade movies. He will be uber concentrated on you when you first meet him, promise to call you with a long intense gaze into your eyes and a firm squeeze of your hand, and then forgot about you by the time he gets home- to the point where the next time you see him, he won't even recognize you. Oh, he's also really great at hypothesizing about what it means to be a good person. Right.

  8. Very well done! And oh so accurate too.

  9. Loved this blog Bella!
    Nailed it!
    Thanks for the ab workout!