Occupation: Something important in Finance or Banking. Or whatever he’s doing, he’s making 6 figures.
Neighborhood: Hyde Park, Gold Coast, or River North a.k.a the residence of choice for the modern bourgeois.
Alma Mater: University of Chicago (AND currently taking post-grad classes at Booth Business School.)
Derek is a real winner ladies…on paper. But what he lacks in personality, he makes up for by talking endlessly about his stock options and the second condo he is going to buy next year. He’ll mention the fact that he went to University of Chicago at every opportunity, so brace yourself for pretending to care. But at least he’ll take you out for some fine dining where he’ll talk about all his other fine dining experiences! And if you get so bored by the end of the night you actually attempt to kiss him, be sure to explain the theory of kissing first. Why? Because knowing how it works in practice is not as good as knowing how it works in theory! (Am I right U of C grads?!)
Occupation: Accounting, Engineering, or Lawyer
Neighborhood: Lincoln Park, Lakeview, or Old Town a.k.a Yuppie-city!
Alma Mater: Notre Dame
William, who will insist that you indeed call him William, (because he is not Billy or Bill or Will or Willy as he will constantly reminding everyone), will proclaim that he’s just your regular nice Midwestern guy. And indeed this dude is so nice, you’re not actually sure if he wants to date you or adopt you as a pet. But the ladies will flock to him and so when he chooses you, it’ll feel like you’re something special. Except you’ll realize there’s no difference in his sweet-nothings to you and how he talks to his grandma, which just ends up being creepy and weird. And how do you spot a William, you might ask? Easy. He’ll tell you he went to Notre Dame before he’ll tell you his name.
Occupation: Finance, Tech, or Marketing
Neighborhood: Wrigleyville a.k.a BRO-VILLE
Alma Mater: Iowa, Michigan, Michigan State, Ohio State, or UW – Madison
Matt is just a really chill guy you know. HE’S JUST SO LAID BACK AND CHILL! Except when it comes to sports leagues, of which he’s enrolled in volleyball, basketball, softball, dodgeball, etc. from Monday to Friday. And when he’s not playing, he is watching ALL THE SPORTS. And you guessed it, he even played back in the day. But is he talking about his college PRs? No. This kid is still hung up on being part of his high school championship winning team. Try not to be too unimpressed when your first date involves him screaming GO CUBS GO (or whatever baseball team he’s into) at dinner because he sacrificed watching the game LIVE to take you out.
Occupation: Something Medicine-related, Computer-Science, Trader, or You’re not really sure but he’s not poor.
Neighborhood: The Loop, The West Loop, or Streeterville a.k.a Places for people whose favorite ice cream is “Vanilla.”
Alma Mater: Northwestern, An Ivy League, or other East Coast school that’s you know, “impressive.”
Bryan, who will go into a fit of rage should you ever misspell his name with an “i,” proudly wears the “douchebag” identity on his sleeve. The sad reality however, is that Bryan doesn’t actually have the balls to be a douchebag. And so he’s a walking comedy show who doesn’t know that everyone is laughing at his pretentiousness and not his jokes. Unsure whether Bryan just has the best-paying job on the planet for his experience, is a trust fund baby, or is simply swimming in debt, he insists on being that guy who sniggers as you reach for your purse to pay for something because he’s always got it. Not that you’re complaining. In fact, sometimes you think you could marry Bryan. But that’s always interrupted by the thought that he is also a spoilt, man-child. And you’d rather gouge your eyes out than listen to one of his unfunny stories, or the latest reason he thinks the East Coast is so much better than Chicago.
Occupation: Hipster, Bartender, Barista, Graphic Designer, (Sometimes a combo of one, two, three, or all four!) or he’s unemployed. :(
Neighborhood: Wicker Park, Humboldt Park, Logan Square or Edgewater a.k.a Anywhere there are hat-wearing, hard-core cyclists that brew their own beer.
Alma Mater: Columbia College Chicago, DePaul, or the School of the Art Institute
Calvin is actually a really interesting guy with big dreams and an even a bigger heart. He survives either on his parents dime doing what he loves or does indeed have a trillion jobs. In any case, your dates will probably consist of seeing him at one of his many jobs, and listening to his band play at some indie coffee shop. Or most likely, sitting on his couch watching Netflix with his five roommates. He’ll constantly talk about moving out to Portland or how he’d just love to pick a place in the world and never come back. And it’ll all sounds swell and romantic until you realize this dude doesn’t even have a passport. But at least he’ll always keep you hydrated with some gluten-free IPAs. Unless he’s going through unemployment currently, in which case his supply of PBR will still be limitless.
Occupation: Actuary, Pharmacy, IT
Neighborhood: Bucktown a.k.a. I have money and I want you to think I have good taste as well.
Alma Mater: A small, private university in the middle of nowhere. Or Loyola Chicago.
Zach is probably from the suburbs of Chicago or the suburbs of any Midwestern city although he will argue till the death that he really is from the city. But he gives himself away every Thursday at 25 cent wings and dollar beers night, at some dive bar that reminds him of his good ol’ college days. Still, prizing himself on working hard and playing hard, he’s not really the “dating type” which he will at least be upfront about from the start. So he’ll insist you two should just be friends. But he’s the kind of friend who will send Friday night booty- texts, Saturday morning apologies, Saturday night flirtations, Sunday morning apologies for Saturday night texts, with the promise to buy you brunch. (Tip: Zach doesn’t only want to be your friend but he’s still heart-broken from his college ex-girlfriend who still visits him from time to time.)
Neighborhood: Somewhere in Chicago where all his family have lived since the beginning of time.
Alma Mater: The school of hard knocks and/or University of Illinois-Chicago or University of Illinois-Champaign.
Jeff is a Chicago boy but unlike the other guys above, he is no “transplant” or “burbs pretender.” No, Jeff is a “real Chicago boy” who grew up in the city and would never dream of living elsewhere. Chances are, he lives amongst “his people” (insert whatever hyphen of foreign country with “American”) and he’ll constantly tell you how his grandmother will freak out when she finds out he’s not dating someone in said hyphenated community. Look forward to sensational (see: far-fetched) stories about growing up in Chicago and if you ever get lost in the city, he’ll insist that Google Maps has nothing on his memory because he knows this place like the back of his hand! And should you ever tell him he might be wrong about any of his Chicago knowledge, look forward to a snigger, a pity look, and a pat on the head while he insists your pretty little transplant head must be confused. And then of course, he’ll proceed to tell you yet another story about being a “real Chicago boy.”