Occupation: Public Relations (and part-time Socialite)
Neighborhood: River North, Gold Coast
Alma mater: Miami University – Ohio
Molly is a stunner, whose got everything going for her. And you might be inclined to be intimidated by her at first. Until you find out everything from her over-the-top apartment to her cleavage, were all paid for by Daddy’s credit card. (Ain’t no shame hun, most would if they could.) Aside from endlessly talking about all the C- local celebrities she knows through work, she will promise to hook you up with all the latest, greatest “next” things in fashion and beauty, where she showcases them for fun at her second job as a socialite. Enjoy having mildly interesting conversations about absolutely nothing. But at least it’ll be at the hottest clubs where she knows all the bouncers but expects you to pay for the bottle service.
Occupation: Something important in Finance or Medicine
Neighborhood: The Loop or Streeterville
Alma mater: University of Chicago or an Ivy League
Rebecca, who graduated summa cum laude and only seeks out the crème de la crème of society, might lead you to believe you’re special because she chose to give you her time of day. But don’t be fooled by her very vanilla, opportunistic, “let me tell you about my time in the south of France,” aroma. She actually can’t put together a few sentences where she is not the subject of conversation. Although you’ll be tempted to jump off the closest ledge while talking endlessly about how she mastered everything in the Encyclopedia Britannica by age 8, think of the possibility of making it rain with her trust fund; and just keep nodding and smiling at the overpriced rooftop bar you’re probably at.
Occupation: Sports Marketing, Tech, or any male-dominated field
Neighborhood: Wriggleyville a.k.a BRO-VILLE
Alma mater: University of Iowa or Ohio State or just about any state school really
“Who wants a beer?!” is Ashley’s favorite phrase. And when she’s not shot-gunning those babies down, she’s high-fiving everybody right before the college game comes on. Ashley is not like other girls you know, she REALLY isn’t. She’s the guy’s girl because girls are so much drama and she’s just one of the dudes and they’re all her boys, and she’s like their sister. And if you ever run out of things to talk about, ask her to tell you more about what it’s like being the only girl in her department. On the upside, it doesn’t take much to impress Ashley – take her to the nearest Buffalo Wild Wings and bring all your boys with you. She won’t mind.
Occupation: Nurse or Health Clinician
Neighborhood: Bucktown or Lakeview
Alma mater: Northwestern
Jessica seems like a really sweet, down to earth girl who hails from the suburbs of Chicago. But don’t remind of her roots lest you get into a public argument about where the city of Chicago really does, and does not end. Because behind the sweet demeanor is an I-will-stalk-the-living-daylights-out-of-you crazy girl waiting to come out. Be sure to always meet her at the planned location, and do not invite her to your apartment at any point in the short encounter you two are certain to have. And definitely do not introduce her to your friends who she will follow online like a private detective. That is of course, when they are not mysteriously bumping into her long after the few dates you could stomach her, have long past. Might just want to get a restraining order.
Occupation: Social Worker, Teacher, or Professional Student
Neighborhood: The West Loop or Humboldt Park
Alma mater: A small private university in the Midwest or Loyola Chicago
Kristen who is the human personification of a social justice warrior is only interested in one thing: saving the entire world from self-destruction. Initially you will find her passion for doing good on earth inviting, like a modern-day Mother Theresa of sorts. But when she insists that your first date be at a late-afternoon soup-kitchen on a Wednesday in the middle of a snowstorm, you’ll start thinking twice about what you’ve got yourself into. If at all you can make it through endless rants about everything that is wrong with the world, do not add her on Facebook, lest you be suffocated with one charitable event another. Oh, and always ask Kristen first if it’s okay that you pay because her feminist rants are never too far from you reaching for your wallet.
Occupation: Lawyer, High-Profile Marketer, or some type of Funemployment
Neighborhood: Lincoln Park or Old Town a.k.a Yuppie City
Alma mater: Notre Dame or a large private University in the Midwest
Michelle is everything in a future spouse you would want. If you’re the type of guy who has ever dreamed about getting together with a future Stepford Wife, that is. While her favorite things to do are look for 10ks to run in and try out new work out routines, she doesn’t feel more herself than when she’s sitting with “the girls” on a Sunday morning, piecing together the weekend, and judging all the people they ran into the night before, while downing their bottomless brunch. After your first three dates, she’ll probably link you to her Pinterest profile or as she calls it, her “vision board” which will include an engagement ring that would take you 6 months to buy. Just enough time to get back to your senses and take to your heels. And if not, well, we’ll give you 3 years max before you move to the nearest suburb.
Occupation: Graphic Designer, Creative, Barista
Neighborhood: Wicker Park
Alma mater: De Paul, School of the Art institute, Columbia College
Danielle is a free-spirited girl with a weirdness that makes Bjork look tame, yet still has a Laga Gaga feel of trying way too hard. Her hobbies include doing whatever her craft is, completely naked, drinking PBR, and smoking just enough weed for you to ponder if this is really a “recreational habit” or a cry for help. If you’re not a biker, her new purpose in life will be to convert you to one, while teaching you all the best places to get coffee, tea, and vegan cuisine in the city. And if the conversation about how she got her first tattoo runs dry on your second date, you can always talk about how she needs to move to Portland. A move that would suit her (and probably you) perfectly, in the long-run.