Ask the Ex-Working Girl: Adjusting to Life Outside of NYC
By BankersBall on Jun 4, 2006 in Ask the Working Girl, Girlfriend!
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Hello.
I read your posts and find them to be entertaining and interesting. I’m a 25 year old hedge fund trader in Chicago and am really frustrated because I’m unable to meet women. The “hot” girls at clubs and bars are difficult to approach, and there are almost no females at my work. Moreover, I went to college in the East coast, so I have very few friends here. I feel like I’m in a hopeless situation. Is there anything I can do to rectify this? I’m planning on going to B-school eventually, which will allow me to meet more people. It’s just that I’m having a hard time fitting into the Chicago scene; I much prefer New York, but I’m forced to be here because I haven’t been able to get good job offers in NYC.
–Frustrated in Chicago
But here is what I surmise from your short email. You are a young, well educated and intelligent (they don’t always go hand in hand), successful chap. You’re in a new city and you want to meet some hot girls to have fun with. But you sound like you’re not a playa and a bit intimidated by hot girls in their home territory (hot clubs). So here is what I suggest. Instead of approaching hot girls in clubs and similar settings, how about building a network of cool guy friends at work that you can hang out with. You might get introduced to some of these guys’ gal-friends, who happen to be attractive. And furthermore, if you have couple guys that you can use as your wingmen when you’re at these clubs that will make it easier (1) to buy tables at these clubs and (2) invite hotties over to your table to have drinks with you. If you need further guidance on perhaps where to hang out in Chicago I can help with that too.
I happen to love Chicago and found the night life there surprisingly tolerable. I also have some hot girlfriends there who are i-bankers actually 
When I checked out the single scene there I personally loved how all the midwestern boys were so tall and wholesome looking.
As for meeting people in B-school: the chances of you finding a hot girl in B-school is slim to none. You do know that 3 out of 4 people in B-school are male? And of women, what percentage do you think would be hot and not attached to someone already? You’re a hedge fund trader, you do the math.
Good luck to you and maybe I’ll run into you at Japonais or Redofive in Chi-town.
P.S. Obrigado for finding my posts entertaining and interesting.
On Jun 5, 2006, Jack said:
You go to b-school to meet undergrads, silly.
On Jun 5, 2006, ex-working girl said:
Don’t know how old you are but the average age of people in b-school for the last 5 years have been 29. So if you think its cool for a guy in that age range to have to resort to spending 100k (not to mention opportunity costs to date girls 18-21 then no wonder you think you have to go to b-school to meet girls.
Personally I think the best reason to go to school is so that you can drink non-stop for two years with a legitimate excuse, silly.
On Jun 8, 2006, GCH said:
Sounds like your problem is that you have no self-confidence, not that you live in Chicago. Chicago has some of the best nightlife in the country, after New York and arguably LA.
If you’re intimidated by the Rush St. scene, try Lincoln Park. That’s a lower-key, post collegiate scene. If you can’t pick up a girl there solely on the basis of going to a East Coast school and making more than $100K, then you should probably quit life now.
On Jun 15, 2006, NJG said:
Rush Street is for meeting suburbanites and tourists from out of town. Lincoln Park is not much better, unless your frat or sorority was the best thing that ever happened to you. The Viagra Triangle, just south of Rush and Division, would probably be too intimidating as well.
Have you considered First Fridays at MCA?
On Jul 24, 2006, anon said:
Chicago is a big town, grow some b*lls and talk to these women with confidence! It’s not that hard…..