Somehow, I am the first person that people call when they have a date. Often times, the call is from a girlfriend but sometimes guys ask too. On a personal note, I don’t know whether I should be flattered (maybe they think I’m a cultured nightlife enthusiast who appreciates all the city has to offer) or insulted (because they think I eat out too much or have been on way too many dates.)
The call is always the same. “I have a date. “Where should we goooo?” Their voices exude both excitement and dread.
I usually ask a few questions like “Which date is it?” and “What kind of person is the lucky guy?”
Unfortunately, winter time in Chicago doesn’t offer a lot in the way of creativity, but that doesn’t mean you are limited to a night at the Cheesecake Factory.
Stick to some of the ideas below and you’ll have fun, even if there’s not a love connection.
Even if you think that you might really like this person, it is better to have a casual first date. You want there to be an adequate amount of activity, in case the guy is a dud. Conversely, if the chemistry is right, an environment conducive to conversation is ideal.
- A Bulls or Blackhawks game is a great idea, particularly if both parties appreciate sports. This is kind of a no brainer because most men are sports fans.
- Ice skating at Millenium Park. This is fun because you are likely asking him to go outside of his comfort zone. Watch his behavior; if he is a fumbling idiot, but is able to laugh at himself, then he has earned himself a second date!
- Walk through the Art Institute of Chicago on Thursday night – it’s free and open until 8 p.m!
11 S. Michigan Avenue
- Take a trip to the Chicago Cultural Center, which is not only one of the most impressive buildings in the city, but also a home to film festivals (March 6 – 8), poetry readings, art exhibitions and cultural celebrations.
78 E. Washington Street
Not The First Date...
If you’ve survived the awkward first date –hooray! -- and are ready for more datey activities, then keep reading.
- Webster’s Wine Bar – has to be one of the most charming spots in the city. This dimly lit hangout boasts an impressive list of wines by the glass – It is the perfect date spot.
1480 W. Webster Ave
- Tango Sur – This Southport haunt never disappoints. The BYOB spot features traditional Argentinean steaks with chimichurri sauce. The tango music is barely audible over the hordes of people – they don’t take reservations but the wait is always worth it.
3763 N Southport Ave
- Firefly – is a quaint, Boystown French bistro. The food is marvelous and it’s easy to get cozy and stay for a few hours.
3335 N. Halsted St.