I’m going on a date this Friday night. And I need ideas.
Why do I need ideas?
I need to break the standard “date model” with this woman and I am having a hard time figuring out how to do that without comming off as “too much”, etc., while still keeping the date unique, fun, safe, casual, and (hopefully) sentimental.
And I’m new to Chicago.
Dinner would be a nice part of the evening, but not absolutely required. I’m looking for an activity. Something fun to do, followed up by light drinks afterwards.
I was thinking maybe indie theater or a comedy club. I have been to neither. Do any late evening ‘walking’ activities exist? Such as late-night art showings, museums, etc.?
I was almost thinking about a shared class, but that might be too soon. We’ve met up before, but this is our “official” first date. So, I need to do it right. We’re not strangers, but we need the opportunity to find out more about each other without burning ourselves out during the course of the evening.
If you can’t tell, I’m sort of stressing about this - not dating, but dating her.
If you want something offbeat, you might want to consider taking her for a carriage ride. Depending on how much you want to spend, they have 30 minute rides for $40 or 60 minute rides for $80; a bit pricey, perhaps, for a “first date” but sure to make an impression if that’s what you want to do. Don’t forget to tip the driver.
If you don’t mind staying up late, take her to see Too Much Light Makes the Baby Go Blind. For drinks afterwards, you can’t beat the Hopleaf for beer selections (though admittedly their liquor selection is lacking, if in fact it exists at all.)
What it really sounds like you want to do is take her to the Art Walks (second Friday of every month) or the Annual Artist’s Open House (end of September) that happen in the Arts District/Pilsen. Unfortunately, neither is happening this weekend.
I think the carriage ride is a bit much for a first date.
And, yes, BYOBs abound here in Chicago. I find Tanoshii quite fun. While I tend to be a nigiri kind of guy, this place really is about the rolls, and Chef Mike does a fantastic job with them. The atmosphere is fun and relaxed, pretty ideal for a first date, IMHO.
But Chicago has BYOB Mexican, BYOB Barbecue, BYOB Thai, etc…There’s a good number of no-corkage fee BYOBs here in the city. Here’s a list of 501 BYOBs in the Chicago area.
Anyhow, I second MikeS’s suggestion of Too Much Light… followed by the Hopleaf (although Hopleaf can get a bit overbearingly crowded.)
Here’s another one: those Architectural Chicago River boat tours are actually a lot more interesting and fun than you might imagine. It’s one of those things I always dismissed as just something tourists do until I actually took a visitor along on them. They’re informative and the perspective of the city from the Chicago River is unique and eye-opening. It definitely gets a thumbs-up from me.
Also, Millennium Plaza has free concerts throughout the season. Grab a picnic lunch/dinner, a bottle of wine (alcohol is permitted at Pritzker Pavillion), and a blanket, and enjoy the music, scenery, and conversation.
Crap. It looks like the concerts in the park ended last week. However, re-reading your OP, the suggestion might not have worked for you, anyway. When you say “Friday night,” what time are you looking at?
Another interesting idea, if you think this is her thing, is the Chicago Ghost Tour. You learn a bit of history, and might even see some ghosts: http://www.chicagohauntings.com/schedule.html
I also second the architecture cruises as a good date idea. There’s also cruises that go out into the Lake that give you great views of the skyline, without necessarily being about the architecture.
Just hanging out at Navy Pier at night is a fun time. The Stained Glass Museum there is definitely off-beat, and there’s usually a band playing somewhere, and lots of options for food and beverages. Not to mention people-watching, boat rides, and shopping.
Still no idea where Yesterdog went. But at least now I know where to go if I want to go on a date with someone whose career objective is camp counselor or college R.A.
Just to note: Yesterdog started this thread back in August 2010, so that date is done and gone. The thread was revived by **Nifty[b/] a few days ago. Welcome to the Straight Dope Message Boards, Nifty; we tend to call such a thing a “zombie” thread (i.e., resurrected from the dust and ashes). There’s no problem with doing it, per se, but we do have people reading and not noticing the dates on the posts, thinking they’re offering great current advice. The “desparate” in the thread title is thus somewhat… um… anachronistic.
Although, in one sense, “what to do on a date in Chicago” is timeless… In a more practical sense, some of the venues suggested may no longer exist. Consequently, I’m warning people to be very careful about making plans based on two-year old suggestions: check first.