Paris Club
There is no gentle, Mom-approved way to say this. Paris Club is where the pretty people go. Fess up, you've sipped your Gin Gin while simultaneously ogling the adorable trader, investment banker, or server stacking the deck at this River North hangout. Get a blowout, get a mani, get fancy, huh? This is the place to do it.
Paris Club, 59 West Hubbard (at Clark Street); 312-595-0800.
Rivers
Pay attention, because this one comes with specifics. Rivers is a riverfront restaurant with an interior suitable for meeting your boss, or perhaps your parents, for a nice meal. Don't do that. We want you to take it outside. Rivers is the best post-work spot in the city. Every summer weeknight, workerbees from the Loop congregate on a massive patio to enjoy drink specials and eye candy—lots of eye candy. Happy hour indeed.
Rivers Restaurant, 30 South Wacker Drive (at Monroe Street); 312-559-1515.
Whole Foods
Couples and families engage in weekend grocery shopping trips that make the March of the Penguins look like a walk around the block. Singles, however, take to the aisles on weeknights, when the milk goes bad, the cereal is stale, and the yogurt runs out. We don't know why we feel sexier among roasted pine nuts and gluten free pancake mix, but we do. Whole Foods is prime babe-watching for any Chicago single bored with the same, old routine. Without the typical boozy bravery a bar scene might give you, you'll have to try a little harder to drum up your courage, but we think it's worth it.
Whole Foods, 1550 North Kingsbury Street (just South of North Avenue); 312-587-0648.
Filter Cafe
We all know we shouldn't date in the workplace, but if you freelance, that pretty much means you can't date anyone anywhere, and that sort of blows. Snuggle up to your laptop at Filter Cafe, Wicker Park's premier hangout for freelancers of all kinds. A simple "is this outlet taken," or "what kind of tea is that?" can get a convo going in no time. That graphic designer with the Chuck Taylors and Colin Farrell eyes isn't going to ask himself out, is he?
Filter Cafe, 1373 North Milwaukee Avenue; 773-904-7819.
The Metro
Certain events lend themselves to traveling as a romantic couple. Two single dudes, for example, aren't exactly going to enjoy a dimly-lit dinner at Maude's Liquor Bar, we're sorry to say. There is however one event where singletons will travel in packs without even the slightest reservation—the rock show. Be smart about it, obvi. Pick a good indie rock band, run it by your best friend's boyfriend if need be. Then buy an overpriced beer, claim your spot, and gently peruse the crowd as the lead singer honeys up to the audience with witty banter. In-between-set trips to the bar are prime chat opportunities.
The Metro, 3730 North Clark Street (at Waveland Avenue); 773-549-4140.
Fireside Bowl
Again, non-romantic group activities usually mean two things: single people and booze. If that ain't a recipe for a single person's good time, we don't know what is. Pick any bowling alley you like, but we love Fireside. There is something cozy and very Chicago about this one, and we love the bar. Very Cheers. Roll deep with your same-sex pals and knock 'em dead. For the true ballers, we suggest looking into a bowling league. Seriously. Fireside Bowl, 2646 West Fullerton (at Talman Street); 773-486-2700.