A table for two is ready for you and your hip date at Edgewater Lounge.
I've dated my fair share of boys in tight jeans and ironic t-shirts. Half of them were musicians, the others tortured writers and professional baristas. These dates never went very far (you can only date a guy who looks better than you in women's pants for so long), but some of the regular haunts we visited were relationship-worthy. Here were my favorites:
The Flat Iron
My visits to Flat Iron have always been early in the evening, when the crowd is sparse. It's a great opportunity to really check out the artwork painted on the pub's walls, when herds of trendsetters aren't leaning against them. The century-old building, which functioned as an art colony in the 1980s (and The Note until last summer), houses work from ten local artists. So it isn't any surprise to find a myriad of creative types holing up in the place. And let's not forget, you're still in Wicker Park, where hipster love is always in the air. In the event that you and your date hit it off here, head next door to Debonair Social Club and take things to the next level with DJs and dancing. Should you need to refuel, Flat Iron stays open until 4 a.m.
Inner Town Pub
You may not be able to smoke inside, but Innertown Pub is one of the few spots left sporting a real-life cigarette machine. The bar's interiors resemble something of a shipwreck, as if maybe the Titanic sunk here. But instead of sapphires and fancy dresses, you'll find baubles, bumper stickers and beer signs. Reveling in all the kitsch and PBR, are a number of local hipsters sporting discerning looks. It's easy to feel unwelcome when weaving through these tables of regulars, but as long as you can name five bands no one's ever heard of, you'll pass unscathed.
Located just down the street from Inner Town Pub is a joint that's sure to make you smile. Perhaps that's where it gets its cheerful moniker. Because of its discreet locale, you wouldn't expect much of a crowd here, but Happy Village packs in a full house on popular pub nights. It's a great spot to hit in the summer, when the massive back patio opens to reveal a replica of what your backyard might look like during a family reunion, minus the nagging kinfolk. Large garden tents provide shelter from the sun and strands of faux ivy strung with lights add a kitschy charm.
Sitting unassumingly on the corner of Ashland and Bryn Mawr, Edgewater Lounge appeals to a loyal crowd; it relies on regulars, as the place is easy to pass thanks to its stark, paneled exterior and long-faded sign. This pub is not one that prides itself on classic mixed libations, but Edgewater Lounge does sit high on its select brews. Stained glass windows and high-back wooden booths create the perfect back room for cooing and canoodling, while the front room caters to singles parked at the bar.
Small Bar (Logan Square)
It's one of the few spots in Logan Square that doesn't spill into Bucktown and still reels in an American Apparel-clad crowd. The beer selection is shocking (read: good), given the pub's location, but the crew's discerning taste shines through with its brews and late-night menu. I always bring an appetite to this place, as it's one of the rare spots where I've had healthful (and flavorful) pub fare (try the homemade hummus with pita wedges). A heated patio provides shelter for those stragglers who came too late to snag a seat at the bar and a corner television streams sports for those who can't miss a beat.