Play it cool

Congratulations: You scored a first date with your latest crush. The outfit and post-date seduction scene are all planned out. Now, where to go? Think of dating like real estate--location, location, location. We've got the top picks to increase your cool quotient by taking your date somewhere that suits his or her personality.

So, you're dating a…

Hipster art student
Your date has an asymmetrical haircut, wears skinny jeans and is halfway through an MFA at the Art Institute. Don't take her to McFadden's; the Gold Coast address and Irish pub-chain vibe will hardly get you a second date, let alone to second base. Instead, head to the hipster art student hangout du jour, The Continental. Join the local Ukie Village and Humboldt Park crowd for a few rounds of PBR, then take your date home and show her your video art installation.

Organic hippie
He was taking in Devendra Banhart when you struck up a conversation at Pitchfork. He may be a tad crunchy, but he's super cute. Don't scare him off with thoughts of Reagan era excess at '80s-themed nightclub RadioStar. Instead, grab a table at Karyn's Cooked and treat him to an organic beer or wine. Who knows where it'll lead? You could end up planning a trip to the Burning Man Festival over a bottle of Scarecrow Organic Pale Ale ($6) or a glass of Citizen Cabernet ($9).

That girl who passed you her digits at the neighborhood fest looks young enough to be your daughter. Stay away from the Botox-ed, tanorexic crowd at Viagra Triangle spots like Gibsons, and go somewhere she'll feel comfortable. Try Mad River Bar & Grille: The new spot with a ski lodge atmosphere caters to young Lincoln Park professionals and nearby college kids. Just remember to grab a table in a dim corner so your date can't see your crow's feet.

Stock trader
You said yes to a blind date with a friend of a friend, and you just found out he's a trader. Steer clear of the usual suspect, Cactus Bar & Grill, unless you want to bump into his random hook-ups and past office trysts. Instead, book a table at luxe "Liquor Spa" Stone Lotus and order bottle service, which comes with an array of housemade mixers and nibbles crafted by chef and mixologist Dale Levitski. After all, your date can afford it after his last stock took off. But you better make sure he's paying.

Wannabe revolutionary
You always fall for edgy types with a social conscience. The latest? A wannabe revolutionary with a closet full of Che Guevara T-shirts. The last place you should choose for your date is Reserve; the opulence at this high-end lounge will be a clear turn-off to this fighter-for-the-common-people. Hyde Park's Woodlawn Tap may be more his speed. The low-key neighborhood bar draws a wide range of locals--including firefighters, construction workers and University of Chicago professors and students--for passionate discussions on everything from Marxist theory to Milton Friedman and, of course, pints of beer.

[Heidi Moore is a metromix special contributor.]
metromix@tribune.comOriginally published August 10, 2006.

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