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The (hopefully, possibly, maybe) first date

Your hot-as-hell coworker asks if you want to grab a postwork drink. You're hoping it's a date, but who can tell? Play your cards right and you could take this office friendship to the next level.

By Ruth Welte
Photo: Martha Williams

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Whether it’s a date or not, an art exhibit will give you plenty to talk about (goodbye, awkward silences). Tell her you’ve been planning to check out the current free art exhibit at the Chicago Cultural Center (78 E Washington St, 312-744-6630). That sounds like something you could do with a bud, right? If, on the way out, you remember that you also wanted to look at the gorgeously rehabbed Tiffany art-glass dome on the third floor, that’s just a coincidence. A really romantic coincidence.

Going poorly

Going well

 

The first date | The meet-the-parents date | The get-me-out-of-the-doghouse date | The cheap weekday date | The under-the-radar, underground date | The solo date | The true bromance/girlfriends date | The special-occasion date

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September 15, 2009
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