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  • Features

    Time Out Chicago / Issue 154 : Feb 7–13, 2008
    The dating issue

    Date our friends

    We can’t believe they’re still single, so hook up with our hottest, smartest, funniest pals before they’re taken. Then follow the progress of their dates all throughout February.

    By Jason A. Heidemann
    Photographs by Lindsay Gallup


    Date Lisa: When not running a small nonprofit, she’s listening to Cat Power, watching indie films, and matching you drink-for-drink at the bar.

    Meet Lisa’s date: Deron isn’t above using a picture of adorable little kids or a mix tape to score a night out with Lisa.


    Watch Lisa’s date: Lisa and Deron swap bowling for darts at Lincoln Square Lanes.


    After Lisa's date: Lisa writes us a "Dear John" letter


    Date Todd: His perfect match? Anderson Cooper-meets-Paul-Rudd. But if you’re a guy with an artsy side and a love of cheeseburgers, that’ll do just fine.

    Meet Todd’s date: This fashion agency director lives the high life, and drinks it.


    Watch Todd’s date: Todd and David take in an afternoon at the Garfield Park Conservatory.


    After Todd's date: Todd says there's more in store for him and David


    Date Dawn: She loves traveling, caffeine, dogs and break-dancing. While you are wasting time reading this sentence, a hundred other dudes are already e-mailing her.

    Meet Dawn’s date: A funk DJ who appreciates beauty in nature and on the dance floor.


    Watch Dawn’s date: Dawn and Scott start their night at Juicy Wine Co.


    After Dawn's date: Did Dawn and Scott find a similar rhythm?


    Date Rob: A perfect gentleman who loves to cook, is wicked smart and has a jones for Britpop. Line forms to the left, ladies.

    Meet Rob’s date: A writer and yoga instructor, Sarah won't bend the truth to get a date with Rob.


    Watch Rob’s date: Rob and Sarah have a bowl at Lucky Strike.


    After Rob's date: Rob thanks TOC for the Date Our Friends experience




    Visit this page as we post more video clips of our friends' first dates, and vote on whether they’ll make it to the second.






    • Comments
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    • 4152 Jeff Tue, Mar 04, at 11:29pm
      Not sure who was responsible for picking a date for Lisa, but gosh, unless the pool was really small and the other candidates pretty ho-hum, I think you could have done much better... Deron referred to his friend's kids as "cute SOB's". Really? You would recommend this guy as a date for your girlfriend? I watched the video. Yikes! Poor Lisa.

      Flag as inappropriate


    • 3675 Meg Fri, Feb 15, at 03:44pm
      you and rob should date!!!

      Flag as inappropriate




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