Three lessons from a Chicago Singles Meetup

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Single City is a twice-weekly blog about the Chicago dating scene written by Sun-Times Media Wire reporter Sally Ho. Got a question? Email her!

In high school, clubs existed to make a big place feel smaller, feed your interest, keep you busy and let you meet people with whom you might not otherwise cross paths.

For the modern adult, Meetup.com recreates those little communities we never appreciated in school (shout-outs to my former debate team and Spanish club). And, as I recently discovered, it serves as the perfect (and free!) place to meet other singles.

Whether you are generically single or looking for a more specific crowd (such as lesbians, Christians or African-Americans), Meetup’s got it all. The catch-all “Chicago Singles” group alone has 750 members and hosts an event at least once a month, including wine tastings, parties, and even professional matchmakers.

I attended a recent Meetup at NV Penthouse Lounge, which included a free first drink, no cover, pretty views of the skyline and around 100 singles.

Here are 3 things I noted:

  • Do not attend these things alone. I saw several people going solo, which I guess makes sense since it is a “singles event.” But treating it like one only highlights awkwardness. It’s best to just relax like you would at the bar and bring an equally single friend. I brought my best research assistant/girlfriend.
  • It’s the biggest mixed bag you’ll ever encounter. You’ll literally find people of all ages, colors, shapes and sizes — some you are attracted to and others not so much. Dating is always a crapshoot, so don’t expect a singles event to magically conjure up a room full of the men or women of your dreams.
  • Take advantage of the venue. I usually frequent dive bars, so this fancy rooftop “lounge” was definitely out of my comfort zone — but because it was free, there was no harm in trying it out. The beautiful view and expensive drinks may not have convinced me of the merits of a dress code and a cover charge (except maybe at Carol’s Pub for the live country music on Saturdays), but it was worthwhile to experience the scene for a night.
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