Volunteering may fall low on your summer priority list, with the day drinking and the beach-going, but as a non-bar way to meet people, it's top notch. Plus, you get to support a cause you care about AND meet cute people who share a common interest. I'd suggest you go walk a dog at New Leash On Life or lend a hand at one of its adoption events. Playing with puppies is not just good for your love life, it's good for your mental health. For other outdoorsy opportunities, like mural painting or teaching at-risk youth how to avoid getting poison oak, check out Volunteer Match.
Bars with outdoor seating are an obvious and plentiful choice for hookups. I could no sooner choose a favorite than I could choose a favorite star from the heavens. Except, fine, it's Phyllis' Musical Inn. Onward!
There are TONS of street fests, neighborhood fests, food fests and music fests every weekend. Obviously the bigger ones like Taste of Chicago and Lollapalooza will be packed with people, and those kinds of crowds can be intimidating and rage-inducing. It is, however, really easy to start a conversation with a stranger at such events: "What do you think of this band/delicious meat-on-a-stick thing?" I'd also suggest keeping an ear out for when your neighborhood is throwing its fest, so you and the friendly neighbor you just met won't have to stumble more than a few blocks home. Go earlier in the day if you want to avoid the really garrulous drunks (and lobster tans). And you'd be remiss if you didn't check out the stellar free music and movies in Millennium Park. Who doesn't want to get durrty after watching "Pee Wee's Big Adventure?" No one.
What better way to flirt with a stranger than to mercilessly trash talk them during beach volleyball, softball, kickball, flag football, etc.? Cue organized sports leagues like Chicago Sport and Social Club. CSSC has both competitive and recreational teams, for those who aren't in it to win it (at least in thatway). Plus, you don't need a bunch of friends on board to make it happen. You can do this shizz solo or, if you need to, with a wingman or two. Either way, you'll meet lots of new people, burn some of those beer calories, and maybe even develop appreciation for other kinds of balls.
Sports (for lazy people)
If your preferred exercise involves only your arm and your mouth hole, then get thee to a Cubs game already. But before you do, download the OkCupid, Grindr (if you're a dude into dudes), or Blendr (if you're into everything else) app on your smartphone. These apps sync your dating profile with GPS so that you can meet and vet people nearby. If you see someone on the app you want to see naked, then you can message them a little before deciding to meet up at the hot dog cart. Be sure to use lots of baseball terminology in your messages, not only because it's relevant, but because it's brimming with innuendo. Play your cards right, and you'll be rounding third base in no time.
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