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Make the most of summer dating in Chicago

OPINION

(Zbigniew Bzdak/Chicago…)
June 06, 2013|By Annie Reed, @annie_e_313 | For RedEye

Now that it's (almost) officially summer, we should talk about how to date in these precious balmy months—because let's face it, they fly by and we can't afford to waste a hot minute on a bad date.

If you have a significant other during the Chicago summer, you must really love each other because the unofficial rule is that come June 1, it's time to get single again. Nesting season resumes in October.

Whether you're single or you're new to Chicago and just looking meet new friends (or both), you're probably on an online dating/meetup site. Me too! Here are a few do's and don'ts from my experience to help make the most of dating during this swinging single summer.

Do: Host group barbecues

Don't get me wrong—I love grilling with my friends and roommates. I do it like three times a week. But sometimes you want the excitement that comes with inviting total strangers to your house to blaze meats and guzzle beers. As my stated goal on OkCupid is to find friends foremost, I have taken to sending mass invites to like-minded OKC ladies whenever I'm hosting a BBQ. The upside is you are never trapped in a formal bad first date. The downside is the invitees may hook up with each other instead of you. But it's hardly a downside as long as you are drinking beers with good—albeit random—company under the Chicago sun.

Don't: Schedule first dates on weekends

Weekends are the precious gems of summer. I learned recently that it's not worth risking them on a first date. Sure, Saturday brunch followed by an afternoon of urban exploring sounds like a great idea. But when you get to brunch and realize all of her interests are the bane of your existence, you know it's going to be a long day. And to think all your friends are throwing down at a street festival ...

Do: Schedule first dates on weeknights

Depending on your job, you might have up to three hours of sunlight left once you punch the clock for the day. That is a perfect window for first dates and meetups. With the right activity and the right time parameters, no date's a bad date (because really you are just dating the summer in Chicago).

Here's a few suggestions

Keep it simple

Meet for happy hour. Happy hour outside. Happy hour outside on a rooftop. Date sucks? Bam—happy hour ends at 6 and you've still got two hours of sunlight to bask in. It's going well? No one really knows when happy hour ends—and you're not actually going to that Pilates class at 7 p.m.

Keep it healthy

There are a fair number of running stores/meetups that hold weekly group jogs. If you guys both like jogging, y'know, you could do that.

Keep it classy

The best weeknight activity in Chicago—bar none—is Symphony in the Park. Starting next week, Every Wednesday from 6:30-8:15 p.m., the city of Chicago invites you to spread out a blanket, crack a bottle of wine and kick back while one of the best orchestras in the country serenades you under the setting sun in Millennium Park. It's free. It's all BYO. And you can talk through the concert if classical music isn't really your thing. It makes a great date no matter who you take.

Annie Reed is a RedEye special contributor.

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