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It’s not exactly Paris in springtime – okay, it’s the polar opposite (get it? Polar opposite) – but if you’re going to be spending February 14th in Chicago, there is a place for you to get your V-day party on. Here is a handy guide for every potential state of mind (or heart) on the most infamous of gushy days:

“I’m Alone, and I’m Totally Okay With It.” Proceed to spend your day as you would any other Friday in Chicago: Head to the Tin Lizzie to see the turtle races (yep, that’s exactly what it sounds like – place your bets, people), get your sophistication station on at Drumbar, or heck, stay home and watch Downton Abbey. God knows their love lives have more issues than yours.

“I’M ALONE, AND I’M TOTALLY OKAY WITH IT, OKAY?!” Who needs sentimentality when you’ve got shots? Drink beer as bitter as your outlook at the annual Screw Cupid Bar Crawl, starting at Durkin’s Tavern at 7 pm February 14th. The price of a ticket includes transportation between bars, food, and Cupid punch. One night stand not included.

“I’m Casually Dating This Person, So I Don’t Want to Do Anything Toooo Romantic.” Nothing says “No pressure” like mixing love and stand-up…or maybe that’s not true. But you and your significant other of two months/two weeks/two minutes can have a hilarious time at My Chicago Valentine, which is alternatively a send-up and a celebration of Valentine’s Day. It involves rap, pirates, and baseball – what more do you need? Well, maybe a shot from the theater’s bar. Now sit back, relax, and totally judge your date based on how much they laugh.

“I’m Totally in Love and Want to Sap-ify the Crap Out of This Holiday.” Check out TimeOut Chicago’s list of “10 Romantic Restaurants For Valentine’s Day” – they’re actually not some of the most famous names in Chicago, which is a pleasant surprise. Afterwards, of course, you can go ice skating in Millennium Park, read each other love poems, blah blah blah. Now stop making the rest of us feel bad.

“I’m Going to Propose!!” This is not a one-size-fits all sort of category. The website Love This City will help you get off to a good start, but the best proposals are tailored to the relationship. So do some research and get creative, you lazy bum.

That’s said with love, of course.



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