Ways to Avoid Fifty First Dates and Nail the First One

I asked a guy out. Yep, I’m a modern woman. I’d love some creative date ideas, that don’t involve picnicking. Thanks, Tessa.

bikes, beers, and an alley. you're all set.

bikes, beers, and an alley. you’re all set.

Dear Tessa,

I love dates. I love dates the same way I used to like pop quizzes and presentations in school; there’s something about the anticipation and the ceremony of it. In my experience (tests, dates, whatever), elements of mystery and ad libitum make everything more interesting.

Now, everybody knows a guy. I’m talking about that guy that can’t possibly be employed, but somehow finds the means to patronize every new culinary destination in town that’s been open no more than a week. Enigma that he is, this is why you keep track of him, even through every contact transfer from every outdated (read: destroyed) cell phone you’ve had since college. So, first recommendation? If you want to surprise your unwitting (though quite willing) prospect with a trek down an alley littered with mixologists in suspenders to a secret Korean BBQ lagoon, make that call and you will accomplish dating feat number 1: intrigue.

From there, a few things are key to the success of an evening born in adventure, so just pick one thread and pull. Don’t worry about curating the experience. Take a hail Mary leap of faith, then follow the coattails and golden pocket watch down the hole-in-the-wall to a steaming pot of lapin au vin. Otherwise it starts to feel contrived and desperate. You want to make an impression, but still enjoy the ride because at the end of the day, all that matters is that everyone had a good time. Not where you went.

Try to pinpoint your dates happy place between daring and comfortable. Unless your plans involve fireworks, bigger = better is not the golden rule. Don’t take the guy you met at Saddle Ranch over a couple steins of domestic lager and charred, bourbon BBQ’d animals to the vegan Indian food restaurant your sisters yoga instructor referred you to. Science, speculation and hearsay has proven that people who go through traumatic experiences together bond more quickly and deeply (which is why on the next date he’ll try and take you to a horror movie). You want to boldly set sail into uncharted waters together, but you don’t want mutiny on your hands.

Adventure dates are always my favorite because they’re fueled by mutual optimism and devoid of expectation. If it’s a success, you relish in the triumph of your team effort. If it flops then there’s no one to blame except luck and bad references, and you have a good excuse to buy each other another drink and get creative. Also, a commitment to the unknown is a good indication of how someone feels about you. The guy who will come salsa dancing with you despite two very large left feet is guaranteed to be genuinely interested in spending time with you, regardless of the setting.

Good luck and Godspeed, and remember: practice safe eating – always use condiments.– Chris Brown

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