How to conquer first-date planning


As the self-proclaimed president of the Forever Alone Society, I have had my fair share of kissing my mom at midnight on New Year’s and organizing singles-only Valentine’s Day sleepover parties, where I wake up alone with obscene things drawn on my face and the menu screen of “Bring It On” playing in the background. So when a sexy Scottish fitness trainer (let’s call him “Braveheart”) asked me out for coffee, I took full advantage and planned a date that was unlike any he’d ever been on, which sparked this new summer dating series.


I decided to take on the new journalistic project of experimenting with various date ideas and chronicling these misadventures in an article. It is my fondest hope that you ditch your drab movie-and-dinner date plans and opt for an outing that has a second-date guarantee.


As a brave dater myself, and with my previous amateur competitive eating experience, I decided to take Braveheart to watch me tackle the Hellfire Challenge at the SmokeEaters wing bar in Cupertino: 12 hot wings coated in black inferno hot sauce in 10 minutes without water or napkins. You do need to sign a waiver releasing all your legal rights to sue the restaurant for any unexpected bleeding of orifices or accidental contamination of your eyes with the sauce, but it is definitely worth it for an extra-large victory T-shirt.


Unfortunately, after a wing and a bite of Hellfire, I started bawling in a restaurant full of spectators who laughed at my defeat and then resumed watching La Liga on the high-definition TVs. However, this is the perfect opportunity for brave date-goers to lick hot sauce off each other’s fingers and experience a hot summer night unknown to the likes of Northern California. Braveheart received extra points for bringing me a lifetime’s supply of Pepto Bismol and running to the nearest convenience store for milk.


The perfect follow-up to the hot-and-heavy Hellfire Challenge is a cool-down nighttime swim at Half Moon Bay. The journey, a mere 45-minute drive from Cupertino, provides a romantic interlude for a million conversations to unfold. Listen to Frank Ocean’s sweet crooning on his new album “channel ORANGE” and let the serenade set an atmosphere for the late night. On the walk down to the beach, it is essential that you guide your date down the rocky pathway and take the opportunity to hold her hand. I offered Braveheart a piggyback ride and won him over with my bravado. If you’re feeling particularly adventurous, go skinny-dipping and reenact that honeymoon scene in “Breaking Dawn.” Afterward, keep each other warm on the beach with proximity and conversation. Be kind to each other; the NorCal summer nights are Siberia brutal.


It’s the formula for a winning first date and a guaranteed second. Braveheart is already planning our next outing.

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