The date ended the way it usually did — my car parked outside of a small soccer field in Cupertino, seats leaned all the way back and Adele crooning softly in the stereo.
Except it wasn’t a date.
It was another one of those daylong excursions with a friend I met at a res hall ice cream social. This day was the beginning of my three-part attempt to ask her out.
I’ve always been a spontaneous individual, the unaccountable variable, and asking out girls is no exception. My first ask ever was in a big mall next to kiddy rides while hanging out with friends. My second ask was in an open park next to the library as we were chilling under the shade of a giant tree. Both times I was shocked at myself, and so was the girl.
This time, I carefully constructed the perfect plan to woo said friend.
On the first day, I would take her around her hometown, among the homely and romantic annual display of festive lights at Downtown San Jose’s Christmas in the Park. I’d satisfy her frugal tastes with a three-in-one ticket that encompassed ice skating, the Tech Museum of Innovation and the San Jose Museum of Art. The next day we would go mini-golfing, filling in the cliché rom-com roles of the slightly clumsy girl in the arms of the swooning boy as he teaches her how to putt. The third and final day would involve a bowl of her favorite cereal and a drive-in movie theater. Hopefully, through this saga, I’d end up with a girlfriend.
The first day almost went as planned. Because her particular taste in art didn’t align with the art museum’s, we resolved to push it to the next day. Instead, we spent the day among little kids making parachutes and slipping on ice. We grabbed hot cocoa as I snapped a few adorable photos of her drinking cocoa, lips covered in whipped cream.
And this is where the plan started to crack. Fast-forward to the lounging in the car and Adele serenading through the speakers, and she asks me a question that throws me completely off guard: “Do you like anyone?”
This wasn’t part of the plan. I was supposed to ask her out on the third day. I didn’t know what to say. I stumbled and stammered and sputtered out, “No. It’s complicated.”
After she left the car, I slapped myself. It’s complicated, I thought. Literally one of the worst things I could say to her. Now she probably thinks I’m not interested in her. Come on, coach. Take a timeout. Stick to the plan. Take a few breaths. You still have two more planned days for this to work out. Give it time. You can do this.
The second day had some issues. I surprised her at her door — not with flowers, but with a guilty expression, having forgotten the discounted art museum tickets.
Then she got cold feet — because I dropped her in the freezing waters of Half Moon Bay. Instead of a lacking (by her standards) art exhibition, our day turned into a lighthearted photo shoot in the grainy sand and chilly winter breeze. And I still got to hold her arms and “teach” her mini-golf. Also, I scored more points than she did, though she might say otherwise.
The third day started eerily similar to the first: We had planned to eat her favorite cereal together in the morning, me supplying the bowls, spoon, and cereal, and her the milk.
Thirty minutes after I was supposed to arrive, I showed up at the door with two glasses of milk.
“Where the fuck’s the Cinnamon Toast Crunch?”
One Safeway run and breakfast at her house later, the most typical yet worst thing happened: I was assigned to write a Daily Cal news story.
She graciously lent me her high school’s library and Wi-Fi, and she patiently waited as I called UC Berkeley professors to respond to right-wing provocateur Milo Yiannopoulos’ planned February visit to campus.
That night for dessert, I took her to a high-end restaurant with a familiar, branded, golden “M.” Armed with a drive-through order of 20 piece Chicken McNuggets, I parked the car at the drive-in movie theater: meaning I had an 11-inch laptop, a parking spot outside of a Starbucks and a most-likely illegal streaming of “Ferris Bueller’s Day Off” that consistently buffered on the free Google Wi-Fi.
She swooned.
As Ferris Bueller turned his head toward the camera in the post-credits epilogue, his exasperated words “It’s over, go home” were seemingly directed toward me, and the words spilled out of my mouth.
“Will you go out with me?”
Despite all the planning and worrying, second-guessing and surprises, I asked her out the same way I always had. Spontaneously.
While my meticulous planning tried to mold the beginning of this relationship into one for the movies, like all the cliché rom-com plotlines, the unaccountable variables always ruin the plan. Although for them, it’s rain, lost numbers and missed buses, and for me, it’s Cinnamon Toast Crunch, forgotten tickets and the Daily Cal.
