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Blog #21: How to wing-woman for a guy who’s trying to get phone numbers (Me & Payton go out, pt 1)

Each post is a great fucking adventure

As Seen On
by in Sex & Dating
June 11, 2018 0 comments

Tonight is game night. Pick-up night. Shoot your shot night.

Um, you get the point. Payton and I are going to go out and find a bunch of people for him to hit on with the goal of practicing rejection. San Francisco is a small city. I’m only crossing my fingers I won’t run into a friend on the street.

I’ve just returned from rural Oregon. In-between travels, all I can find to wear is a dress with sleeves that are too long. Why do I own this? Fuck it. I’m putting on some lipstick from an unused tube I bought months ago, and a pair of old work boots. I’m doing my best. Don’t judge. I’m just the wing woman.

One week ago, Payton and I reviewed how we were going to apply his fundraising strategy to dating. His last goal? Get rejected 4 times in one month. His goal before that? Get rejected 7 times in one month. His current score: 0. Not because he’s gotten everything he wants. Mostly because he’s just avoided rejection.

Mostly, Payton doesn’t approach women he’s interested in or even could be interested in. He hangs out in a wide social circle. Wisely, he doesn’t spend his time hitting on women in that social circle. Word travels fast. So tonight I am going to be a wing woman and we are going to walk through the streets of San Francisco. Yes, this is the worst possible way to ever talk to anyone. Yes, this is the point. There should be rejection right and left. My logic is that anything after this will seem “easy.”

[Here is our intro to Payton.  Here is his run-down of women he’s interested in.]

Rejection #1: Triumphant Rejection at a hipster store

We pass by a store that literally is displaying three messenger bags in the middle of it. At the edges of the store are a few more things displayed, but not many. Gold leggings. A few pairs of jeans. Another few backpacks.

The store is also filled with people drinking beer.

We go in.

In the corner is a makeshift bar set up on plastic tables. Free beer. Perfect. That’s where most of the people are congregated. Surprise. There are plenty of women milling around with beers. I nudge Payton with my elbow. He doesn’t move. I sigh.

“Don’t over think it,” I urge him. “Just ask any question. Not a personal one.” He still doesn’t move. I do a demo the way I’d done earlier, with Edward (pt 1 with Edward, pt 2 with Edward).

Scanning the room, I see a tall white guy in the corner staring at his phone. I figure he’s an easy target, without friends to interfere or make him self-conscious.

“Excuse me, what is this event?” I ask him. It’s the most obvious question. It’s also a real one. The guy looks up at me and starts telling me about the launch of these fancy new bags. He points to the display in the middle of the store. I ask him some follow up questions. Payton is nodding over my shoulder. He’s gotten the point.

Unfortunately, the white dude now will not leave me alone. He’s describing the evolution of the store. Are all these people really into messenger bags? I cut him off and take Payton with me.

Payton instantly approaches a purple-haired Asian American girl in another corner, asking her the exact same question as me. It’s a good start. She also answers and he is able to strike up a conversation with her. It seems to be going well. I go get a free beer and chug it in the corner pretending not to eavesdrop. He’s asking about her skateboard, mentions he also lives in Oakland too.

“It’s easy to learn,” she says. “You should start.”

“I’d rather learn from you,” Payton says. I almost spit my beer out. It’s bold. Super bold. It’s also way, way personal for a less-than two minute exchange. In other words: perfect rejection set-up.

Instead of replying, the girl turns away from him. She spots me holding the beer vertically to my mouth.

“Hi,” she says. “My name is Nicole.” I swallow my mouthful of beer and shake her hand.  What a nice, awkward transition she’s made.  Really, I want to shake Payton’s hand.

On our way out the door, the white guy with the phone stops me again.

“Do you live around here?” he asks me.

“I’m visiting from out of town,” I lie. The guy looks disappointed. I grab Payton’s arm and walk out. Does this guy not see that I am with another man? Why is it when I’m with Asian men that white dudes will see me as “single”? Even when I hang out with any other guy friend and there is 20 feet of space between us, men will ask me:  Is that your boyfriend? Is that your husband? Unless he’s Asian.

“Me and that guy talked for long enough that it wouldn’t have been weird to get his number,” I explain to Payton as we go outside. I add:

“Good job on your rejection.”

Payton smiles proudly.

(continued in Blog #22)

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Each post is a great fucking adventure