Dating with Anxiety
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I Hung Out With a Friend While He Tried to Work Up Courage to Tell a Girl She Was Pretty and MAN It Was Stressful

We hovered around him like buzzards surrounding a fresh carcass.

“Just get in and get out,” Friend 1 shouted at him.

“It’ll be over so fast!” Friend 2 added.

“Come on, don’t chicken out,” Friend 3 contributed.

“If you don’t do this then you’re dead to me!” Friend 4 screamed, spittle flying from their mouth and also I should mention Friend 4 was me.

We were out at a bar for our friend’s 24th birthday. The rest of the group, myself included, had a mean age that fell in the 30 – 35 age bracket. However, we’d all met and bonded at the same dark, cramped bar here in Seattle, all rooting for the same English soccer team. They are friendships formed over shared hatreds of opposing teams and shared beers at 6am kickoffs.

Our spring chicken of a friend, the one now turning 24, will sometimes talk about crushes with us at the bar, girls he might find cute or intriguing. We tend to grill him, digging furiously through his hesitant collection of information, foraging for clues of scandal or intrigue. Ever the gentleman, he rarely gives us much to gnaw on.

But then we went out for his birthday. At a bar we don’t usually frequent, one located directly across from a University downtown, and one that transforms into a college party at the stroke of 10pm like some perfectly contoured and styled Cinderella-building. We got there at 9 and within an hour I became acutely aware of how long it’s been since I hung out in a college bar. I was like some white lady Hannibal sitting there staring at the 20-something girls saying “look at her skin” under my breath.

Our birthday friend mentioned he thought a girl was pretty. He said he wished he could tell her. We pounced on him like he’d casually mentioned he had a million dollars stored in his coat pocket.

“Just do it casually,” Friend 1 said.

“Don’t overthink it,” Friend 2 said.

“Be yourself,” Friend 3 said.

“Do you think she uses a special moisturizer?” Friend 4 said.

We threw endless suggestions at him, tossing baseballs of empty cliches at his face as if it would help.

His face quickly dissolved into a weird combination of anxiety and determination and suddenly I FELT ANXIOUS FOR HIM. Stupid empathy.

For what seemed like hours (but was probably more like 20mins) we watched him stand up, take a few steps in her direction, then come back to our table. He’d stand, shuffle a bit, mumble a few words, then sit back down. Over and over again. It became painful.

“She’s on her phone,” he said.

“There’s a guy at her table, I can’t tell her she’s pretty while a guy is there.”

“Her beer is almost empty, she might be getting up soon.”

“She’s back on her phone.”

After his sixth or seventh attempt where he discovered another reason not to talk to her I grabbed my wallet and pulled out a dollar. Anyone who knows me or reads this blog knows I LOVE a good bribe and by bribe I just mean a small symbolic object you get if you take a new step or do something scary.

I told him he would get the dollar if he went through with it.

After the eighth and ninth attempts he stood at the table staring at the dollar bill. At one point he muttered, “I want that dollar.”

Finally, he stood and began walking towards her. One of our friends stood and walked a few paces behind him, sheep-dogging him if you will, not allowing him to turn around this time.

And, spoiler alert, he told her she was pretty. She said thank you. And he got the dollar.

Guys, this was stressful. For any of you reading who are out on the dating scene trying to work up the nerve to talk to someone you think is attractive I BOW DOWN TO YOU. The fear of rejection is real and true. The depth of vulnerability that’s required to even do something as “simple” as telling a woman she is pretty, is monumental. So go ahead, give yourself a damn dollar the next time you do something bold.

Our 24-year-old friend doesn’t talk about his crushes all that often. But now, if he does, I’m going to flap my buzzard wings, fly away and leave him alone. I’ll simply tell him, “you do you, boo boo.”





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