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How to Flirt with Boys When You Have Crippling Social Anxiety: A Memoir

Viewers across the nation cringed as Jeb Bush remarked that he was looking forward to seeing the new TV drama Supergirl because the lead actress “looked pretty hot.” My roommate and I must have watched the clip ten times, dying laughing and wondering how someone could be that pathetically awkward, especially on public broadcasting. Deep down, I secretly sympathized with the guy because I felt like I could relate to him on a personal level. And that’s when I realized… I am Jeb Bush ‒ that is, if he were an angsty 19 year old female.

giphyIf I had a dollar for every time an attractive male has informed me how painfully awkward I am, I would be able to upgrade to Spotify premium. I am what you would call an extroverted introvert, which is honestly the worst of both worlds in my humble opinion. I’m outgoing at times, but selectively social ‒ especially when it comes to meeting new people. In fact, my social ineptitude is truly my Achilles’ heel when it comes to interacting with members of the opposite sex.

There was the time I met my crush from the BC 2018 Facebook group in person the summer before freshman year, after texting back and forth with him for months. “You are making this so awkward,” he informed me as we sat in silence at Captain Frosty’s. Apparently he thought this insightful contribution would diffuse the situation, but it only made me clam up even more. I chewed on a french fry and nervously chuckled. “Yeah, I’m pretty sure I’m on the spectrum,” I blurted out. I immediately regretted the comment the second it escaped my lips, and cursed myself for not pregaming this excruciating encounter. Let’s just say, there was no second date.

unnamedAnother Jeb-like interaction that will haunt me for the rest of my life is the infamous “Guam” episode at Starbucks last summer. I made the mistake of asking my twelve year old sister to fetch our drinks because I was too lazy to make the trek to the front of the café. The second my sister disappeared, a twenty-something year old man in a military uniform slid into the seat next to me and struck up a conversation. I was not particularly interested making small talk, but I was flustered nonetheless. My sister approached right as he divulged that he was originally from Guam, to which I flirtatiously replied, “That’s a U.S. territory.” Smooth, right? I can only assume that he was overwhelmed by my impressive geography skills, judging by the lingering silence that ensued. You know you’ve got game when your entire family breaks into hysterics as your twelve year old sister reenacts the “painful” experience at the dinner table.

Intuitively, you might think that dating someone just as socially awkward as I am would serve as kind of a double-negative ‒ that our mutual awkwardness would cancel each others’ out; however, this theory was disproved when I went on a date with Tom* (*name has been changed to protect identity of the individual involved). I met Tom in a group setting and we really seemed to hit it off ‒ so much so that he ended up asking me out. We planned on grabbing dinner and a movie, in that order. Within fifteen minutes of one-on-one conversation, I realized that this date was a disaster. He charmed me with icebreakers, such as “Have you ever traveled out of the country?” and “If you could meet anyone in history, who would it be?” During dinner, he inquired whether or not I had ever been “bullied” in high school, before breaking into a sexy anecdote about how his classmates used to throw things at him in the cafeteria… That story was a real panty-dropper. The worst part was, I had to endure another hour of excruciating small talk with him before the movie started. Unfortunately, I had to break things off.

“It’s not me, it’s you. It’s usually me… but this time it’s actually you.”


My social anxiety combined with my impulsivity and lack of a filter when it comes to blurting out embarrassing comments often hinders my chance of leaving good first impressions on potential suitors. In fact, I’m pretty sure that if I lived back in the Stone Age, natural selection would wipe out my lineage pretty quickly. However, I’ve learned that my saving grace is that I am always able to look back and laugh at my humiliating social blunders. If you can’t laugh at yourself, who can you laugh at?

In the words of Jeb Bush, “Please clap.”

Photo 1, Photo 2, Photo 3

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