“Your grammar is kind of turning me on, I won’t lie,” I said to Claire, a girl I’d met on the dating app Bumble. “And sorry about the comma splice.”

“I do take pride in my grammar!” Claire responded.

We’d been going back and forth for a few days on the app. After conservations about my book, her “empire-building” business selling athletic wear, and our favorite weekend activities, I asked Claire on a date. I knew she enjoyed beach bars and lived about a half hour away from me, in St. Augustine, FL, the nation’s oldest city. “Pick your favorite beach bar,” I told her. “And the drinks are on me.”

“Sounds good!” Claire said, and we agreed to meet at the Salty Dog in St. Augustine that Friday night.

I texted her upon my arrival. She’d already eaten dinner at the bar/restaurant with her parents. I met her mom briefly, who was a tiny and well-dressed lady in her 80s.

“Your mom is very cute,” I said to Claire, once we took our seats.

Claire laughed and agreed.

She was in her early 40s and actually looked better in person than she did in her profile pictures, which impressed me because many singles on the dating apps transform like a werewolf under the light of the full moon when you see them in real life—and that’s one reason I felt comfortable having the lady from Bangladesh touch up my profile pictures.

Even though I’m usually pretty oblivious when it comes to fashion (I once wore a ten-dollar T-shirt to a funeral), I couldn’t help but notice Claire’s ensemble, which featured designer jeans and a modest white top. With a slim and toned body, her sun-kissed neck and wrists were decorated with a dazzling array of pricey jewels,

It was a cool evening by Florida standards, with a temperature around 60 degrees.

There were only two seats available at the outdoor portion of the bar, one of which was positioned in front of a massive and grotesque cement pillar.

I sat in front of the pillar, with no view of the bar or ocean or anything, really. Just the pillar. I kind of felt like I was in prison, a place I’ve never been (such an accomplishment…).

When the bartender finally noticed me, I ordered a pale ale of some kind. I had to shout my order to her because she was practically deaf. Claire ordered a second glass of wine sometime later.

Inside, at the bar’s main stage, a scruffy gentleman in ratty clothing with a tobacco-tinged voice played a solo show with his weathered acoustic guitar in the background.

Claire and I talked about work, life, recreation, and then talked about work some more.

It wasn’t exactly a riveting conversation, but it was enjoyable at times and not awkward.

We had several laughs about my seat, with its view of the massive pillar, and then we discussed music for a while.

“I’ve actually been talking with some people about starting a band,” I told her. I’d placed a Craigslist ad a few weeks earlier seeking bandmates.

“That’s interesting,” Claire said. “What type of music would you play?”

“I tend to prefer rock music, but I’ve also written country and pop and folk songs. Probably a mix of everything.”

“I love country music. I used to hate it, but now it’s all I listen to.”

“I like some country—mostly the older stuff. Are you from around here?”

“No, I’m from New York?”

“The city or elsewhere?”

“Long Island.”

“Long Island as in the Hamptons, out of curiosity?

Claire nodded. There are few more privileged places in the world than the Hamptons, home to celebrities like Jay Z and Beyonce, Jerry Seinfeld, Alec Baldwin, Gwyneth Paltrow, and many others.

At one point during our first round, I recall seeing Claire gaze disapprovingly at my black tennis shoes, which was understandable in a way (I hadn’t upgraded my wardrobe yet and wasn’t sufficiently dressed for the occasion).

A couple then sat down beside us at the bar. Claire spent the next three to four minutes chatting with the woman about jewelry and fashion. Meanwhile, I sipped on my pale ale and stared at the massive pillar in front of me…

When Claire shifted back toward me, she promptly asked, “Do you want to get out of here? I’m thinking we should go downtown. There will be more stuff happening there.”

“Sure, that sounds good to me,” I said, lying. I was expecting our date would be a basic meet and greet, but if Claire wanted to spend more time with me, I was happy to oblige her, even though I knew that we probably wouldn’t spend more than one evening together.

It would be an experiment in exposure therapy for me.

Claire not surprisingly engaged with more people as we exited the bar, spending at least five minutes with some random old dude whom she claimed was a friend.

I sat in the waiting area, which was crowded by now, and pretended to use my phone for important tasks.

Her parents—retirees, obviously—had given her a lift to the restaurant, so I’d be escorting Claire into town.

In the car I had something I wanted to show her.

“You said you were into country music. Do you wanna hear a country song I wrote?”

“What? Why aren’t we driving?” Claire asked, buckling her seatbelt.

“I just thought you might like to hear a song. My phone is old and quiet, so you won’t be able to hear it well if we’re driving or at a noisy bar.”

“Maybe later. I wanna see if make it in town in time to hear music.”

“Okay,” I said, putting my phone away while thinking, I just offered to play music for you…original music.

It was a bustling Friday night in downtown St. Augustine, the city of lights. After offering me parallel parking advice, Claire had several more of what one of my personal heroes, Larry David, would call “stop and chats.” A stop and chat is a small-talk session with an acquaintance or stranger.

Larry despises “stop and chats.” So do I.

“You’re maybe the most extroverted person I’ve ever met,” I said to Claire.

“I am really extroverted,” she agreed. “I can’t help it.”

At that moment I knew, for certain, that we were not compatible. As an extreme introvert and a “highly sensitive person,” social interactions drain me like nothing else, and there was no way I could match Claire’s energy level or tolerate her constant need to be surrounded by strangers for more than a few hours at a time.

But I had time to waste on this night, and I knew the end result of my exposure therapy experiment with Claire would be useful to me in the future, both for reference and for my own personal development.

Over the next few hours, we barhopped, engaged in more “stop and chats,” listened to mediocre cover bands, talked a little with each other, talked a lot with people in our surrounding areas, participated in a singalong, and became progressively less interested in each other.

On our way to bar number three, Claire contemplated buying a hat for the evening (one evening, specifically) because she was cold.

We entered a gift shop.

“I’ll literally only wear this once,” Claire said, as she tried on a purple beanie with a button on top. “Should I buy it”?

“That’s up to you,” I responded.

And I actually enjoyed stopping at that little gift stop with Claire—my favorite stop of the night by far. I presented several of the most tacky items I could find to her, including a pair of sunglasses with neon green rims and an oversized, brightly patterned scarf that looked like it was made from the leftovers of a 70s couch, and suggested she purchase them.

And I made her laugh once or twice.

Basically everything I did with Claire on this date—the conversations with strangers, the singing in public, the bar hopping, and all the rest—was outside of my two-inch-wide comfort zone. And that’s why this evening of exposure therapy was beneficial to me.

The more often we step outside of our comfort zones, the more we can transcend our self-imposed limitations and discover new strengths within ourselves.

The next day, I texted Claire and told her I enjoyed the quiet moments of our date—the gift shop, in particular—and sent her a link to my song. She never listened to it, ha (I can track view counts via YouTube). But she thanked me and said she had a good time. There would be no second date.

Despite being a country music fan, Claire didn’t want to hear my song, “Cuttin’ the Backwoods Down.” But it’s featured below if you feel like checking it out.