【Female Instructor’s Strange Private Lesson (2025)】

After seven years,Female Instructor’s Strange Private Lesson (2025) I was done with dating apps.

OK, I wasn't. Who was I kidding? I'm not an extrovert, and I write about sex and dating for a living. My "done" with dating apps didn't look like deleting my accounts or chucking the apps in a figurative trash can. But I was done relying on dating apps alone. 

I didn't know at the time how true this would end up being, or that another social media platform would be the catalyst.

Online dating sans dating apps

It was 2021, COVID restrictions had begun to lift, and I was ready to meet a steady partner. I was 27 years old and had been on dating apps since my study abroad semester in London in 2014, when I only knew a handful of people in my program. Years later, living in New York City with a support system around me, I had no excuse. It was time to get creative and try something new.

At the beginning of the pandemic, I watched a lot of YouTube and discovered Kurtis Conner, a comedian who was going on tour in October. Knowing Conner's style of online engagement, this was a chance to get a date somewhere other than "the big three": Tinder, Hinge, and Bumble. Instead, I scooped two tickets to one of his Manhattan shows.

At the time, Conner frequently replied to and retweeted his fans on Twitter (it was still Twitter back then!). If I didn't find someone to ask out IRL, I'd tweet at the social media-savvy comedian to help me find a date to his sold-out show. 

As the introvert I am, I didn't find a date IRL. It was time for the next stage of the plan: tweeting.

"Is this even a good idea?" I asked my friends. I felt vulnerable tweeting that I was looking for a date, let alone having my plea retweeted by someone with millions of followers. But my friends assured me the plan was solid. With risk comes reward. 

A week before Conner's show, I tweeted:

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A few minutes later, a message popped up in my inbox: "Omg I'm so invested in this now (also I am free but I assume u have 7,000 applicants at this point)."

The message was from Kat Tenbarge, a fellow journalist and Twitter mutual. I didn't know Kat personally but I was impressed by her work. Between that and the fact that she's cute, I was floored that she DMed me.

"Haha well you are the first person to DM and I'd love to go with you!" I replied, two minutes later, according to screenshots. It was true. Other people did DM me later, but Kat was the first.

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We exchanged numbers and agreed to meet at City Winery, the show venue and a restaurant that specializes in wine and cheese.

My first date from Twitter

I, chronically early, arrived first to line up in front of the venue. I had never met Kat before, and I had the same first date jitters I always did. That was on top of the classic sapphic quandary before a first date: Is this even a date?

Kat had shared photos for Lesbian Visibility Day earlier that year, so I knew she liked women, and I was pretty vocal about my bisexuality (including writing about it for Mashable), but still. We didn't explicitly say it was a date, and while I hoped it was, I also left room for the possibility that she just wanted a new friend.

Kat, chronically late as I would later learn, arrived after me. I had noticed the line's demographic and texted her how many femmes were ahead of me before I scoped out seats by the stage for us. I ordered a cocktail to ease my nerves and a charcuterie board for us.

Once Kat arrived, we chatted for a few minutes before the show started. Our conversation flowed easily before it was cut off by Conner starting his set. Afterward, we headed to a different bar near our neighborhood in Brooklyn, finding out we lived only four subway stops away from each other. 

Before the end of the night, I was emboldened by the alcohol and asked if this was indeed a date. With a bright smile I've seen many times since, Kat confirmed that yes, it was a date. Emboldened even more, I asked if I could kiss her. Again, she said yes(!).

I left tipsy from cocktails and giddiness. Not only was it a great date, but I landed it through my creativity (and, fine, a little help from Twitter).

A few months after that, I asked Kat to be my girlfriend and was finally, actually done with dating apps. I deleted my accounts and the apps off my phone and never looked back — and now, we're engaged!

UPDATE: Feb. 28, 2025, 11:06 a.m. EST This article was updated to announce Anna and Kat's engagement.