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My therapist’s orders: Go on 35 first dates

L.A. Affairs
Just following doctor’s orders.
(Verónica Grech / For The Times)

“You don’t go on that many dates.”

The critique came from my therapist, at our first session of the new year, the new decade.

It was also the day after I turned 30.

She was right, even though I hated to admit it. For as little as I was engaging with the dating-app scene, it was still sucking the life out of me. I was coming off a six-month app hiatus, but I’ve been using them on and off for nearly six years.

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There was no anger. She understood what I was going through. She had been divorced for over a decade, and had been in a few relationships since. And I was just coming to realize that I wasn’t ready to be in a committed relationship just months after ending a 23-year marriage.

“There are 52 weeks in a year,” my therapist continued matter-of-factly, “I know you can’t go on a date every single week, but how many do you think you should be going on?”

This was a compromise; an acknowledgment that as a high school teacher I experience a unique exhaustion that meant there would be no room for late-night, midweek dates involving blowing out my hair, flirting and drinks for some of those weeks. But it was also a firm push that I needed to get on board with her statistics-based dating approach. If I upped my number of dates, I upped my number of chances of meeting the guy for me.

I mentally imagined a calendar: There are 20 weeks in this semester, I could go on more dates during the summer, then the new school year would start, another 20 weeks …

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After months of widowhood — after consoling family and friends had scattered back to their own lives — I decided to give “it” a try. What is “it”? Online dating.

“I think I can do 35 first dates,” I declared, regretting the decision as soon as the words came out of my mouth.

“Good, I think that’s a reasonable amount,” she replied, satisfied that I was being agreeable. “Thirty-five first dates in 2020, that sounds more like it.”

I suddenly felt as though I’d just lost a negotiation I hadn’t realized I was a part of.

I left her office, simultaneously freaking out while working on my new Hinge profile. Just think of this as another challenge. Don’t get emotionally invested. My inner monologue went against everything I thought dating should be about: mainly, taking it seriously, being emotionally available. While I am able to detach from my emotions in a work setting, it was new territory for me to think of my dating life and (what should be) romance in such clinical, numbers-based terms.

Within 24 hours I had 20 matches, 15 conversations started, and about five that actually seemed to be going somewhere.

Not bad, I thought. Shouldn’t be too hard to go on three dates a month.

Issues started when, having initiated swiping while visiting friends in West L.A., the app began matching me with West L.A. guys. Not that there is anything wrong with West L.A. guys, but I live firmly in Northeast L.A., which any Angeleno will tell you can be a distance as insurmountable as crossing the Sahara Desert on foot. Cory from Culver City was pretty enthusiastic about meeting until I let him know where I lived (which was not in fact 10 miles from his current location). Something “came up,” and he had to reschedule our date for “another time.”

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No worries, Cory. I wasn’t sure if I “willing-to-sit-in-rush-hour-traffic” liked you, either.

I instead scheduled a date with Jacob, who lived downtown. It was Sunday and we made plans to get drinks after work on a Thursday. I can do this, piece of cake! Two hours later, another match, Will, suggested we also meet up that week.

“I can do coffee on Wednesday?” I responded, and immediately regretted it.

I hate coffee dates. Alcohol is fundamentally necessary when meeting someone from the internet for the first time (a lesson I learned the hard way), but I knew I couldn’t do two nights of “drinks” dates back-to-back. The lack of sleep would show, and my nosy seniors would find a way to pry into my personal life (truly their favorite class activity).

With my Wednesday coffee date and Thursday happy hour set, I slid into my Sunday afternoon with overblown confidence that my years of dating app experience should have taught me to dismiss. Three dates a month, pshh, I got this. Around 2 p.m., Ed, another match, asked, “So what’re you doing tonight? You want to get a tea or something? Is 7 OK?”

Could I do this? Could I knock out all of my January dates in one week?

“Sure! There’s this cute tea spot on Sunset in Echo Park…”

New year, new me indeed.

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At 3 p.m. Ed confirmed. At 4 p.m., “I’m stuck at work, won’t be able to get out of here until 8. We can do tomorrow, or Tuesday.”

Stuck at work? On a Sunday? I spend every Sunday doing some amount of work at home, but never in a way that I’m actually stuck, which is a similar situation to nearly all of my friends of varying professions. I looked back at his profile to see what kind of work he does; no job listed. Not even something as vague as “owner” with no company or industry identified (which is something I have seen with annoying frequency on dating apps).

“OK, cool,” was all I said. Having already felt lukewarm about Ed to begin with, I wasn’t going to put in the effort to reschedule. If he wanted to meet up, he could message me. In the meantime, by the end of this week, at least according to my therapist, I’ll be two dates closer to finding the perfect guy for me. Unless he lives across town in Culver City. Then we’re doomed.

The author was born and raised in Los Angeles, and is a high school teacher.

Straight, gay, bisexual, transgender or nonbinary: L.A. Affairs chronicles the search for love in and around Los Angeles — and we want to hear your story. You must allow your name to be published, and the story you tell has to be true. We pay $300 for each essay we publish. Email us at LAAffairs@latimes.com. You can find submission guidelines here.


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