I Went To A Dating Coach For Love Advice & Didn’t Anticipate What Came Next

I was having a bad day. I hadn’t stopped working since 7:30 in the morning. It was 8:15 in the evening when I went to a dating coach. I was mega-caffeinated yet totally exhausted, fresh from what was supposed to be a 40-minute train ride that instead took an hour and a half. I was too warm, hangry AF, and I was terrified about what the coach, George Kong, would say.

Just like Hitch, George cures your dating ills, fixing the problem from the inside out, to date smarter not harder, in an objective and nonjudgmental way. He’s spent his career as a connector in various industries, including as a matchmaker at a dating concierge; now, he brings his dating expertise to the masses via byGeorge, his own date consulting company. He’ll audit your dating app profile and suggest changes, offer live help when you’re on a date (called Date Night SOS) if you need support during your date, refresh your dating life with a series of consultations, or a combination of the three. He knows what he’s talking about, and tonight he’s talking to me about my own dating life.

To be fair, there’s some George already knows about me, and not just because I filled out his standard byGeorge questionnaire that shares a bit about your background and what you’re hoping to learn. We have been friends for nearly seven years, and also dated briefly all those years ago. But tonight, in his striped button-down shirt and vest, hair swept to the side and glasses perched on his face, George is as professional, objective, and nonjudgmental as he is with all of his other clients. Even when I am literally weeping next to him at a rather hip hotel bar twinkling with purple neon lights as The Rolling Stones’ “Brown Sugar” and George Michael’s “Freedom! ‘90” play overhead.

Elyssa and George at her birthday party in 2018.

I am weeping because soon after I sit down, I start telling George about James*, who I met six months ago in South Florida, where I’m from and where he lives. After speaking regularly all that time via text then Skype, slowly but surely making emotional declarations to each other and spending time together when I was home, I had the extreme misfortune of falling in love with him: this man who lives over 1,200 miles away from me, and would possibly live even further away soon. Working on short contracts in tech, there was a possibility his next move would take him as close as Chicago or as far away as London, Berlin, or Munich. He’d know within the month. He wanted us to remain honest with each other about how we were feeling, and to that point, I’d done my best. Mostly.

I had known for a while that I loved him. It was one of those things I heard my brain say when he talked about books he loved or when his rapid-fire wit reduced me to a heaving pile of laughter, and then it just never left. But I never said how I felt. I didn’t think it was my place to further confuse or burden him while his life was a self-described mess and he was figuring out his next move.

In the meantime, to stay sane, or so I thought, I sent myself on a slew of dates. I had been on perhaps as many in a span of two weeks as I had been in the entirety of my nine years in New York. I was single, after all, I better act like it! I couldn’t just wait around, I needed to live my life! Or whatever other nonsense I was thinking at the time. So I went to wine bars and dive bars and sushi bars and cocktail bars and said my life story over and over in however many different ways you do that to people you don’t know in rapid succession. But when the dates were anything but good, they were the worst. Mediocre and terrible dates left me in a puddle of tears: none of them were James. Why was I doing this? I felt like a rabid raccoon foraging in the garbage.

I didn’t want to go on a date with some rando from Hinge. I wanted to be with James, and for a multitude of logistical reasons I couldn’t be. So I had to turn to George for advice.

George listened studiously, remaining quiet and taking notes until I finally exhaled and took a sip of my wine. He offered me a handkerchief, one of the ones he always keeps in his pocket. And then he said the thing I was hoping he wouldn’t say. “What’s the worst that happens if you put it all out there? What if putting it out there makes it easier?” he says. “Maybe he’s looking for a reason to be somewhere.”

But what if he isn’t? What if I say this thing and he disappears? What if I burden him and confuse him even more than he already is? Doesn’t this not make any sense? What if we haven’t spent enough time together? What if we haven’t known each other long enough? What if, what if, what if… I hear myself making excuses. I hear myself being a coward. Plus, George is concerned about the number of dates I’ve been going on, as if I’m trying to self-medicate. He’s right. I delete the dating app I was using in front of him and I don’t upload it again.

“This digital age we live in makes it easier to connect, but it is more confusing because we’re not fully there," George says. "We, you and I, we’re of the age where we still have these beliefs about what connection’s supposed to be, but you’re already acting outside of it and your emotions are being built digitally. You’re building this. It’s happening. If you were to share anything, everything, and he disappears, then that’s what was gonna happen.”

In other words, James would never have been mine to begin with. And wasn’t it better to know that now than later? And in a more positive light, wouldn’t it be better to give James all of the information he could possibly have when it comes time to actually make a decision? Wouldn’t it be better to just be honest, as James himself had asked me to be?

“I think you’re safe to tell him,” George says. “You know the answers, Elyssa. I’m sorry for doing what you expected me to do.”

"Ughhhhhhhhh," I groan. We laugh. I take another sip of wine.

“Shall we call it a session?” he asks.

“Yes,” I say. “I think I’ve used my time.”

I wipe away tears, hoping there are no mascara streaks on my face. We walk out into a crisp yet wet New York night, lights of the Garment District bright over head, cars honking and flying past in the street. I know what I have to do.

*Name has been changed.

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