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Apr 27, 2020

I'm a Dating Coach. What's That Like?

How an Ex-Wife / Matchmaker Found Her Dream Job

Talking about my job in finance was a great conversation stopper. The only thing more effective was the phrase, “I left work to focus on my kids.” 

But now that I’m a Dating Coach I’m the belle of the ball. As soon as I utter the words...BAM! I get hit by 100 questions: 

“Wait, what?”

“What do you mean?”


“Is that a real job?”

“Omg, I have the worst dating stories. I should write a book.”

Well, since you’re all proverbially gathering around me right now, let me tell you the tale of the ex-wife/matchmaker who became a love doctor.

How an Ex-Wife Became a Matchmaker

Once upon a time, I was 34 and divorced with two little kids. I’d just moved to NYC, single for the first time in a while. In fact, after having met my ex husband at 23, I hadn’t ever really dated. And here I was, in the dating capital (hell) that is NYC.

The timing was perfect. Match.com was just getting started. I threw myself into this whole new world like a rabid animal. I fell in love with dating. It was the first time I’d been able to meet single people.  And if it wasn’t to find love, it was a welcome break from hanging out with toddlers.

Somewhere in the mix, I’d joined a matchmaking database. Two years later I got a call. The matchmaker found my profile for their client. Would I meet them for coffee?

There’s only one answer to that question. 

Long story short, instead of dating their client, I joined the company and became a matchmaker. What that’s like is for another time.

How a Matchmaker Became a Dating Coach

You know how you can be great at shopping but not so great at running a store? Yeah, a little bit of that. But what I lacked as a matchmaker I made up for in connecting with singles and learning their stories.

After meeting with hundreds of people, all searching for The One, it became clear to me that finding the right person wasn’t really the problem. It came down to all the stuff that happens after meeting somebody great. Does that make sense?

Ready for a little math? Consider the 43 year old single woman who has had one 3-year relationship. She has been dating since age 20. That’s 20 years of dating. Assuming she met five new men a year, that’s 100 men.

Now, out of all of these men that she chose to date, what are the chances that not one of them could have been The One? And if the problem wasn’t meeting the right guy, then what was? 

Why I Fell in Love with Date Coaching

Figuring it out, answering that question - that’s date coaching, that’s what I do. Here’s what I love about it.

I get to meet people who are ready for change. They’re curious, introspective and want to learn about themselves. They’ve accomplished a lot. They’re super smart. And most of all, they trust me with the most important thing in their lives. 

Through our work, I get to see real change! There’s nothing better than a true “Aha” moment, like when my 65 year old client went on an amazing date for the first time in a decade.

Or my 28 year old client, who, after getting ghosted by his date, went to the comedy show alone. During the intermission he messaged a girl on Hinge. His now girlfriend.

How awesome is that? And I got to be a part of it.

The Not So Great Stuff About Being a Dating Coach

But like any business it also has its challenges. In the beginning, finding clients was hard because date coaching carries a certain stigma. Finding love should just come naturally right? Only weirdos need help. Well, if you think that’s true have a look at the divorce stats and the 100+ million Tinder subscribers.

Then there’s all the business stuff, like creating an LLC, accounting and getting your name out there. I can’t tell you how many networking events I went to. Friends of friends, figuring out Google SEO and the rest. But like anything else, I figured it out.

Okay, What's it Really Like?

For all of its challenges, becoming a dating is one of the best decisions I’ve ever made. I get to work with the best people. My job is literally to talk about dating. Think about dating. Read about dating. Write about dating. And best of all: all of my bad dates are now career building (and arguably tax deductible?).  

The last reason I love my job is a selfish one. Seeing all of these clients go through my process has made me a better dater. I’ve learned to be more tolerant, empathetic and open. I put myself out there in ways I never would have, video dating being a prime example. 

My clients love working with me because they know I care. I don’t sit comfortably from the comfort of my relationship and tell them what to do. I walk the talk and I know how hard it can be. 

So there you have it. I love my job.  

What’s it like being a dating coach? 

It’s awesome.