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I Deleted Tinder And Went To A Real-Life Matchmaker


matchmaker stock photo of dating

I’ve been breadcrumbed, ghosted, zombied and every other newly-coined word, which basically just means you suck at dating.


So, when the opportunity arose to become a “Basic Bachelorette,” for Matchmakers in the City, well, yeah, I took it. Look, I know there’s a stigma on matchmaking. But nowadays there’s a stigma on pretty much any way to meet someone, isn’t there?


“We can say we met at X,” is so commonly found on guys’ dating profile bios, it’s trope-y at this point. And who even meets anyone organically anymore? It’s so rare, it’d be weird in and of itself.


So why not trust a matchmaker? Alessandra Conti – co-founder of Matchmakers in the City, and my new girl crush – has six years experience matchmaking, plus a certification and celebrity clients. I, on the other hand, most recently got dumped by a guy with whom my only interactions for weeks had been relegated to texting and social media.


And that’s how I found myself in the waiting area of a luxe, Beverly Hills business complex, burning my tongue on steaming, complimentary Earl Grey as I waited for my first interview. Aly’s greeting couldn’t have been warmer, and when she strutted out to me in a slinky, black jumpsuit spewing compliments and hugs, left and right, I began to feel like one of the fancy, important clients from guilty pleasure shows I can’t help but binge, like Millionaire Matchmaker and Tough Love.


matchmaker beverly hills office

We exchange pleasantries as we head back to Aly’s office, an impeccably decorated, impossibly girly space like a women’s magazine in a movie or something I would’ve circled in metallic silver Sharpie in one of my old PB Teen catalogues. I love it.


After a bit of chatter about my most recent dating fails, Aly began the interview. My anxiety – which dictates at least a *bit* of perpetual nerves – aside, I was weirdly nervous to answer her questions, like it was an interview, and there were somehow wrong answers.


I mean, there have to be, right? Otherwise, wouldn’t I have just figured things out myself? At this point, I’m really feeling like one of those MTV dating show contestants, with all the cluelessness of confidently making the same mistakes that led you there, without the potential big cash prize.


Luckily, Aly is the bubbliest, most reassuring person (I’m not kidding, y’all. I want her to be my new best friend.) so it didn’t feel as awkward as I was thinking it would be.


matchmaker aly and writer
Matchmaker Alessandra Conti

Listing my celebrity crushes elicited an, “Of course you’d like Diego Luna,” and it suddenly felt more like girl talk with a close friend.


She asked if I’d be okay working with another matchmaker’s clients, if I’d be willing to date someone out of state, and if I were open to a man with children. We also talked likes and dislikes — What physical attributes did I look for in a man? What personality traits were most important to me?


How would my friends describe me? (Uh, hopefully nicely!) What would I want a guy to know about me? What did I want men to know about women?


Aly also explained the process. After completing my profile and reviewing my social media, background check, etc., she does the same for men in my area who meet my criteria. Once the matchmakers find someone who they think could be my “match,” then it’s time to go on a date… and they plan everything.


They choose a location, cross reference schedules so my potential match and I don’t have to go back and forth, and simply tell us where to be. Then we meet at the restaurant, and the rest is up to us. That part is especially alluring, since guys don’t seem to want to plan dates anymore.


Most men’s idea of a “date” is meeting at a bar and plying you with drinks — that sometimes they don’t even offer to pay for — in the hopes that you’ll get drunk enough to not care that insincere, practically scripted small talk about how awful Trump is or how much we hate LA traffic isn’t really enough groundwork to lead to physicality. (Not that I’m condemning a good make out, peace out (MOPO) — do you, babe — it just doesn’t feel the most conducive to finding a lasting, fulfilling relationship.)


matchmakers in the city group photo

Memberships with Matchmakers in the City are six months to a year in length, but the website claims that it usually does not even take that long to find a “love match.” Fingers crossed.


Of course, I don’t know if anything will come of this, since I’m not a priority member, so I don’t have, well, priority. I know you’re supposed to invest in your future. But I figure if I’m ignoring Sallie Mae’s calls, I probably shouldn’t spend too much on dating – especially in a city Aly dubbed, “the Baghdad of dating.” It’s just a crapshoot, right?


But all in all, it was a good experience. Now every time a skeezy guy tells me he’s “not looking for anything serious,” or calls me babe, because he probably forgot my name, I can be like, screw it. Who cares? I’m *in the system.* Plus, I got to feel like one of those fancy millionaires who have Patti Stanger boss them around on TV.


This was originally published on Entity Mag.

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A little about the writer

Kayla is an entertainment writer and reporter, editor at Ranker.com, and co-host of true crime and cannabis podcast, High Crime. 

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