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Matchmakers Tried To Set Us Up And, Um, It Didn’t Quite Work Out

It's tough out there.

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Brett: Hi there! I’m Brett, I’m 24, and I’ve never really been in a serious relationship. I’ve lived in New York for nearly two years now and have learned through plenty of trial and error that dating here can be exhausting. I’ve been on the casual dating app grind for the LONGEST time, and since that has been going sorta meh, I figured it was time to give something a little more unique a try.

Kristin: Hi! I'm Kristin. I'm 27 years old, and would mostly describe my dating life as one long, erratic roller coaster. I have quite a history of dating what my friends would call "jerks," like, secretly-has-a-girlfriend-that-I-discover-four-months-later type of a jerk. So I figured it was very much time to step outside of my comfort zone and try something new!

We volunteered to be set up by a boutique, high-end matchmaking service called Project Soulmate. The service is run by matchmakers Jenn and Lori (the latter previously had a Bravo show called Love Broker), and they typically work with 25 clients at a time who pay anywhere from about $25,000 to $60,000 for the entire process (they weren't kidding when they said "high-end"). For that price, they venture into the dating scene and advocate on your behalf, going to places like charity events and singles mixers, or, as we'd find out later, cold-messaging randos on Facebook. Their ~goal~ is that you're not single for longer than six months after starting their service — which is a hefty price tag and a big claim — so we decided to do a mini trial run and see what really goes down with a matchmaking service. Here's what happened.

Brett: I went into this matchmaking experience cautiously optimistic. Maybe this pair of love experts knew what was best for my single and helpless self. Since I'm so used to app dating, I was curious to see if a seemingly more ~legit~ dating service would actually get results. In New York City especially, if you make it past three dates without someone ghosting or something else going wrong, it’s a miracle, so the claim they can find a person’s soulmate seemed like a hard reach.

Kristin: While I would consider myself an insanely optimistic person in literally every other aspect of my life, dating is different. So as you can probably imagine, I was more than slightly skeptical at this entire experience, even after Brett tried enthusiastically convincing me otherwise. But this seemed like the perfect opportunity to try something new, and how bad could meeting someone for an hour for drinks be??

Brett: When I first met Jenn and Lori for my interview, they were super warm and welcoming, and they clearly had a knack for what they do. Before I knew it, I was revealing deep and personal details about myself, like the specifics of how I would want to raise my kids, my fear of divorce — you know, the fun stuff. It was like venting to a close friend over a bottle of Trader Joe’s wine. Then they asked me to hand over my Tinder profile so they could see who I was matching with and the conversations I was having with them, which turned me into a damn nervous mess and felt like more of a breach of privacy than handing over my social security number and Myspace profile. After getting a general idea of who I was, my general interests, and what I was looking for in a ~soulmate~, they were ready to set me up.

Kristin: Once we were on board, our matchmakers sent a questionnaire about our personalities and what we were looking for, and then we met up to chat about it all IRL. I was 1,000% more nervous about meeting them and discussing casual, chill things like "what I was looking for in my soulmate" than any date I've ever been on. But after chatting for half an hour, they felt like they had a good grasp on what I was looking for. Which is cool, because I still don't even have that figured out for myself.

A few days later we received our dating bios from the matchmakers to be sent to potential matches — mine said I was "dynamic" and that I'm a person who "loves to smile." It sounded a little bit more like a Stepford Wife than a real human, but for the nature of this experiment, I said great, and off our bios went into the matchmaking ether!

Brett: These would essentially be blind dates; all we'd see before them was the other person's bio. The bios were similar to those horoscopes where you think, Omg this is so ME… until you realize they could probably be applied to 99% of the people you’ve ever met. Like, who doesn't like to travel or love to smile? My first date was someone they first talked to by cold-messaging them on Facebook, which, huh, OK I guess. After my date was officially scheduled, the nerves set in. Oh my dear damn god, what had I gotten myself into?

For my first date, we agreed to meet up for drinks after work at this kinda bougie bar that was recommended by the matchmakers. It was definitely more ~upscale~ than I’m used to, since I am but a man of simple Two-Buck Chuck tastes, but I rolled with it (but really though, a glass of wine was $17, my god).

We got to the bar just before 8 p.m., and it seemed like it was off to a smooth start. We covered what we do for work, our love-hate relationship with New York depending on the season, and how we had gotten into this whole being set up by a matchmaker situation, with no real awkward conversations gaps. It seemed to be going pretty well!

Then, about 45 minutes into the date, she went to the bathroom. So obviously I proceeded to whip out my phone to text Kristin the scoop. I also figured, Well, this seems as good of a time as any to say a prayer for my wallet and order another glass of wine. She came back as the glass was being handed to me and said, “So, I’m usually home by nine...” It was 8:50. I nervously chuckled, took the hint, and started sipping my wine a little faster while I resumed our conversation. She then said, "No, seriously, like, chug it." I was taken aback, but I downed the wine a little bit faster. We again went back to our conversation. As I took a brief pause from my dazed wine chug, you know, to gasp for breath, she AGAIN said, "No, I’ll keep talking, you keep chugging." At this point I was completely flabbergasted, but I downed my painfully pricey merlot like I was getting iced, and paid. We must have been out of the bar not even five minutes after she came back from the bathroom, and she was immediately in a cab on her way home as I was on the curb left to process what the heck just happened.

Now, if I had said something offensive or off-putting, I can understand leaving like you’re Cinderella bailing from the ball at 11:59, but the conversation we’d left on was thinking of places to take her mom that weekend while she was in town visiting. I’ll admit I was a little shook up after this for a bit! It's totally understandable if you’re not feeling a vibe with someone, totally cool, but finding the need to escape with such a sense of urgency not even an hour into the date was a little disheartening. So needless to say, it was not a match.

Brett: Date #2

Since the first date wasn't quite a fairytale ending, the matchmakers set me up with another potential match that would hopefully allow me to drink at a non–frat boy pace. I was definitely going into this one less hopeful and way more low-key terrified, but I’d made it this far, so may as well finish this out. The second date was Katie (her name isn't actually Katie, you get it). She was passionate about her career in fashion, she was close with her family, and she was super bubbly. The matchmakers were SURE this one would be better than the first…and it was!

This date was at a more low-key bar, so I admittedly felt more at ease, and it ended at a pizza place, which is the way all dates should end, tbh. It went on two hours longer than the first date and was overall so much better. She was super conversational and seemed genuinely curious in getting to know me. She had a put-together and trendy look, she was clearly career-driven, fascinating to talk to, but all in all, there still wasn’t that natural chemistry there, and by that I mean I could tell early on she wasn't really into it ~in that way~, which naturally fizzled my own interest. It goes to show that someone can be theoretically great on paper for you and you can get along with them super well, yet it still doesn’t necessarily mean you’re going to click in a romantic way. Back to the drawing board for me!

Kristin's Date

Kristin: Between you and me, I had little-to-zero faith in this whole blind date situation. Having a connection with someone you meet out or on an app and already slightly know is rare enough as it is. I figured I would pretend I’m Andie from How to Lose a Guy in 10 Days and spend a few hours with this guy, probably never see him again, and then write about what matchmaking was like. But naturally the joke was on me, and I was proved very, very wrong.

After a few strike-outs with my first potential date options — one was a bit older than I was comfortable with, another "didn’t like girls that wore red lipstick” — I finally landed on a guy we’ll call Jake. He was 33 years old, career-driven, and liked “trying new restaurants and reading.” Great. I also love food and books. I said yes and we agreed to meet at hotel bar a few days later.

I met Jake at 7 p.m. on a Saturday night, and after probably 15 minutes, I realized we actually had that elusive immediate ~connection~ that seems borderline impossible to find in NYC. The conversation was effortless, we had a lot in common, and we both admitted how genuinely shocked we were at how good of a time we were having (can you tell I don't like dating??). Six hours, four glasses of wine, and a plate of pasta later, I hopped in a cab and headed home, feeling like I was possibly being Punk'd. Did they somehow actually have this whole dating thing figured out? Were they paying him?? I was determined to find out.

The next day I saw Jake again for another six-hour adventure. He taught me how to play golf at Chelsea Piers and we shared a bottle of wine over dinner — I felt like I was living my best rom-com life. Going into this with zero expectations of probably ever seeing this person again (being interested enough to go on a second date in NYC is a feat in and of itself), I couldn’t believe they so quickly and easily managed to match me with someone’s personality I meshed so well with. Here I was — me, who rolled my eyes at the thought of this experiment ever working — actually meeting someone that I wanted to keep dating. Maybe there really WAS some weird matchmaker intuition??

Jake and I continued to see each other over the next couple of months. I really liked him! Everything was going great, really great, until one day while he was traveling for work he fell off the face of the earth. As in, we were in the middle of a text conversation about how our weeks were going when mid-convo he just never replied. Ever.

Maybe his thumbs fell off? Maybe his plane diverted to the island on Lost? Maybe he fell in love with his intern? We'll never really know. But what I do know, is that no matter how you meet someone, it doesn't change the fact that sometimes people are jerks. The matchmakers couldn't believe it. I couldn't believe it! Feelings change, life happens — but in an ideal world, we’d all be mature adults and communicate our feelings instead of abruptly turning into Casper. But, alas, a great way to get over someone is to realize they are not who you thought they were!

Brett: Though I’m still soulmate-less AF, something I did take away from this was trusting my own ability to tell whether there was truly chemistry with someone, and feeling validated in my own ability to do that. When it comes down to true, in-person chemistry, that’s something you alone can decide. You can look at someone’s profile picture, see your mutual, fairly nondescriptive interests in your bios like "hanging out with friends" or "watching Netflix," and on paper it could totally match up, but the chemistry could still not quite be there. That’s super frustrating, but also perfectly understandable and OK!

As for the matchmaking service, sure, going through a matchmaker can take stress off of the emotionally taxing process of swiping hundreds of profiles or approaching someone at a bar, but is it worth the price tag of half my salary or more than 10,000 bottles of my lovely Two Buck Chuck wine? I'm gonna pass. I think I’ll be heading back to my roots with the vast sea of online dating apps for now. See you all on Tinder! 👋

Kristin: So, yes, this experiment started out great and then crashed and burned real hard — but I can't lie, it was amazing to have an email pop up with a new date scheduled, no effort on my part but to actually show up and see how we got along. In New York City it's exhausting enough to just, like, be alive, so it was much faster and easier than going out, or sitting at home and swiping right for 20 minutes. I got an email with this man's bio, said yes, showed up, and it worked. But at the end of the day, you can’t really "matchmake" chemistry. It's either there, or it isn’t. And even when you do have a connection, it doesn’t mean it’s going to work out, no matter how you met that person.

Whether you meet someone out, or hire an expert to set you up, there isn't one way of dating that holds the ~secret key~ to relationshipdom. If you have absolutely zero spare time — and are fortunate enough to afford it and/or win the lottery — maybe a matchmaker is for you. But no matter how you meet your date, the result is basically the same: Sometimes it works out, and sometimes it doesn't.

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