Jarry: If you had told me that at some point in my life I'd be matched by a professional matchmaker, I would have laughed in your face, but here we are. In August, after I wrote about a party thrown by "elite" dating app The League, a "white-glove, personalized matchmaking company" named Three Day Rule contacted me on Twitter, saying that they'd love to match me. Naturally I was curious, because it takes either masochism or extreme confidence to ask someone who just eviscerated another dating service to review yours.
According to their website, TDR offers three-month and six-month matchmaking packages, costing $5,000 and $7,500 respectively. The six-month is the most popular, and it comes with at least six vetted matches, post-date feedback sessions, date coaching, and more, while the three-month guarantees only three matches and includes fewer features. (Alternatively, you can add your information to TDR's dating pool database for free and they will contact you if you seem like a good potential match for one of their paid clients.)
TDR agreed to set me up with one hand-picked match for free, so I arranged to meet in person with Erika, one of their matchmakers.
Side note: There is a certain amount of irony to a company that calls itself "a modern take on matchmaking" being named Three Day Rule.
Julia: As the love and relationships editor, my original role was to accompany Jarry on her first visit with Erika, mostly because all my knowledge of matchmaking comes from The Millionaire Matchmaker reruns and that one Fiddler on the Roof song, and I was curious to learn what the process was really like.
Coincidentally, the day before our appointment, I had just gone through a small breakup, and, due to watching the movie Serendipity too many times (twice), I crankily took this as a sign. "If you want, you can match me up as well," I said, already plotting both the future romance and the screenplay adaptation of my life (I really want Alison Brie to play me, if any casting directors are reading this).
Jarry and Julia.
Jarry: Julia and I each spent about half an hour with Erika answering questions about our dating preferences and backgrounds. My last relationship had ended earlier this year and I was looking (though not actively) for someone who could challenge me — ideally someone intelligent, driven, kind, funny, and all those other positive adjectives that sound great but are ultimately difficult to quantify in any meaningful way.
It was easier to specify what I didn't want: someone who was overly pessimistic or cynical, didn't have a sense of humor, took themselves too seriously, or used "bro" and "chill" often and unironically in conversation. I also wanted someone who wasn't a total garbage human being when it came to texting, which in New York City meant that TDR had their work cut out for them.
After the interviews, Erika explained how they find matches for their clients: Matchmakers look at TDR's dating pool database first and also seek out anyone in their extended personal and professional networks who might be a good match, sometimes even going out to appropriate places or events to look for a client's type. They vet all potential matches in person, trying to make sure there are no deal breakers while also testing for compatibility.
We repeated the interviews with a second matchmaker named Robyn a few weeks later to help them narrow down our prospects, who soon arrived in our inboxes.
Julia: I described all the qualities I'd need a guy I date to have: liberal (and cares about intersectionality), well-read to decently read (or at least won't say "I don't like books all that much," because that has happened to me, at least twice), artistic (but not pretentious/is willing to watch Step Brothers for the 100th time with me), and texts vaguely interesting things on time, arguably the most important trait of all. A while ago, I had a lengthy conversation with a friend about our collective attraction to a young Joe Biden, and I still stand by the theory that he would be the perfect man, if you added musical abilities and Louis CK's sense of humor.
"Yeah, I'd maybe try to not pair Julia off with anyone too hipster," Jarry chimed in. I nodded, secretly mourning the loss of potential flannel/tattoo sleeve combos.
After the meeting, Erika asked us to send a few photos of our exes so she could better understand our "type." I didn't think physical attributes said all that much, so I focused more on writing about each vaguely important relationship — why I liked that specific guy, why I think it didn't work out. It's easy to clump them all up as weird, artsy softboys, but it's also not 100% fair, because they have lives and personalities outside of their relationships with me. Seeing your exes as individuals is liberating! I recommend it.
They also sent us both really pretty flowers!
Jarry and Julia.
Note: Names of the matches have been changed.
Julia: After our second interview with Robyn, I got an email from Erika a few days later with information about Aaron. His photos didn't really say much about him, other than that he looked like a normal, objectively attractive person, which, if you've ever used Tinder, can be a low but important bar to reach.
He was said to be "looking for a woman who is independent, smart, and unapologetically liberal. He would love to meet a girl who is creative and has true opinions of her own." I was skeptical, because lots of men say that they want "real" women without realizing that "no makeup" often still means, like, a pinch of blush and concealer, and "true opinions" include ones that might combat their own. But I wanted to go in with an open mind, because if there's anything I've learned from dating so far, it's that people can surprise you.
I met Aaron at a wine bar in the West Village and immediately noticed that he, like the trendy establishment we were in, was polished in every sense of the word. He wore a loose chambray shirt and Adidas sneakers that remained a shockingly pristine white for someone who lives in New York. Even, dark stubble lined his jaw, lifted by cheekbones that definitely won the genetic lottery. A silver watch slid down his wrist as he lifted the wine menu.
Next to him, with the most sophisticated part of my outfit being a tiny gold pizza necklace, I felt a little like Allison in The Breakfast Club sitting next to Emilio Estevez, before she got her makeover. As he ordered his wine without stumbling over the foreign pronunciation, I couldn't help but remember how, earlier that same day, I ate a cupcake that temporarily stained my teeth green (and didn't realize until Jarry started cackling).
We talked about how we got matched (his sister knew someone in the company), then briefly zigzagged from topic to topic — why dating is so hard, our jobs, college (we went to the same university, but five years apart), how pretty L.A. is, TV shows. Bob's Burgers came up and I mentioned how I really relate to Tina Belcher.
"The one with the man voice?"
"Yes — well, technically Linda is also voiced by a man, but yes. Dan Mintz, he's great."
"Well, I just — I think she's written as this character who's nerdy and awkward at times but, like, isn't necessarily afraid to pursue the things or people she wants. I feel like teenage girl characters often only get to be one of those things."
He blinked and smiled, then turned to sip his wine.
We moved on, but even noninvasive questions like "so, what do you do at work?" felt skirted around, and in general, he seemed nervous about accidentally saying the wrong thing, lest it end up in the article. And he didn't — but the result was just two people at a table, limited to what could at the very most be a neutral conversation, because, at the core of it all, there was no physical attraction or chemistry on either end. It felt like what I imagined a date arranged by two overeager parents would be like, something we did out of some mysterious obligation, to say we tried.
The date lasted two hours, and two glasses of wine each. He insisted on paying, we left with an awkward, rushed hug, and, the moment I saw him disappear into a cab, I did what I wanted to do the entire time — eat a questionable slice of pizza and go home (BBQ chicken, 7/10, would eat again).
Jarry: I ended up getting two matches because the first match, Matt, turned out to be someone I already knew — I had matched with him a year earlier on Coffee Meets Bagel, but started dating someone else, so we never met. The second match was named Willy, which made me immediately picture a small child. (He was actually 26.)
Three Day Rule felt that Matt was a "spot-on match" for me — he worked in tech and was smart, well-educated, driven, had "intellectual humor," and was passionate about photography. He seemed put together but also fun, and I knew we had things in common from chatting before, so I was excited for the date. (The only downside was hearing enough jokes about fate from Julia to last me several lifetimes.)
On the other hand, TDR thought Willy, who worked in film, was "creative," "kind," "confident," "intelligent," "quick-witted," "creative" (again), "kind" (again), "caring," "sincere," and "driven"...which was an absurd, slightly suspicious amount of positive adjectives to fit in two short paragraphs. I had to double check that "Willy" was not actually a Craigslist listing for a Manhattan apartment.
Unfortunately, Willy's humor was described as "sarcastic and dry" (the opposite of my type), and I wasn't attracted to him at all. With his shirt unbuttoned perhaps one button lower than necessary in his unsmiling photos, Willy came off as a brooding Hip Film Guy. But TDR was "super confident" that we'd have a great date and a lot in common and said he was "so excited to meet."
That statement could not have been further from the truth, because Willy spent the better part of the date complaining about how he felt he'd been forced into it and how annoyingly persistent the matchmakers had been. (Both he and Matt knew I was writing about the dates and could've said no at any time.) "The whole thing is a bit weird in general if you ask me," Willy said, even though I did not ask him. I was on a date with a grown man named Willy for a BuzzFeed post, so I have to wonder who really got the shorter end of the stick. (Again, names have been changed, but it was very similar.)
We met in a restaurant on the Lower East Side that he goes to every night anyway, which is funny for someone repeatedly described as really, really creative. (TDR had also said that Willy's humor "was always on," which is the only thing I laughed about the entire night.) It actually seemed like they had barely vetted him, perhaps because he was a friend of a friend of one of the matchmakers. Willy was extremely negative (something I'd said would be a deal breaker), especially about dating apps, which he thought were weird and "would definitely never use" because he was better than that.
"I'm reading Dubliners right now. James Joyce is my favorite author," he said, and then proceeded to list a few of his other favorite writers, all of whom were dead, white, and male. When I read him the line from his bio that said "He needs a woman who can appreciate that his humor is always on," he snapped back, "I don't need a woman." We spent the rest of the date in uncomfortable silence, probably made more uncomfortable by the fact that I was eating a rather phallic Austrian sausage. When the bill came, he didn't offer to pay, and because he'd ordered drinks before I'd gotten there, I ended up paying over $15 extra.
The absolute kicker was when I found out his last name was Willerson (again, not his real last name but you get the idea) and that his given first name was actually a very common male name but he chose to go by Willy instead. I would just like to reiterate that out of the 8 million people in New York City, I was matched with a grown man who goes by the name Willy Willerson BY CHOICE.
My friends also have strong feelings about this.
I had a date with Matt the next day, and he would have had to run me over with a U-Haul truck to make a bad impression after my date with Willy. We met in Brooklyn Heights to walk along the pier and watch the sunset before heading to a quaint little Italian restaurant nearby. He was easy to talk to — we somehow talked about everything from conceptual art to functional programming languages over tagliatelle — and he seemed like a really great person overall, smart and funny and pretty much everything else TDR had promised. I was impressed and had a great time, enough so that there's not much else to say. After all, happy dates are all alike; every unhappy date is unhappy in its own way.
Exactly three days after the date (the irony is not lost on me, Three Day Rule), he texted me and we planned to meet up again a couple weeks later.
Julia: I understand why Aaron was picked for me. He had some traits I asked for — he identified as liberal and liked reading tech news, going to EDM concerts, and surfing, which I suppose could fit under "well-read," "likes art," and "is willing to lightly jog with me."
But more importantly, he was guaranteed to be normal, to not be blatantly rude or do anything to creep me out. I feel like women have to worry about two levels of comfort when it comes to dating — do you feel safe as a woman (does he refer to his exes as "bitches" and "sluts"?) and do you feel safe being yourself (do you feel comfortable being your goofy, neurotic, true self without fear of judgment?). With a matchmaker, that first level felt taken care of, which was nice. At no point in the date did I feel anxious, aside from just having to endure my monthly quota of small talk. And although I don't think you can really know anyone after just two hours, I feel like I could say he was a nice person and could be a good boyfriend, just to someone quite different from me.
I think you have to go into this accepting of the idea that the first date, even the first few, might be pretty off, because just two half-hour interview sessions with a matchmaker is not enough to get to know someone or understand what they specifically mean when they say they want someone "funny, smart, nice." You may have to sit through a few lukewarm evenings before you meet someone you're actually excited to talk to. As for me, I'd rather hang out with myself and leave fate a little more in my own hands, i.e., swiping through dating apps during Hulu ad breaks like the rest of us utterly hopeless, romantic weirdos.
Jarry: Three Day Rule may have done a good job matching me with Matt, but with Willy it seemed like they hadn't even tried — he had several of the traits I had explicitly said were deal breakers. And both were vetted by matchmakers I'd never met, which just seems like a bad game of telephone: How can you ensure compatibility if you've never even talked to the client you're trying to match?
Beyond this, the entire process wasn't exactly transparent: Julia and I were mostly in the dark about how TDR had found our specific matches and what they were told about us (not much, it seemed), so we had to ask them about it on the dates (all three had friends who were somehow connected to the matchmakers).
To be fair, a matchmaker has to know a client very well in order to successfully match him or her, and two half-hour sessions isn't enough time to accomplish that. But people regularly pay $5,000 just for three months of the service, which still doesn't seem like enough time, especially for that price. In many ways, Three Day Rule seems like a great concept with not-so-great execution: The process we experienced felt rushed and forced — two words I'd rather not have to use in the context of my love life.
Matt is 24 years old. An earlier version of this post misstated his age. Then again, Matt's real name isn't actually Matt, so no biggie.