When Dating Felt Like A Job, One Woman Hired A Matchmaker Kat McClain describes herself as a long-time dating app user, but it eventually felt like a grind. Frustrated by the process, she hired a matchmaker who helped vet dates and up her online dating game.

When Dating Felt Like A Job, One Woman Hired A Matchmaker

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And we have an update now on a series we have been doing all this month. It is about online dating. And Rachel, I know that's something you know a thing or two about.


Little bit - it's true. I met my husband online in 2009 - way back in the olden days (laughter).

GREENE: Not so far back, 2009. But, you know, things have changed since then. Online dating has become a lot more common.

MARTIN: Right.

GREENE: I was stunned by this number. Some 100 million people have downloaded the Tinder app. But, you know, this whole thing can be pretty frustrating.

MARTIN: Totally. I mean, I was in the trenches, man. And it can be hard and disheartening. There are all kinds of profile pictures. We've heard about that. It's not really what the people look like. And then there's just, you know, disaster dates and people who don't show up - whatever. There are a lot of horror stories, but it can work out.

GREENE: Yeah. But you're not alone with the horror stories. People are exhausted. They're discouraged by the process. And that was the case for Kat McClain.

KAT MCCLAIN: I was going out a lot. I was getting burnt out. I was bored. It felt like another job, and I definitely don't need another job. I work enough (laughter).

GREENE: So Kat's a 26-year-old attorney here in LA. She describes herself as this meticulous planner. She's a former gymnast She's a die-hard sports fan, and she's also a longtime user of those dating apps.

MCCLAIN: But I was feeling like there was something wrong with me. You know, I was the only person that I knew who wasn't in a successful relationship. And everyone around me was making it work. And I was like, what am I doing wrong? Like, why? Why does this keep happening to me?

GREENE: So she decided that she was going to enlist some help. She hired a matchmaker.

MARTIN: A matchmaker? Like, "Fiddler On The Roof" - like a yenta matchmaker?

GREENE: I mean, not exactly. But she went to a company. It's called Three Day Rule. And let's tag along for her journey. And this journey is going to include a first date - we'll get to that a bit later - but first, a little bit more about Three Day Rule.

TALIA GOLDSTEIN: So when I started the company, actually it was just a blog. And I took the name from "Swingers," the movie. It's this old stupid rule that guys used to wait three days to call a girl after getting her number.

GREENE: So I was sitting talking to Talia Goldstein - she's the founder of Three Day Rule - and she says that the rules for finding a date have totally changed. We were talking at the company's high-rise office in LA.

GOLDSTEIN: We find matches in all different ways. If our client is interested in a corporate guy, we're crashing real estate conferences and medical conferences.

GREENE: They have a database also of 90,000 single people. And of course, all of that access does not come cheap.

MCCLAIN: Six thousand?

MARTIN: Six thousand bucks?

GREENE: Six thousand dollars.


GREENE: That was Kat there. Yeah, she was telling you how much she pays to use this service, Three Day Rule. And from that money, what you get is you get 6 dates over a six-month period. And you also get this personalized matchmaker.

MCCLAIN: I was really at ease. Like, one of the first things I noticed was just how easy it was to talk to her.

GREENE: So Kat's talking about her matchmaker, Alexa Geistman. And when I met up with the two of them in the company's conference room, Alexa had already spent a couple of months just getting to know Kat.

ALEXA GEISTMAN: We have a very close relationship. So we do talk quite a bit, a few times a week.

MCCLAIN: Having someone like Alexa around to keep me positive and centered and grounded has been - I mean, life-changing sounds so dramatic but life-changing.

GREENE: Kat was looking for a relationship. And so Alexa told her to search on all fronts, including dating apps.

MCCLAIN: I also changed all of my profiles from bottom to top - the pictures, the bio, the, like, what-are-you-looking-for section. So it's been a really different dating app experience.

MARTIN: So then, Kat does this whole, like, overhaul of her profile. And what happened? Did it work for her?

GREENE: I mean, it kind of worked. She didn't have a single bad date with an online match after that.

MCCLAIN: I would say that I'm a better online dater for having done this. And I am just - I'm better at picking people. I'm better at presenting myself accurately.

GREENE: So she meets the love of her life on a totally different site - you're not going to feel like that was somehow a failure?

GEISTMAN: Absolutely not. I mean, I might attribute some of the success to me because I've really helped her become an even better dater.

GREENE: But she still hadn't found anyone serious yet.

GEISTMAN: I think she needs someone with a quiet confidence that shares the same values as her.

GREENE: All right. And that is where Kevin comes in. He was a guy in Three Day Rules' database. Alexa had introduced him to Kat over email, and they were getting ready to go out that night.

How are you feeling about tonight?

MCCLAIN: I'm excited. So my goals for tonight are, like, drink slow, ask questions, do not put on a show. Like, don't start your, like, Kat stand-up routine. Because I do have this, like, habit of just starting to tell rapid-fire, self-deprecating jokes when I get nervous.

GREENE: So Kat met Kevin at this restaurant in LA. Both of them were clearly a little nervous at the beginning.


MCCLAIN: Yes. Hi. Sorry.

GREENE: And Rachel, it probably did not help that we had put microphones on the table (laughter).

MARTIN: Right, no pressure.

GREENE: Yeah, no pressure. But they were really good sports.

MCCLAIN: I bet you at least a few people here think we're famous.

BIELY: Exactly. Right?


BIELY: Someone's, like, Googling me. Like...

GREENE: All right, a little awkward at the beginning - but the conversation got going, and it was constant. And you could really hear the chemistry. They learned they had similar upbringings....

BIELY: So I grew up with a military family, so we bounced around a little bit when I was young.

MCCLAIN: Yeah, yeah. I am also a military brat.

BIELY: Oh, nice.

GREENE: ...Also a similar sense of humor about who their ideal partner might be.

BIELY: If she's got a job and she chews with her mouth closed, that's like 90th percentile right there.

MCCLAIN: That's sounds stunningly like my criteria.

GREENE: Oh, my God. I'm, like, uncomfortable listening to their first date.

MARTIN: I know. Me, too. First date (groaning).

GREENE: It's so uncomfortable. But it went well. They talked so long they actually closed out the restaurant - after dessert, of course.

MCCLAIN: I could do the sundae.

BIELY: Awesome.

MCCLAIN: Half the sundae.

BIELY: Half the sundae. Half a sundae?


BIELY: What will we do with the other half?

MCCLAIN: You should have the other half.

BIELY: Maybe I'll have it. OK. Fair enough.

MCCLAIN: (Laughter).


GREENE: OK. So about a month and a half after that first date, I caught up with Kat on the phone.


GREENE: Hey, Kat.


GREENE: So how are things going?

MCCLAIN: Things are really great. Literally just a couple of days ago, we had to define-the-relationship conversation. So...

GREENE: Whoa. Kat says even though her Three Day Rule experience with this company made this possible, none of the rules seemed to matter anymore.

MCCLAIN: It didn't matter that we talked about marriage on the first date. And it didn't matter that I told a bunch of stupid jokes. And it didn't matter who texted who first afterwards. None of that stuff is important. Sometimes stuff just works.

MARTIN: So it worked for her, huh?

GREENE: It did work out for her. And - I mean, she said sometimes stuff just works. So yeah, she deleted her dating apps. Now she and Kevin Biely are dating exclusively. It was really nice to hear that.

MARTIN: Yeah, but she paid a ton of money. Does she have any regrets about that?

GREENE: She did pay a ton of money. And she said that she doesn't regret that at all because - I mean, this company brought her to Kevin. And it also - she said the coaching gave her this better overall outlook on dating. And Kat said not everyone needs to hire a matchmaker. You don't have to go out and spend this money. You can. It can help. But at the end of the day, no matter what you do, it really still comes down to chemistry.


NEVA SMALL: (As Chava, singing) Matchmaker, matchmaker, I'll bring the veil.

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