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Dating Expert Courteney Kay Reveals New Matchmaking Site Single Angelenos Need to Use – and Why Companies Like Grouper Fail to Succeed

November 5, 2014

courteneykayAnother day, another development to help us poor, single Angelenos find true love. But while the likes of Tinder and Hinge are much more casual, Dating Ring, a New York and San Francisco-based site that just became available in Los Angeles and Boston, provides in-depth curated matches for its customers by actual certified matchmakers.

I recently chatted with courting expert (and Dating Ring CA Regional Coordinator and Executive Matchmaker) Courteney Kay, a USC grad-turned-SF-resident who has been working in the dating field for as long as she can remember. Courteney, who was inspired after meeting her fiance years ago on, tells skyelyfe she’s “always been a human connector type who would throw parties and introduce people.”

Getting her start producing dating events in Orange County, Courteney eventually moved up north, where she began working at Grouper (more on that below).

The lucky-in-love lady shares her excitement about Dating Ring’s L.A. launch and notes that a big selling point right now is the one month free that new users get.

Read on for more about this exciting new tool, Courteney’s fascinating career journey to where she is now and what her thoughts are on other online dating sites and apps:

SL: So, how exactly does the matching work on Dating Ring?

CK: Users get matches sent to them either once a month or four times a month depending on which subscription plan they sign up for. Paid users take priority in matching, but there is also a free option which sends out some matches, but is not as consistent or guaranteed. Every user has a matchmaker who actually reviews all of the matches and will say yes or no to send them out and basically give a little note out about why they’re sending them as a match. The notes will say something like, “Hey, I just want to let you know that I wanted to match you up with Joe because you guys both have a love of organic food and yoga and both love to read and attend personal development conferences.” You’ll be able to see the others user’s photos and basic demographic information such as height and age. With each match, it’ll give the user the opportunity to send the matchmaker feedback. It’s kind of like the anti-Tinder in the sense that there’s a lot more behind-the-scenes going on with the actual matching and compatibility.

SL: Once a first-time user’s free month is up, what’s next?

CK: You get one match per week on a paid subscription and the pricing varies depending on if you go month-to-month or sign up for a longer 3-month or 6-month package. It’s similar to how other online dating sites do it.

It’s $60/month for one matchmaker-curated match per week if you’re month-to-month, $40/month if you’re on a three-month package or $30/month if you’re on a six-month package.

It’s a similar price point to an actual online dating site, but in this case, the matchmakers are able to curate the experience and it’s a lot less of that whole cat and mouse game and browsing through profiles. It’s more about quality over quantity and simplifying your life!

SL: What was your experience like working at Grouper? I went on a few of those dates with friends and we ended up with the most bizarre matches!

CK: Grouper had a lot of issues. Either they’re totally done or they’ve very much declined. The way they did matching wasn’t super [effective]. I don’t think they focused a lot on the actual matching. People wanted to try it out, but once you have those first one or two drink dates that don’t provide much value for you, people are pretty over it. When I was working there, it was pretty obvious that something needed to be done about the matching to improve things. There were plans to do so, but it took a lot longer to get going than I expected.

It was really heavy on the marketing. When people would sign up for a certain night on Grouper under the guise of a great match, it would be like everyone who signed up for that night would get funneled into one night and then the best possible match would be picked from there. The filtering or curating of the matches didn’t start as early as it should have been. Also, it was very hard for us to know what the wing-women or men were going to be like and who was actually going to show up, since this information was often not completed by the user or changed around last minute. So, sometimes you’d have like a 35-year-old with a 25-year-old. You can see how it could get all sorts of crazy and that made it difficult to keep everyone happy.

SL: What are your thoughts on some of the other blind dating avenues?

CK: I think OKCupid has done one of the best jobs as far as algorithm and really getting to know its users and stuff like that, but the problem is there is no real barrier to entry. There’s just everything. It isn’t super curated, so it can get a little bit spammy as a girl. You get so many messages from so many people and a lot of them you’re just like, “No way!” The nice thing about paid sites is it kind of ups the quality bar. Tinder is obviously huge, but it doesn’t really give you any insight to someone. We just feel like you need to have a little bit more to go off of before you go on a date with someone.

SL: What happens when you have a client with really high standards or someone who really can’t seem to match up with anyone?

CK: A lot of the work is not just the matchmaking. There’s a lot of coaching involved. A huge part is telling someone what their expectations should be like, and basically being able to relay how realistic those are. When people want a more tailored and customized coaching and matchmaking experience, that is when we have them try out our premium matchmaking service only available in New York and San Francisco at this time.

SL: The matchmaking field sounds so fun and interesting. How does a person land such a career?

CK: The best way to start working in the dating space is to demonstrate you have a passion for it because the hours can be long and it’s definitely a certain skill you have to have. For me, it kind of started with doing online dating management and helping with peoples’ photos and that kind of stuff. And then it kind of carried over into running a community and hosting speed dating events for a year. Then I started my own singles events in Orange County. And then I started working with Grouper and then Dating Ring. I also wrote dating advice for a website called Made Woman magazine, so I kind of think all of those experiences led people to be like, “Okay, this girl really wants to work in this space.” There’s no school for it.


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