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Episode Transcript: Love Help For Hire

This is “Dating While Gray: The Grown-up’s Guide to Love, Sex, and Relationships. I'm Laura Stassi.

Have you ever thought about paying someone to help you find a partner? On this episode, we're exploring love help for hire.

I was married for a long time to a do-it-yourselfer. So I'll use the analogy that dating is like a home- improvement project. It seems simple enough, and you've got the interest and the energy. So you decide to DIY. But after you get started, it doesn't go as smoothly as you thought it would. Maybe your skills are rusty, or your confidence is shaky. Maybe it's time to get some professional help.

CHERYL: 01:06
I realized that I need coaches. I really like coaches: I do boot camp. I've done nutrition coaches, I need that connection with one person to help guide me.

LAURA:  01:18
That's Cheryl, who's in her early 60s and divorced. In the year shortly after her split, Cheryl went online. But then she was introduced to a friend of a friend. They clicked romantically and were together for seven years.

CHERYL: 01:31
And then when that finished, I started trying to -- online dating again and ran into a lot of frustration. And so in 2020, a friend of mine told me about this dating coach that gave you a one session free and helped you with the online process.

LAURA:  01:53
You've expressed something that so many of us feel, which is you’re online, and it's not working. And some of us are wondering, why isn't this working? It looks like there's a whole bunch of people out there. What were your specific, I guess, disappointments or frustrations with online dating?

CHERYL: 02:13
I found that I just couldn't connect with men that I was interested in. Or we would have like days and days of talking on the phone, and then meeting in person and it just falling apart. And that's -- that's kind of the theme. Things would fall apart. And I just ran into men who assumed that I was after some information or that I -- I just was met with a lot of assumptions. There's one man who was mad at me for the questions I was asking. He just seemed to get upset because the questions were too general. Like I was saying, well just tell me more about yourself. Tell me about your personality. What would your friends say? Like, I don't know how to answer that. And then I've just -- one man. He lived out of town. I let him come to my house. And I said I'd love to spend some time, where do you live? Very suspicious about, you think that I'm married? You think that? I'm like, no, I just wanted to -- and we really connected. Personality wise, we were really good. But he was suspicious. That's what I've run into, some suspicions.

LAURA:  03:39
I mean, because when you're talking about somebody suspicious because you want to see where they live, I'm thinking, what are you hiding? So okay, so you heard from a friend who had found this dating coach?


LAURA: How did she find him, do you know?

CHERYL: 03:55
Yes, there was someone -- she lives in an apartment building. And a friend, a younger friend in the apartment building told her, because she knew that my friend was on Match and you know, looking; told her about her friend, this dating coach. He was doing this on the side. And so she met with them. She liked them. But she decided not to employ him. And so she told me about him. And then when I met him, I'm like, yes.

LAURA:  04:22
So this was just a natural, it seemed like it was a natural thing: I'm single; I want to be coupled. It's not working. Let me hire a coach. So you met with him? Was there like a fee immediately, or how did that …

CHERYL: 04:34
No, the first session was free. And then he required four sessions for very inexpensive, and then if I wanted to continue then I pay a little bit more and meet with him as much or as little as I wanted.

LAURA:  04:51
Okay, and so the four sessions -- without getting too much into your business. The first consultation was like a 30-minute consultation on an hour?

CHERYL: An hour consultation.

LAURA: For free. And then once you determined whether you had like good vibe with him or …


LAURA: Then he said, okay, this is how it works.


LAURA: And when you say very inexpensive, can you give me a range?

CHERYL:  05:11

Forty dollars per session …

LAURA: Okay.

CHERYL: For four. And then if you want to continue, $60 for an hour. He kind of gave me a roadmap. He said, I want to talk about these things, what you want out of a relationship, your past relationships, you know, where the tensions happen. And I could just talk and talk and talk. And then he would make connections: he would give me homework, I want you to write and think about these things. I want you to look at the past and where things might have gone wrong. I want you to talk about or look at what you want in this area -- sexuality, finances. So he really divided things up. And because he has a natural - because he's very insightful and intuitive, that he could lift up some patterns. And we would look at patterns.

LAURA:  06:07
Is there anything in particular you remember that it was like, oh, ah-ha! I never, if I hadn't hired a dating coach, I never would have blah.

CHERYL: 06:17
Yeah, he pointed out that I can tend to get really connected based on words, based on what the man that I'm, you know, potentially dating, what he said. And he said, you look, you need to look more at actions. And that helped me, you know, in my life period. But, you know, we started calling them pretty words. Like if men have pretty words, then you just, say, get me boiled over and get connected emotionally, where there's not a connection yet. And you need to look more at their actions. And I mean, other people have said that, but when he put it to particular people that I was trying to date, it made perfect sense. And it clicked.

LAURA:  07:10
Yeah. Interesting. And I think so this dating coach, it's not like he's finding new people for you to date.


LAURA: He's just guiding you through, basically, online dating? Or …

CHERYL: 07:20
And he also said, you know, Cheryl, if you're out and you see somebody that you want to talk to, but you don't quite know what to say, text me, I'll tell you what to say.


CHERYL:, Yeah. So he was like on call, he was an on-line coach.

You know, I've run into love bombers I've run into sex addicts, have run into … and it's been disappointing. There's been some fun, but generally speaking, I feel like this is not for me. And I know, you know, other women will come to that point, stop and take a break. And, you know, even the coach said, you know, you can take a break and it's okay.

LAURA:  08:08
Okay. Some people might say, well, you hired a coach. You spent money and still, nothing happened. So what would you say to something like that?

CHERYL: 08:16
Oh, I would say plenty happened. Plenty happened. The experience was a treasure for me. And I learned things about myself that I really need for my journey. And not that, you know, oh, gosh, I didn't know this about me. Some things I knew. But some things I've found acceptance of and naming something: Cheryl, you're the kind of person who blah, blah, blah, or, you know, it just so helpful. And that's information. I need emotional support. That, I needed. It was worth every penny.

LAURA:  08:58
So Cheryl was not lucky in love, despite hiring a dating coach. But you heard her. She has no regrets. And she told me if she's ever ready to get back online or to make a more focused effort on her love life, she'll turn to the coach again.

You know, some people decide they want more than a coach, more than someone to guide them on the dating journey. Some people decide to put their entire love search into the hands of a pro.

What really appealed to me about the matchmaker, he was a hands-on kind of guy, you know, he used his intuition, his Dolly Levi acumen. And he had a couple of theories, but one of them was that we don't always know what we're looking for.

LAURA:  09:42
That’s Steven, and he hired a matchmaker. We'll talk about it next.

Steven Petrow is a journalist and author in his 60s. His latest book is called “Stupid Things I Won't Do When I Get Old.” One of the things he writes about is telling the truth about his age. When I talked with Steven during Season 1, he admitted that he shaved off a few years on dating apps.


STEVEN: 10:13
How old am I in real life or how old am I online?

LAURA:  10:18


LAURA: Yup, Steven’s been online. But he found his longtime partner through a matchmaker. And this matchmaker had a really personal approach to his job.

STEVEN:  10:29
He would come on each of the first dates. And so when it was going well and the two of us were talking, he would just kind of sit back and let it go. But when it wasn't going well, he would do some prompts to try to flush out common ground, common stories. And then afterwards, you would get a dating critique. So for instance, you know, if I had been tired that day, which all of us can be, if you -- say your energy level was low, or you really didn't make eye contact, you never used his name, things like that, that we, you know, we might not realize ourselves. So it was very helpful in in a practical and tactical way, and definitely weird having a third party at the table.

LAURA:  11:12
Yeah, but you know, that's interesting, because I haven't heard that. They're actually coming with you, because it's almost like a, like you said, a post -- kind of coaching session or a download of exactly what they observed. And as we know, sometimes somebody might be good for us. But because of, I don't know, how we're feeling that day, or nerves or something like that, we might not feel like there's a connection.

STEVEN: 11:34
Or we might not be our best selves on a particular day. And that certainly happens. And so I remember a couple of times sooner, he encouraged me to do another date, because he felt my attention or energy had not been there.

LAURA:  11:49
Yeah. Now, you mentioned the cost.

STEVEN: Mm-hmm.

LAURA: Did this matchmaker -- and I know that this matchmaker sounds like he had a pool of people that he introduced you to. Was that the only kind of service he offered? Because I've also heard of people who will, like, go out and search for you. But of course, that's a more expensive service.

STEVEN: 12:09
He had a pool, a pre-existing pool. And so he used that. And part of the fee – or, the fee was really meant to include what he called 10 matching opportunities, 10 first dates, and kind of -- you kind of go through them. And then if you renewed for the next year, but at a lesser rate, you got X more. I don't quite remember what that was at this point. So when I signed up, it was $6,000. And that was in 2002, or 2003.

LAURA:  12:38
And you're saying he guaranteed you a certain number of dates, but not a time limit or …

STEVEN: 12:42
Within the year.

LAURA: Within the year. Okay. And it worked for you.

STEVEN: 12:47
It worked for me. I think I was in -- I had been in the program for -- I was in my second year when I met Jim. And so I'd gotten a full 10. And then I was getting a second complement. Jim and I are no longer together, but that's no fault of the matchmaker. But I was the first person that Jim was introduced to so he always liked to joke that he didn't get his full money's worth of dating opportunities. He got me. And when we were happy together, that was funny.

LAURA:  13:16
Yeah. So yeah, I was gonna say so y'all got divorced. And now you're working with a matchmaker again.

STEVEN: 13:22
So when we talked, I was working with a different matchmaker. This was pre-COVID. I do remember that. And I didn't find that -- I didn't, I didn't really like that service. When I was working with Dale, you would be—he had a master book. So you would see photographs of the potential date. And I remember he came and did a photo shoot of me. Oh, you know, there was kind of a whole lot of information. So you had a real sense of many attributes. With this other one, she was really asking that you trust her. And she would tell you maybe three sentences, and there were no photographs. And so I did kind of the introductory part, but I didn't pay the fee, which I believe was $20,000 a year. And this was two or three years ago. So that -- I needed more disclosure to go forward.

LAURA:  14:15
Yeah. So it does strike me that first of all, one needs to have some disposable income of some amount to invest in a matchmaker.

Absolutely. You know, I feel sort of uncomfortable talking about these numbers because clearly, they represent some privilege, which, you know, I was fortunate to have. I remember, especially that in the first instance, Dale made the argument, you hire a lawyer when you need legal services. You hire a plumber, you hire an electrician, you hire an accountant. So why would you not hire a matchmaker for something that you consider important to your life? And that was I thought a very good argument. I generally didn't spend that kind of money on any of those other professional services, but I did -- the point made sense to me.

LAURA:  15:01
For somebody who's thinking about, maybe I should hire a matchmaker, what would be some of your tips that you could offer?

That's a great question. So I think the first thing I would suggest, which I did in both cases, which is ask for references, and talk to them. They will explain how the service works that you should find out from from people who have been involved, did it really work out that way? Were they satisfied? How are these individuals vetted? You know, one hopes slash assumes that they're vetted in ways that really matter and perhaps with background checks, and so on. Because when you're using the apps, it's kind of a wild and crazy world out there, whether somebody is even who they pretend to be.

And then also think whether you have a sense of that person understanding you and hearing what you want out of out of a partner. I think that two-way communication really matters as then they think about who's going to be the right person for you. One of the things I really did like about the first matchmaker was that he personally knew each of the people in his stable of folks, and had done extensive interviews with them and background checks. So there was kind of that firsthand knowledge, which mattered to me a lot.

The second matchmaker who was a woman, she only matched gay men.


STEVEN: That was that was her superpower. I mean, I will say she did something -- and I think she did this for me because I was a journalist, not that she did this for all of our clients. But she gave me one free match. So I didn't have to join.

And what was interesting about that, and what I learned from it was, I was on vacation in Rhode Island, and she matched me with someone from Boston. And on paper, we were very good match. He was a professional, he was age appropriate. But as I said, I didn't get a visual of him beforehand. Which also includes not, you know, you never know what chemistry is going to be with somebody. So we had, we had dinner. He was a delightful person. There, there was no real magic. We went on a second date.

LAURA: Oh, you gave him a second chance.

STEVEN: I wanted him to give a second chance.

LAURA : Yeah.

STEVEN: Yes. You know, because I had learned something from the first time and I thought, well, who knows. And he was game for a second chance. So he flew down to Washington, D.C., from Boston; I flew up from North Carolina. And we met, and we had a second dinner.

And he went to a great deal of effort to make it lovely, and it was lovely. But there still wasn't really that, that energy. And so we both moved on from that. But that was kind of telling to me, that you do need some sense of whether it's the physicality or the emotionality, so many -- because you can read so much into a person's face too and someone's eyes. Like, you know, I really appreciate even though we're doing a podcast, I can see your face. I see your eyes, they are warm, they are inviting. You're not wearing a mask, you have a very nice smile. And you have -- and this -- and you have really good dental hygiene, which really matters to me. And I don't know how to find that out ahead of time.


LAURA:  18:23
Yeah, it’s hard. So the second matchmaker, you just decided not to go down the road with after just one experience? Did you just feel like was she very so adamant about that not looking ahead of time that …

STEVEN: 18:35
That was definitely one of the rules. And then the other aspect was, you know, she had comped me that one, but then I would have had to pay full freight. And there were no matches in my state. So, you know, there were people – one was in Boston, there was another one, I think, in Ann Arbor. And what she said to me was, you know, these are people who have means, who were maybe retired or semiretired and who, you know, have the ability to be mobile, obviously before COVID. But that was kind of a limiting thing to me, too. After meeting the second time and both of us flying into a different city, I become less enthusiastic about longer distance relationships.

LAURA:  19:15
How about any warning signs. If somebody is looking for a matchmaker, what is something that they should you know, total red flag, pick somebody else?

STEVEN: 19:25
I would say, if somebody told me they were going to, they could guarantee they could find me the love of my life or the love for the next five years. I would say that's bull----. Because nobody can guarantee such a thing.

LAURA:  19:46
Like Steven said, when it comes to love, there are no guarantees -- even when we're paying someone to find it for us, even when we're paying a lot. And make no mistake: Love help for hire is a big-buck business. I wanted to hear about the business side of things. So I talked to two people who are romance professionals. That's next.

My name is Jolene Beaton. I am a date coach and matchmaker with It's Just Lunch. And I've been with the company for 14 years now. So matchmaking services, there's a variety of different types. But the idea is that you're going to get to a date, you're going to cut out a lot of the going back and forth on let's say, or, or just going to the gym and trying to find someone or through friends, you know. It really cuts out a lot of time. And you get straight to sitting across from someone, and you can decide. And you're just having a conversation.

So with matchmaking services, typically they'll do an interview where they'll find out, who are you? What's your belief system about dating, your philosophy about love and relationships? What do you want to create? And how can we put you in front of single people that are serious about also dating? That doesn't necessarily mean they're all on the same page of, I need to get married right away. Or, I mean, there's plenty of people that say, I don't really need to get married. I definitely want monogamy. The majority of people want long term, committed monogamy.

LAURA:  21:37
So someone comes to you, let's say I come to you and say I want to hire you. You said that you would interview me to get an idea of what I'm looking for. Do you do any other kind of screening? Like, will you run a credit report on me or do a background check? What kind of screening is involved?

JOLENE 21:54
So we do not do background checks or credit reports at all. We do a face-to-face interview, we'll do a phone interview, we'll determine if you are a good fit for our clients, if you could be successful here. And then if you are, we'll give it a go. So we have a traditional service, which is come join our social club It's a targeted approach; you will get on real dates with real people. And you could get to the yes or the no very quickly. Right? Then we have a higher price point service, is where you can tell us your ideal and we will go out and find it.

LAURA:  22:32
OK. And so somebody comes and joins your pool. And you say that you set them up face to face. Do you guarantee a certain number of people or, how does that work? Or is it a time limit?

JOLENE 22:48
Our memberships, they range typically, you could do like a six-month membership and you're guaranteed a minimum of six dates. We always try to under promise and over deliver. It depends on what you're looking for and how specific you are. Some people are like, I'm open, I want to meet everybody you guys got; I’ll be the decision maker. You know, you just set me up. And others are, they're not interested in spending time on someone that they know is not going to be a great fit.

So you know, it just depends on how narrow someone's parameters are. And we try to work with both, because we do believe that dating just in itself is valuable. So even if you're not meeting, you know -- be certain on what you want to create in a relationship and go for it, you know, get the greatest relationship possible, you know. But the dating, we’re usually saying just be open with that. Because when you're out connecting, you are making things happen, you know. And I'll I tell my clients, you need to get value out of this, whether or not you end up in a relationship. You need to unattach from the idea that there's some perfect person, or dating is some perfect thing. And you just need to get into it that you're just meeting new people. And people are fascinating, and they're interesting, and they want to be there. And that is where the value is because anytime that we connect with someone, it is changing our chemistry. It has the power to open our hearts and that's, I think that's the name of the game.

It's interesting, I find that my clients, you know, they expect modern dating to be one way and it's because a lot of horror stories and there's a ton of scam artists out there, and it's really, really terrible. But there are so many incredible people out there and so, you know, hiring a service -- I do think it just educates you and connects you

LAURA:  24:55
Jolene is based on the West Coast. It's Just Lunch is available in several cities across the US. Now let's hear about another love business that also has a national presence, but a different operating model.

My name is Stacy Blackwell, and I am one of the matchmakers at VIDA Select, which is an online dating matchmaking service. We completely manage and take care of your online dating presence.

LAURA: Okay.

STACY: So we find matches for you. All that we come to you for is for approval of potential matches. And then to deliver you the phone number or the date depending on what you've pre-arranged with your matchmaker.

LAURA:  25:49
You know, I'm thinking people are -- will think it's nice to have an extra set of eyes looking online for me, because, you know, everybody knows online is a time suck. But once you identify two or three potential romantic partners for me, how would you vet them before passing them on to me? Or do you do that?

STACY: 26:08
Through conversation.

LAURA:  26:12
Are you that person online, is it like Cyran -- what was that ...

STACY: Cyrano de Bergerac?

LAURA: Cyrano de Bergerac, yeah. Is it like that?

STACY: Mm-hmm.

LAURA: Okay, this is fascinating to me. This is eye-opening. So you are basically me online. Because I might look a certain way, but I don't -- I'm a -- as you can see, I'm stuttering and stumbling now, I'm not good at on the spot. Okay.

STACY 26:44
Clients that come to VIDA, they come to us because they are busy, and they don't have the time it -- you know, in order to do online dating, well, it can be like a part-time job sometimes. And sometimes people don't have the space to do that, or they don't have the desire to do that. Or maybe they don't have the skill to do it, do it well.

You know, marketing yourself in a genuinely attractive way is a learned skill. And that's not something people are naturally good at. We find the potential matches on online dating sites, right, using your information. But we go out and we look for the potential matches, we screen the potential matches. When we find someone that has a return interest, then we will reach out to you for approval.

I always kind of align online dating with fishing. And when you want to go fishing, you want to be in a big pool with a lot of fish, you know? And so online dating is the big pool. And depending on which platform you're going to select is going to determine how many potential matches are in there for you. You know, online dating conversations, they're not meant to learn someone's deep, dark secrets. They're not designed to go from there into a book form as your biography, you know. It's a way to break the ice with someone, to kind of feel them out and see if they're date-worthy. Because getting face to face, that's where you're gonna see the chemistry. That's where you're gonna feel the chemistry or, in a situation like this video dating, that's when you're going to have more of the connection. So we take care of that initial.

But we are very cautious and put forth great effort to represent the client as authentically as we can because we don't want them to go to the date or to the phone call and the person on the other end being like, who are you? Like, that would be self-defeating because we want our clients to have success.

LAURA:  29:09
Okay, so all you 19th century French drama majors? I see you. You know Cyrano de Bergerac is not a pure comparison. Cyrano believed his unusually large nose made him an unsuitable suitor. So he hid his identity as the author of the love letters to the beautiful Roxanne. But you get the point. Some of us reach the conclusion that when it comes to finding a romantic partner, we need help.

And for a price, there are all kinds of services out there willing to help us, either one on one or as a group: coaching, matchmaking, hybrid models that combine the two. And by the way, there's no requirement for professional certification, which means anyone can call themselves a dating coach or a matchmaker.

So I recommend doing research before hiring any love help. Understand what you're getting, how much you're paying, and for how long you're obligated. Because this is a business deal. Just like romantic love, you want the relationship to be successful. And you don't want to be left with disappointments and regrets.

Dating While Gray is produced in partnership with WUNC North Carolina Public Radio. Our producer is Anisa Khalifa. Charlie Shelton-Ormond is our editor. Lindsay Foster Thomas is WUNC’s director of content. And Jenni Lawson is our audio engineer.

I'm Laura Stassi. If you have a question or comment, email And now you can also leave me a voicemail. Go to and at the top right, click on “Talk to Us.”

I'd love to hear from you. And thanks for listening.