Professional Matchmaking: How Real Introductions Beat The Apps #119

Looking for love without the burnout? We sit down with Cheryl Maida, Director of Matchmaking at Matchmaking.com, to explore how high-quality, values-driven introductions can replace endless swiping with genuine connection. Cheryl has spent nearly 16 years guiding singles through a noisy dating landscape, and she lays out a clear path from fatigue to fit: fewer introductions, deeper screening, and coaching that helps you focus on what actually sustains a relationship.

We dig into the real tradeoffs between dating apps and professional matchmaking: speed and volume versus trust and compatibility. Cheryl explains how her team interviews every client, screens for core values, life goals, and personality, and crafts concise bios that go beyond photos. You’ll hear why long checklists sabotage momentum, how to narrow to your three or four non-negotiables, and what happens when you challenge assumptions about age and body type. Her story about revealing age last—after interest sparks from substance—shows how often we’re drawn to energy and lifestyle over a number.

The conversation also tackles the modern mess: scams, ghosting, and even AI-generated profiles that make it harder to trust what you see. Cheryl shares practical ways to meet people offline with intention plus small social habits that make you more approachable. We cover who can join her database, why women are free and men are clients, the firm boundaries she holds with misaligned expectations, and the expanding niches her team supports, including a fast-growing community of gay men and professionals across the country.

If you want a smarter strategy for dating—one built on clarity, compatibility, and credible introductions—this conversation offers a hopeful reset. Subscribe, share with a friend who’s swiped out, and leave a review to tell us which dating “rule” you’re ready to rethink. Then, if you’re curious about curated matches, visit matchmaking.com to connect with Cheryl’s team.

Chapters

• 0:00 Welcome And Guest Introduction
• 0:25 From Apps To Matchmaking
• 1:23 Defining Compatibility Beyond Checklists
• 4:40 Nudging Clients Past Biases
• 6:12 The Age Debate And Energy Fit
• 8:28 Body Image, Fitness, And Realistic Expectations
• 10:56 Turning Down Misaligned Clients
• 14:07 How Matchmakers Prioritize Paying Clients
• 14:58 Meeting People Offline With Intention
• 17:58 App Fatigue, Scams, And AI Profiles
• 19:27 Who Can Join The Database
• 20:26 Expanding Niches And Professional Focus
• 21:30 Success Stories Across All Ages
• 22:29 Success Rates And Client Outcomes
• 23:07 Closing Thoughts And Calls To Action

Transcript

Intro: 0:00

Welcome to the Straight from the Source's Mouth Podcast. Frank talk about sex and dating.

Tamara: 0:06

Hello, Tamara here. Welcome to the show. Today's guest is Cheryl Maida, Director of Matchmaking at matchmaking.com. And we'll be talking about what it takes to date and forge connection in today's fast-moving world and the real value of meaningful introductions. Thanks for joining me, Cheryl.

Cheryl: 0:22

Hi, Tamara. It's so nice to meet you. So happy to be here.

Tamara: 0:25

Yes, I think this there's a lot of dating fatigue, a lot of people getting sick of it. So what would you say are the benefits to being like matched versus, you know, like through a personal, more personal things approach?

Cheryl: 0:38

Yeah. So there's so many benefits. You know, I always start off. I I've been a matchmaker for a little, almost 16 years now. And when I started almost 16 years ago, it was amazing because the apps were just coming out. So I always laugh when I think back then, people were like embarrassed to admit they were on an app. Like you kept that very private. Now it's very unusual to speak to someone who's single who's never tried it. Um clearly, there's pluses and minuses of everything, right? I never bash anything. Um, in regard to the apps, what were the pluses? Listen, convenience, you could lie on your bed and scroll through people, quantity, um, definitely hundreds of thousands of people to choose from. And it was very quick. If you wanted to meet someone, it was probably a quicker avenue. But at the end of the day, and this is what I've heard again, especially in the last 10 years or so, you're not getting the quality. You're not finding the quality you would than if you went to a matchmaker because matchmaking is very different. So, in other words, we're not just throwing out a hundred different people to you and let's see which one sticks. No, we are interviewing every single client. We are getting to know them. We are building a relationship with them. We are asking very important questions that has to do with matching people up. And we could use something for an example, like, where are you from? Where do you live? Your age range, is religion important? Is political view important? What someone's profession is? I think a very big one is what are you looking to do? Are you looking to get married and have a family? Do you have a family? Um, hobbies. Sometimes people, the most important things are hobbies. Maybe they're just about to be retired or they want to travel now for the next few years. So, us as matchmakers, we get to ask those very detailed questions. And based on someone's answer, are we looking to really find someone truly compatible? Um, the matchmaker also presents members to our so clients are the people that pay us, members are the free individuals in the database. And so when we present members, we are giving a bio, we are showing photos, but we are talking about the person. You see, this is what the apps you can't do, right? It's almost like when you get a resume for a job versus meeting someone in person. I don't feel that. How can you tell from looking at a picture on an app, wow, I could see if I'll have a connection with this person? You can't. It's so different. So it really depends on what you are looking for, what is your end goal? Did you just get divorced and you're looking to just date because you've been married for 30 years? Or are you ready to settle down? And if someone's ready for a serious relationship, whether or not they want to get married, matchmaking is really the route to go for that reason.

Tamara: 3:23

Yeah. And I know you said you talked to them about a lot, all the stuff about them. Do you also talk about like the other compatibility stuff like core values and that kind of stuff? Or personality or absolutely.

Cheryl: 3:34

And that's very important too. So the first initial part of my interview is always like the things I had just mentioned, right? And then the second part is now I want to know what are you looking for? And we start off personality. Are you looking for someone more extroverted, someone a little more introverted? Do you want type A personality, type B? Um, do I come to aesthetics? I do. At the end, I'll I will say, do you have a look you like? Listen, some people prefer taller, shorter, brunette, blonde, all different types. Um, but at the end of the day, you know, I think, I think the most important thing, as you said, values, core values, what is the most important to you? Because as I said, we have checklists, we all do. And everyone that comes into me has these checklists of what they're looking for. I always say if you have a checklist of 10 things, do not think you're gonna check everything off. Because if you do, you're gonna be single for quite a while. Think to yourself, what is the three, maybe four most important things to you? And if we check those things off, that's someone you should be very open-minded to meeting.

Tamara: 4:39

Yeah, yeah, definitely. And are there some where people say they want a certain thing and then you realize that it's probably not like best for them? Or do you let give them what they want?

Cheryl: 4:48

And definitely, definitely. I think in the beginning, I always tell my matchmakers, be a very good listener. I want to respect the person. I don't know them yet. I want to respect their answers because look, this is what they're saying is the most important. But sometimes if a man will come in, and again, if they say, you know, the figure, the body image, that's the most important thing to them. Okay, I will write that down. But I know at the end of the day, if I find a phenomenal woman who checks off the most important things, and if she's not this perfect body, okay, I know that is something I could talk about with the client and he will meet them. I never push anyone to meet someone, but I do, it's almost like therapy. We try to open it up into a bigger topic and say, let's talk about this person. What is the worst case scenario, right? You meet for a drink, a lunch, or a dinner, you walk away. I have never in 16 years had someone say they have went on an awful date. The worst case scenario is maybe they didn't feel the chemistry, but a lot of times when we gave that extra push, like what you had just asked me, like, okay, just please meet her. I think you're gonna like her. You'd be amazed at how many times people come back. I am so happy you told me to go out with him or her. That was one of the best dates I've ever had. So sometimes we do have to give like a little push if we really feel in our heart of hearts, it might be a great match.

Tamara: 6:11

Yeah. Yeah, I was I mentioned before the show quickly that I I was in the database before, like years earlier, and I was matched with a couple guys, but I've always dated younger, like that is just my preference. And I told them, so they matched me with someone older who was interested, and like I just couldn't do. I mean, I we had a good date, I'm sure he thought it was too like it was enjoyable enough.

Cheryl: 6:34

Right. But now, did you not did you not move forward because he wasn't younger? Were there other things that you didn't like?

Tamara: 6:41

I mean, it's probably shallow to say, but it was mostly because he was older. I mean, he was very established, and a lot of people probably would see him as you know, it just well, he also had like his kids, he wasn't necessarily in great communication with his kids and kind of had some drama there. So that may have been part of it too.

Cheryl: 6:59

Age is a big thing. You know, it's interesting. I always say I don't believe in age, I really don't. Um, I think, like, let's say, for an example, someone wants, you know, there's a 60-year-old man, let's say, and he's looking for a 45 or 50-year-old woman. Obviously, they're, you know, they talk about, well, I prefer younger, they keep, you know, their energy is like mine. There have been times where I do listen to my clients. I will show two, and I'll just use that example. I'll show two women. One is 55, one is 45. I give both, I tell them everything, show photos, don't give the age yet. Do you know how many times they end up picking the 55-year-old over the 45? So a lot of it, I think, is in people's mind. They know the age. I tell my clients all the time, I promise I am not going to lie to you. But if you give me a range, I will give you a woman or man in that range, but the age will come last because it's amazing how excited someone gets. And then they realize at the end, you know what, you're right. Like it doesn't matter how old they are. I'm super excited to meet this person. So age is a funny thing. I think it comes into play when you're younger, if you want to have a family, that I very much understand. But I think as we all get a little older, um, again, I respect what people want, but I also don't want them looking for a certain age for the reason that, as I said, I could fool them very quickly, you know? It's all about your lifestyle, your energy, what you're doing at that stage of your life that I think is important.

Tamara: 8:28

Yeah, and I know you talked about bodies earlier too, because some people, I think some men think like a certain weight is a certain thing, like a certain look if you're a certain weight. And they don't realize like how much more some people or less people can weigh than I don't like their ideal is a certain age or a certain weight. Right. And yeah, I read it. There was a thing about like a woman who was like, I don't know, she probably weighed like 150 or something. He's like, Why wouldn't date anyone over 125? And he was like, She was like uh I I weigh more than that. Like, what do you and he didn't even know that she he was like above her his ideal. Right.

Cheryl: 9:01

Well, you know what's funny also, I love the people that ask for, let's say, an extremely physically fit woman or man, right? But then they're not physically fit themselves. So I always say, you know, your expectations have to be realistic. If you're someone that goes to the gym five days a week, you eat very healthy, and you you really want someone to maintain that healthy lifestyle, I totally understand that. And I think everyone wants to be with someone who is physically fit. That's the way I like to say it. Now, do I have some people that will say I prefer thinner or maybe a little more voluptuous? Absolutely. Does anyone come to us and say, I want someone overweight? Of course not. Nobody comes to us and says that. But I think as a matchmaker, our job is really to bring out all the most important things about someone, really, their attributes, all the wonderful qualities. And sometimes, depending on the client, when they hear all that and they realize, like, let's all think about it. Wait, that can change, right? Something like religion cannot, age cannot, professions, depending on it, can change, location can change. But when you're talking about wait, how easy that can change, I try to tell my clients, try not to focus on that as the most important thing for that reason. So, and a lot of times they listen, they really do. We we form a really great relationship, and I think the most important thing for me is for them to trust me because I know that once we form that bond, the whole process is so smooth and it's really enjoyable for them, very enjoyable.

Tamara: 10:35

Yeah. Have you ever had tricky clients where they're like insistent? And then like I've seen a few matchmaking shows on you know on TV or like Netflix or whatever, where they're like the guy is just adamant that he has like the hottest woman ever. Absolutely.

Cheryl: 10:51

And they won't budge. Absolutely. I've had incidences where I have interviewed men. Now remember, just because I interview someone doesn't mean I'm going to sign them up. Okay. And I really mean that. I've turned people down based on what you're saying. So I had this actually politician. I got referred, he got referred to me, excuse me. And let's just say this he was about 73. And I interviewed him. We had a wonderful talk. It was for about an hour, hour and a half. It was great. He was very kind. So then when it came down to the last question I asked, so do you have an age preference? Now remember, he was 73. Okay. He told me somewhere in the 30s. 30s. So right there, I realized, wow, okay, this was a total waste of my time. I was very kind to him. And I said to him, I have to be honest with you, I am not judging you whatsoever. This is your life. You're entitled to a date, what you want. I will not be able to work with you. I have plenty of women in their 30s. I don't have one woman in their 30s who I would call for a 73-year-old man. So I asked him. I came out and asked. We had such a lovely talk. I'm like, what just out of curiosity? Because remember, he had kids older than that. What do you have in common with a 35, 38-year-old? And this was his answer. He's like, look, I know I'm not the best-looking man in the world, but I have money and I have a lot of it. And I'm okay helping a girl out financially because I think I will get her to fall in love with me. That was his answer. So it was an interesting answer, right? So I said to him and I said, that's not a problem. So he actually offered me double my price, okay? Double, just for me to work with him. And I said, listen, with all due respect, there will be plenty of matchmakers that will take you. Um, for some people, it's not a problem. And again, there's no judgment on this. I don't have that in my database. And I won't work with someone that is looking for someone 40 years younger. It's just not the way I work. And I, and again, he threw in, do you know how good it would look if you set me up? But you know what? You know what was worth it all for walking away? For me being able to tell that story so people understand who I am and the way I work. So, but yeah, so you know, I don't take people like that.

Tamara: 13:22

Yeah, yeah, it makes sense. Yeah, like you said, I mean, it would be like when I got set up and I was like, I really don't like older, and they're like, oh, just try it. And it's like, all right, but yeah, that's much different. I mean, he wasn't that much older, but yeah.

Cheryl: 13:34

Well, and you prefer younger. So remember, if you were a member in the database, matchmakers aren't catering to the members. We cater and work for the client. So what we do is really trying to make the client happy. Now, clearly, you want the member and the client to obviously see eye to eye. Um, for me personally, if I knew that about you, I wouldn't be pushing you to go out because I would know right off the bat, like, okay, this is someone who prefers younger, you know. But again, if you were the client, you probably wouldn't have been introduced to a man that's older.

Tamara: 14:08

Yeah.

Cheryl: 14:08

That's usually the difference.

Tamara: 14:10

Yeah, for sure.

Cheryl: 14:11

Yeah.

Tamara: 14:11

Yeah. And then um do you give, do you have advice in general for like I know more people are getting sick of the apps and they're trying to do it in real life? Is there um obviously you do introductions, so that was probably something you would um recommend, but any other tips for how to how to introduce someone if if even if like a relative or a friend or something?

Cheryl: 14:34

Absolutely. You know what I found that you know I've done, I actually wrote for the Sun Sentinel here in Florida and I wrote an advice column. So it wasn't pitching my company or anything like that. And one of the things were like if I was single, how do I meet people if I don't want to go on the app or go to a matchmaker? Let's say someone's not ready to do either. You know, I always say this, and I used to say this to my kids when they were looking for jobs. If you sit home, no job is coming knocking on the door saying, I heard that you're looking for a job, right? It's the same thing with being single. No random person is just gonna come knocking on your door because they heard you're single. So does there have to be effort? Absolutely. But my suggestion always is the more you get out, the more opportunity you have to meet someone. But it doesn't mean you have to go to a bar, a plug. Um, but what um I always suggest is doing something that you enjoy. For an example, if you enjoy working out, steadily going to the gym is a great way to meet someone because right off the bat, you have working out in common. Or if it's playing golf or pickleball, anything like that, um, again, you already have something in common, the pickleball, the golf, tennis, right? Anything. Um, going to a bookstore, what's interesting about that is I know a lot of people have met that way. Going to a bookstore and maybe sitting at a table, having a cup of coffee, doing something, a lot of single people tend to find that very relaxing. Um, I always say you could be at the supermarket, you could be in Starbucks and meet your future person. Usually the best thing is smile. The more you smile, the more inviting you feel. And eye contact, like when you're walking in um to even your supermarket, if you're looking at your phone, you're constantly looking around. But the more eye contact you give people, I always noticed single people tend to do that a lot. Usually people that are married, whatever. If I had to go to Publix, I'm going, I'm getting what I need, and I'm leaving. So I think the more you get out, um, the more things that you try, um, the more events you go to. Sometimes there's networking events. Just because you know, you don't have to be going to a single event to find someone, maybe there's a wonderful networking event or an art class you could go to. And I think there's so many different things that people can do. But when you're sitting at home, just think about it logically. Who are you meeting? You're not, you're not.

Tamara: 16:55

Yeah, yeah. Yeah, it seems like a lot of people are trying that tactic too. Be like, they'll just eventually it'll happen. Yeah.

Cheryl: 17:03

Well, and some people do believe in that. Some people believe, look, when it's meant to happen. You know, I've had people say that to me, and it's funny, I do a lot of my recruiting on my own, right? And I do a lot through social media, networking people. So I have reached out to people, and it's so cute. I've had so many women say to me, Oh my God, I was just talking to my mother. I said, that's it. I'm done with the apps. I think I just have to wait for a sign, and all of a sudden I got your text from this matchmaker. But it's true, that is a sign, you know. I feel like everyone comes in your life. This is my little motto for a reason, a season, or a lifetime. And sometimes it's a girlfriend, sometimes it's a relationship. But if you think back, usually it is some sort of reason or a season, maybe it's summer, maybe it's the holidays, maybe it's something like that, or hopefully again, you know, for a lifetime.

Tamara: 17:54

Yeah, yeah, definitely.

Cheryl: 17:55

Well, we and we were talking about the apps too earlier, you and I. And, you know, the apps, listen, it's convenient. It's very convenient. But I think what I hear from a lot of people, Tamari, is the fact that, you know, it has gotten so watered down. Um, you don't know if you're talking to a man, a woman, are they trying to scam you? Are they trying to, you know, sell you something? And the latest one I heard, I just had a girlfriend ask me my opinion about uh this guy. And he was super good looking. And I was so excited for her. And I was going over, like, look, this is where he went to school. But she's like, Can you help me find him? And I'm trying to Google and Google the town. Long story short, I get a text from her an hour and a half later. He's AI, forget it. So now there's people going on there and they're AI people. So I think the apps are getting extremely frustrating for people. Um, I think it's becoming more than a full-time job. And so that's why I think a lot of people are going away with the apps. Matchmaking is getting so incredibly popular. I mean, you hear this more and more. And I think in real life events, which a lot of people seem to enjoy very much.

Tamara: 19:00

Yeah. Can people reach out to you or matchmakers in general to get on to be in the database? Or is that something you kind of search for yourself? I know you said you recruit.

Cheryl: 19:09

So yeah, no, I well, we market, we recruit, but actually, and again, it's probably because I've been doing this for quite a while. I probably get two to four women or a man who reach out to me based on a referral referral, excuse me, pretty much daily. Daily, like at least one person every single day for quite a while, which is wonderful because now that we're not just in Florida, we are expanding outside of Florida. So, and we have a lot of connections outside of Florida. Um, we work with some other matchmakers in certain areas where matchmakers will call me. Um, something else that's more new for us. Um, clearly, we have a straight database of men and women, and we have a very large database of gay men now. Um, in the last year and a half, that has grown tremendously. I would say I started about four years ago, and now we just grew an incredible huge database of gay men. So a lot of matchmakers that know that will refer us, you know, to men that may be approaching men, because that's obviously a whole nother category, and we work with them. Um, but overall, our entire niche for Everyone are professionals. That's been my niche since I started. And that's something that we really stand true to that everyone in our database is a professional or retired one and basically can financially take care of themselves.

Tamara: 20:30

Okay. Yeah. Do you want to share how people can is it just matchmaking.com or is there more to Yeah?

Cheryl: 20:36

So it's www.matchmaking.com. Um, for women, they can fill it out. Women are always free. So they are free in our database, and the men are our clients. So either if you're a man or a woman, you could fill it out right there. And as soon as we get your response and your profile, the appropriate person, whether a matchmaker, recruiter, will reach out to you.

Tamara: 20:58

Okay. All right.

Cheryl: 21:00

Anything else to um share about your services that I forgot to ask or no, well, I mean, everything pretty much like we said, I I love what I do. I have a phenomenal team of everyone who just, you know, we're not working because it's a job. We are really working because we are all passionate about putting people together. And I always say the more people I can help from any age, and actually, I just had an engagement over the weekend. My 83-year-old client who came to me a year and a half ago, um, was married for 63 years to the same woman. He was widowed, came to me, I set him up, and literally they just got engaged this past weekend, getting married in a few weeks. So we take any age, as young as in the 20s, all the way through the 80s. So if anyone is single or knows of anyone single, to have them reach out to us because really, I really believe there's a lid for every pot. There really is.

Tamara: 21:54

Yeah, yeah, definitely. Yeah, that's awesome. And yeah, I was just I was gonna ask how many, like percentage-wise, do you if you have that percentage, or would you say a lot of them meet their person or at least get in relationships?

Cheryl: 22:09

Oh yeah, we have an over 90% success rate for sure. We have over 90%. I would say there's a few percent that let's say have a wonderful process, um enjoy it, uh, maybe date it for a few months, and then they end up rejoining us. And then there's always that three, four, five percent where maybe they tried it out, but like they realize they have to do some work on themselves. But we have a pretty high percent, yeah, a pretty high success rate for sure.

Tamara: 22:33

Okay. Well, are there any like closing thoughts, final comments that you want to just leave?

Cheryl: 22:39

Um, as I said, just you know what? I as I said, if you're looking for someone, there is always someone there out there looking for you too. Um, you know, matchmaking is really the new way to meet someone. And if you're interested, to definitely go to our site. Um, we would love to speak to you. And we really have such wonderful men and women in our database that are waiting for their special someone. So to definitely reach out.

Tamara: 23:05

All right, awesome. Well, thank you very much.

Cheryl: 23:07

You're welcome. Thank you for having me tomorrow.

Tamara: 23:09

And if you love this episode, be sure to tell your friends about it and rate it as well, and follow the show, of course. All right. Well, thank you again, Cheryl. Thank you, and definitely check out matchmaking.com.

Outro: 23:19

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