This story is brought to you by our partners at Matchmaking.com
I couldn’t help but wonder… In a world of dating apps, algorithmic soulmates, and commitment-phobes disguised as brunch dates, was there still room for offline, old-fashioned matchmaking?
Enter Cheryl Maida, a passionate, professional matchmaker in the business of love longer than most of us have kept a relationship alive past cuffing season. For 16 years, Maida has built relationships from the ground up — no swipes, no catfishing, just deep conversations, highly customized matches, and an uncanny ability to see past the curated selfies and into the heart of what someone really wants.
From her early days interviewing strangers in Florida Starbucks to now directing a national team at Matchmaking.com, Maida’s love story with love itself is as real and rich as the matches she creates.
I caught up with her to talk about gay dating pitfalls, first date faux pas, and why being “too picky” might be the one thing keeping Mr. Right (or Mr. Big) from ever showing up.
Cheryl Maida, Matchmaking.com's Director of MatchmakingPhoto Courtesy of Matchmaking.com
OUT: Let’s start at the beginning. How did you go from recruiting for jobs to recruiting for love?
Chery Maida: It started organically. I was a corporate recruiter right out of college. I loved helping people find jobs — especially those who were stressed, burnt out, or in a rut. Then after raising my three boys, I needed something more, and my dad gave me the idea: “Why not become a matchmaker?” I started on my own 16 years ago — literally with business cards. It was just me. A boutique business. I have gone to every Starbucks from Miami all the way to Jupiter, and I would meet people there, interview them, and they would come into my database.
That’s an incredible origin story — and now you’re leading Matchmaking.com. What does your role look like today?
I do thorough interviews with each client. The most important thing is to really learn who your client is, what they’re looking for, so we can make the appropriate matches.
With over 16 years in the business, how has matchmaking evolved, especially for gay clients?
When I started, the apps were just coming out. People were embarrassed to say they were on one. Now? Apps like Grindr are full of scammers or people looking for one-night stands. A lot of my gay clients are looking for longevity. They want something serious — and they can’t find that on an app.
There’s a myth that you’ll just magically meet someone. What do you think about that?
No single person is just going to come knocking on your door like, “Hey, I heard you’re single!” It’s equivalent to looking for a job. You don’t sit at home and expect one to land on your doorstep. You get your resume out there. You start talking to people. That’s what it’s like to be single. You have to take steps.
What challenges do you see gay men face in dating today?
The biggest challenge seems to be finding men who are serious about finding something real. That’s what I think. Where do you find them? The answer is here — Matchmaking.com. We recruit for every individual. No two clients want the same exact man.
What makes a gay man ready for matchmaking and what’s the process like?
When someone fills out a profile, takes my call, sits down for the interview — they’re ready. If someone’s just divorced or widowed, maybe they need more time. I want clients to go on that first date with a clear head and a full heart.
Then, when we sign them up, it’s game on. We do a 45-minute interview. I ask very intimate questions — age range, religion, political views, hobbies, sexual preferences. And yes, I ask if they’re a top, bottom, or vers, because chemistry matters and I want to save time. Then they get a professional photo shoot, and we begin recruiting. Within a week or two, I’m already presenting matches.
How do you help your clients manage expectations?
I always say, if you wait to check everything off your list, you’ll be single forever. It’s okay to have standards — I’m all about that — but be realistic. You may think you want someone who is 6’5’’ with six-pack abs who makes X amount of money, but do you need that? Once people open up, that’s when the doors start opening.
Favorite success story with a gay client?
I had a client who was a doctor — very old-school and didn’t sign up at first. But we stayed in touch. Eventually, he signed up, but was very selective. I said, “Just trust me. We’ll learn from the first match.” That first date? One and done. They hit it off, and they’re still together. If he didn’t trust me, I’d still be sending him people.
Any first date advice for our readers?
Don’t be late. If you’re meeting at 7, be there at 6:50. Put your phone away. Make eye contact. Be a good listener. Dress for the date the way you want someone to dress for you. And be a gentleman. Even if it’s not romantic, I’ve had clients who became lifelong friends, business partners, travel companions. You can always get something out of a date.
Final words for our single gay readers?
There are so many more avenues than just the bars or the apps. Go to concerts or events. Get involved with the communities that align with your interests. And if you’re really serious — apply to work with Matchmaker Cheryl at www.matchmaking.com/apply-now. You'll be opened up to more than you think is out there. And it’s so promising.
This interview has been edited and condensed for clarity and length.
