Inside the World of LGBTQ Matchmaking | Interview with a Gay Matchmaker

Hi, this is Suzanne Noble, and you're listening to Sex Advice for Seniors. Have you ever thought what it would be like to hire a matchmaker, especially if you're a gay person? Well, Tammy Shackley is a matchmaker who, although she's not gay herself, specializes in matchmaking people who are LGBTQ. And I think that in itself is fascinating. And not just that. She's just told me that she lives in Panama and of all the guests I've had, that's probably one of the most exotic locations anyone has ever been resident or situated in. So I'd really like to welcome you, Tammy, to Sex Advice for Seniors.

Thank you for having me. I feel honored and I've enjoyed listening. There's so many licensed certified professionals like you that offer so much advice. It's an honor to talk to you.

Oh, thank you. And I'm not certified in anything, just so you know. I'm just, I'm just a very curious person who has spent more than my 10,000 hours learning and delving into and experiencing the world of sex and dating and relationships as an older person. And I think that gives me some qualifications for knowing what I'm talking about. But mainly I talk to people like you to find out what's actually going on. Because I don't have a clue, although I've always thought, what would it be like to hire a matchmaker? So I'm really curious just to start with, how the hell did you decide that you were going to become a matchmaker for gay people when that's not your sexual orientation?

Right. The number one question asked for the last 14 years. I went through a divorce, no children, moved to Austin, Texas, in the US. And started my life over. And now I know not to say start over, but to start the next chapter. And I was a very private person. I did not want to do online, which was popular at the time. Instead, after 2 years of healing and rebuilding, I thought, there's gotta be people for this. And so I called a matchmaker, hired them. It's how I met my husband.

Wow. Amazing.

Yeah. And so a couple, and we dated for a year and a half. We're engaged for another year. And then a couple of years later, a friend said, who was gay, "I'm a very private person too. If you could create a gay and lesbian matchmaking company, I would be your first client." And I thought, well, there's, that's already been thought of. That's already out there. I told him, I'm going to go home from lunch and I'm going to research and I'm going to find you a matchmaker. And I couldn't. So for 24 hours, I pretended to be a 40-year-old gay man physician who was going to go online and find a dignified way to meet other professionals like me. And what I found was not dignified at all. And so I said to my husband, I think I'm supposed to do this. I'm at least, my background is news. Politics and philanthropy. So I knew how to tackle a community issue with a feasibility study and a series of focus group interviews. That's what we did at the Community Foundation. And in that process, I realized I did not know matchmakers did not serve the gay community. And I couldn't understand why, that they weren't asking the right questions or doing the right research. Why is this an underserved population in a growing trend of offline personal matchmakers? That's how it began.

Yeah. It's so interesting because one of my closest friends is an older gay man who has been single for most of his life, I have to say, and he lives in New York City and it's a really, really hard place to date. It's really hard. And also what I've heard from him and other older gay men who would like age-appropriate partners is that it's almost impossible. Not, not just because, because the older gay men are out there is what he tells me. But often the men that they want to go out with are much younger and much younger men often want their sugar daddy or whatever. Older gay men want their Twinkies. And so, so if you're an age-appropriate guy who wants another, you know, an older guy wants another guy of the similar age, it's really, really difficult. Really difficult.

And that's where I, I never did online dating. I never, you know, the apps have become popular since I was even launching the company 13 years ago, but those are used for other purposes. Yeah, yeah, for sure. Yeah, they were started as introduction services, um, but it's turned into something else. And so those like your friend who just want to meet someone equitable in age, stability, financial success or responsibility. Those are hard to find. They're all out there, but how do you find each other? And that's what matchmakers do is we introduce you to someone that more than likely you would have never met on your own.

And how do you, um, of course, the next question that seems really obvious is how do you go about, because we know that the landscape of online dating is especially within gay male communities. I don't know if it's the same for women. I know I have a female friend who's, who's poly, and she's met women that she's had more casual but still ongoing relationships with. So maybe with women it's maybe not the same. I don't know. But how do you go about finding these people?

Right.

And is it like nationwide or do you see It is nationwide.

I've interviewed gay singles in 16 countries, but I only match when they're in the United States. Oh, right. I do match coast to coast in the United States, but I'll talk to anyone and help them if I can refer them to a matchmaker in Canada, for example, or in the UK. I have those referral sources and they call me the Fairy Gay Mother because I'm a little bit older in the niche and I'm really working with all singles to get them to the right place. But you have to start somewhere. And what I started with that client, the first client was really scouting the 50 most eligible bachelors in Austin, Texas. So once I knew 50, I was prepared to interview him. So that's where my style is different. As a former reporter, I like to interview a person for an hour, hour and a half, and really get to know their human interest story. And sometimes people interview with me that don't end up. Retaining us, and that's okay, but they're in my database now and maybe they're an eligible and compatible match for one of my clients. So I talk to everyone and then we see who is best suited to work with me and that I'm best suited to work for them is how I look at it.

And do you see that it's that when people come to you who are over 50, the requirement is different? Than people who come to you when they're younger?

It's a good question. And I don't know that there's an answer for that. Everyone is so unique in what they're seeking in compatibility and who they think is compatible for them. So if, you know, someone much older requests someone much, much younger, I, my joke is there's an app for that. That's not really what we do. That we really match those that want equitable in age, in lifestyle, in travel, in health, fitness, wellness. You know, we have some large clients that are, that are bigger, bigger guys, right? And they hope to meet the same. So it's not that they have to fit into this box. We meet them and we get to know who they are and what they're seeking. And we want them to stay just as they are. You know, that we would, we don't want them to change to meet the right person. We want to find the right person to meet them.

And would you say that the proportion of men to women that seek your services is predominantly men?

I was shocked by that. So when I launched the company, first introducing men while doing the research with the women, and I have had LGBTQ clients over the years, but mostly we work with lesbian women and gay men, and organically it's become 50/50.

Wow.

It's a great thing. Yeah, I was surprised by that as well, because the focus group research with the women that were so honest with me during the process, they said lesbian women aren't going to pay for this. And I said, well, you know, I've had my waiting list is long enough and it's priced affordably to get started. So let's, let's see. And then it immediately became 50% of my clientele.

Wow. That's amazing. How many, I'm curious, is the original guy who led you to start the business, Is he somebody that you found a match for?

He is matched in a significant long-term relationship with one of the bachelors in my database. Amazing. They have an interesting story. And then I have so many stories of men and women that have come to me of all ages. I like— I'm 58 and I like working with singles who are 50 and better because they're just They've led oftentimes such a rich life, education, travel. They're worldly. They're, oh gosh, so wise and vibrant and still just have this zest and sometimes a new zest for this next chapter of their life. So it's inspiring to me.

So you just teased me with that little, that little, like, what's the story with the first one?

Oh, good. Oh, so they had been friends for a long time. And I knew that. So they were both in my database. I'm matching the one that was my client, but I knew that they had had long-term friendship. And when they both celebrated each other's 50th birthday on their group friend trip. They both came back from those two trips and met to reveal to the other that for the first time they have romantic feelings for each other.

Oh, really?

They were both waiting, like, before we have lunch, I have something I have to tell you. And the other one said, no, no, no, before we have lunch, I have to go first. I have something I have to tell you. And they both revealed that their romantic interest in each other had grown. Oh, that's incredible.

What a lovely, lovely story.

I love it for singles because so many times, you know what you know, you want what you want, and you're used to getting it at this age. And, oh, Tammy, romantic love can't grow. And I said, you'll see, you'll see. And it's one of the reasons we manage the first two dates when we do an introduction, because there's people with a mindset that I'll know in the first 3 minutes whether he's my guy or she's my gal. I think it doesn't always happen like that as we're older, maybe in our 20s, we felt that, but when we're older, wiser, and more experiences, give it a chance to grow a little bit. And sometimes by the end of the second date feedback, they'll say, at first I didn't get why you introduced us. But after, you know, 5 hours together now and walking and talking and touring a sculpture garden, I see why you introduced us.

Yeah. And I think that's one of the problems with the apps, frankly, is, is that we are too quick to judge by somebody's appearance. And so we swipe by people that potentially could be good matches. And then when we do meet them, we expect expect this kind of instant spark. And I think as we age, that spark takes longer to manifest itself. It's not, it's not a spark so much as a little ember burning away. And I often say to people, especially women that I know, look, you know, you don't really know this person. It's going to take ages. Like, 2 dates is nothing, you know. Talk about a year down the line or, or whatever, but you can't judge somebody just after the first date.

Absolutely.

You, you know, obviously there are some things about a person that you might decide are deal breakers. You know, people's political affiliations might be something that really bothers you and other people it doesn't bother them as much, you know, but it's just give somebody a chance.

Absolutely. You know, the anthropologists that I follow say it takes 4 good dates when you meet someone new to even see if there's potential for your future. And then a lot subscribe to, it takes four seasons. It takes a full year to truly know someone. And so to me, I think almost everyone deserves a second date because not everyone's extrovert. You don't know what they're going through. You don't know what day, kind of day they've had. So that first introduction's nerve-wracking for everyone. The second date, you know who you're meeting, you know, even your resting heart rate's a little more chill and you can be more yourself ideally. So I think everyone's, you know, worthy of a second date. Even if you're finding out their friend circles and who they know, if you let the universe be at work to guide you to meet the right person, I think there's a lot of power in that.

No, I completely agree with you. And as you said, it's It's also about the first date. People can be nervous. They might've had a really rough day. You don't know what's going on in their lives. And, and we all then expect everybody to turn up being perfect. And, and then of course it takes months for our perfect person, our perfect shell to start to disintegrate so that we can actually reveal that we're not so perfect underneath.

Right.

You know, I, I, I know myself that especially if you don't live close to the person that you're dating, so you don't see them frequently because frequency does tend to escalate how quickly you get to know them. But if they're living far away, it can take months to actually work out whether this person is even remotely compatible with you.

Absolutely. You know, our other location, we moved into a 55 and better community and it's been so interesting watching The singles in the community talk about online dating and, oh, you know, Tammy, would you help me with my profile or photos or whatever? And I'm glad I, I don't match hetero singles, but I'll advise them all day long. And when I see their pattern, like sit in front of me and swipe, you know, yeah, I will say every woman swiped on him. You're, you now everyone's after him, but why did you pass up that kind of nerdy, kind of tall, little bit geeky guy? I'd go back and swipe on him because he's the one that's probably rock solid, loyal, just a good guy, kind of that invisible nice guy that everyone's passing over and he might be your guy.

Yeah, it's such a good point. So taking that, um, into the world of LGBTQ people, what What emotional hurdles do you see them having to face and how do you support them through that process? Because clearly they've, you know, they've had several relationships. They might have been widowed. They might be, you know, they've, you know, they've, they've had a time of it. It's not like they've just started. What, how do you support them through that? And what do you see?

Thank you for asking, because the number one thing that tends to come up in the interviews is Tammy, I've done the work, you know, whether they're widowed or a traumatic divorce, or they had a domestic partnership, but it was such a situation before marriage equality passed in the US. I mean, there's just, there's a journey there. And when they say, I've done the work, I hope to meet someone who's done the same. I think that's important. I think it's very self-aware of the journey that they've been through and they're not looking to heal someone or to be healed, they want to meet someone who has equitable emotional maturity, stability, and availability.

Yeah, not easy.

I think we're all a work in progress. We're all a work in progress. But to admit that it hasn't been easy in the LGBTQ community, but I've done the work or I have the support system, or maybe my family doesn't support me, That's why I have chosen family over the holidays, you know, so I'm listening to the cues of their health and wellness too, to make them relationship ready or to put them in a position of being ready to meet a real potential partner with sustainability. So it's not that anyone comes all set and ready, but they're very self-aware and honest about what they've been through in where they are today.

Yeah. And do you, how do you help them to distinguish between what are just what you would see as healthy standards and being too rigid in their outlook to be able to find someone?

Well, even with age that you brought up earlier, when we get to that part of the interview, I word the question this way. What age range do you think is compatible with you today? And so they better be honest with themselves, right? But then we also talk about what do you think is compatible with you? Oh, your lifestyle is— I'm making this up— you watch football, sports every weekend, all weekend long. Be honest about that. There are people that will fit into and be compatible with that lifestyle. And there are people that won't. When someone tells me, "Oh, Tammy, I'm a texter. I love to text my partner 25 times a day," then we talk about attachment styles. I'll give them some homework assignments about love languages, attachment styles, and really being aware of what type of single you're coming to the table as, and that limits who I might introduce you to.

Yeah. And I was going to say, so it sounds like you're kind of part matchmaker, part therapist, part, part coach.

I encourage therapy. I feel like, because I am a certified matchmaker, but not a licensed therapist, but I've been to therapy, right? So how I look at it is, um, I'm the trusted aunt that I love you no matter what, but I'm going to give some tough talk and you may not like what I have to say., but I'm going to coach you on this one more time. Stop oversharing on a first date. If you don't, I'm not going to set you up again. Like, you know, your aunt who loves you will also shoot straight with you.

And I was going to say, speaking of that, so you're, you know, you're sending people on these first dates. What does a, what does a first date look like for two people over 50 LGBTQ who are serious about a long-term partner? Not just looking for a hookup.

Right. It's really, it should be lighthearted. It should not be an inquisition. It should not feel like an audition for marriage. It should be lighthearted. I'm coming to this drink and appetizer, meeting you. Gosh, I had to let my dog out before I came. Do you have it? Do you have pets? Do you like dogs? Uh, mine's a rescue. I, I even volunteer, you know, with pet rescue or whatever, it should be light-gridded and little peppering of who you are and what your day was like and what your week is like and what this year is like for you, but not diving deep, not diving deep. Yeah.

No. So you say the diving deep for the second date.

If you wait to a second date. Well, I'm a visual learner, so I believe in the 4-date rule, right? So on the first date, really lighthearted. Talk about live music, plans for travel that you have. Second date, go a little deeper, just slightly. If you get to the fourth date, let's talk about past relationships and how you grew from that and what you learned from that in a healthy way. But don't bring it to the first and second date.

Yeah. Yeah. I always say it's always a red flag for me if a man turns up on a date and starts telling me about his crazy ex.

Yes.

Right.

Because then he's going to talk about you. Right. So yeah, what you've done, you will repeat. And so I, I, one of my matches through my own matchmaker, he had not been divorced long enough. I think a good 2 years, you know, is a good timeline I subscribe to, but I heard all about her, heard all about her. And I thought, well, bless her heart, you know. Because I didn't really learn anything about him.

No, but also for me, when somebody starts talking about the crazy ex and not that there aren't crazy exes, because, you know, there are crazy exes. So sometimes, but for me, it's like, well, what does that, you know, what did you learn from that?

Yeah.

What, what, how did you grow from that experience? Like, what are you not going to do again?

Right. I always appreciated when someone would say something kind. About. So I used to say, you know, he's a smart guy and he's a good guy. He's just not my guy. Yeah. You know, that this time I want a guy that loves me back, you know, and I would say that. And because it was positive that he wasn't a bad person, we weren't the right combination. That's all.

For sure. I introduced my ex-husband to his current wife. They just celebrated their 15th wedding anniversary. I'm extremely happy about that. We were only together for 10 years. And he's managed to, well, I think, you know, they're in for the long haul, which is great, which is great really. So how, what was it I was going to ask? So many people haven't dated in decades and so they're going out there and what are the kind of simple concrete things that they can do this month to just become more approachable and date ready?

I love that question. Refresh, refresh, because At 50, when you're wearing the clothes you bought early 40s, and at 60, I mean, every 5 years you should refresh and start now with the first refresh. And I tell the women, get new foundations. What you're wearing underneath makes a difference on how you feel and how you present. You know, try a new hobby once, just once. Join a new Facebook page of like-minded people about pets or paddleboarding or cooking, you know, a refresh to get you out of what you always do because you've always done will help rejuvenate your lifestyle. You don't have to change everything, but throw— just like we throw out old clothes, throw out some old habits. Go to a new coffee shop, go to a new pub one time that you've never gone to, because you can start to be your own matchmaker by putting yourself in situations with new refreshed people as well. I love a new grand opening of any type of eatery, coffee shop, or gallery, or it can be anything. It can be, you know, a pop-up cupcake bar. I'm not advising you to eat cupcakes, but go check it out because on a first date you can go, this is crazy. I went to their grand opening or checked out that place around the corner when they opened. Let's go split one because I can't handle the guilt of a full cupcake, but let's go try it together. You know, it's something fresh in your neighborhood, in your community, in yourself, on you, a fresh haircut. Ask your friends to style you the perfect first date outfit because they're dying to tell you, but you never ask.

I think it's a really good idea because it's not just about freshening up the way you look in your appearance, but also just giving you a change of outlook, isn't it? It's about saying, I can, you know, I just look through my TikTok videos to see the many, many hairstyles that I've had over the years. And then my friends and I decide which one is actually the best for the next, the next quarter. And without naming names, can you tell the story of an over-50 client who thought it might never happen for them and what changed?

I'm going to tell you two real quick. One or two, uh, one story, two men, one 59, one 66. One had come out of a 25-year relationship, the other out of a 31-year relationship. So here we are, both men said, who comes out of a relationship, you know, a gay relationship this long? And where do I begin? Like, is there anybody else out there like me? These two men could empathize with each other because after such a long gay relationship, it became a sexless, a loveless relationship with four really nice men. And now they're married, you know, and the daughters, one adopted daughter's graduated college. I mean, it's such a celebration, but one of the best calls, which you can call us, you can email us, go through the website. It doesn't matter. We're always available. But a woman called and she said, I'm 66 and I'm so excited, ready to get started with you. And I said, Well, slow down, what's your name? Like, this is a process. And I said, no one has really called me with such enthusiasm, ready to hire me. And she said, these were her words, I just got off the phone with mother and daddy in their late 90s who were still independent and in love and taking care of each other. And I realized, even though I'm widowed for 2 years and my grown children have helped me grieve and recharge and get, you know, more fit and healthy. I realized with this phone call to my parents, I have a 30-year relationship in front of me. We got to get started, Tammy. I was so inspired. I think I only met— I only matched her twice. She got into a relationship and I never matched her again.

Amazing.

She had done the work, you know, she was self-aware. And she had such a zest for life in her next chapter. She couldn't wait to read it. She couldn't wait to create it.

That's such a great and inspiring story. And it also just reminds me that when you approach dating with positivity and excitement and hope and happiness and everything, it's just so much more attractive to everyone around you than going into it with this like, oh, I'm never gonna meet anybody. It's all gonna be shit. Who's out there for me? Nobody's out there for me. I'm just a loser. You know, that kind of attitude is just always going to be compelling.

It's magnetic. When you, you have love for yourself, not every day the max, you know, let's be real. Being real is important, but When you have love for yourself and love for the life that you've worked so hard, or, you know, have tried or retried to design for yourself, that's magnetic. People want to be with someone who's kind, who's happy with what they do have, not what they don't have. That is what people are attracted to.

So finally, I have to ask you, someone's 50-ish, they're curious, but they're hesitant to reach out to you. What can they realistically expect in the first 30 days of working with you?

A phone call. We really do just start by talking on the phone. And ideally it would lead to a complimentary Zoom interview, but if they're not ready for it yet, that's fine too. Let's keep in touch. If they want some homework assignments, sometimes they'll ask me for those. We share the, you know, here's what you can start to do to prepare. If they want to set a goal, like let's talk after the first of the year, or let— I have multiple people that have said, I kind of want to get in better shape after this health scare. So let's talk after my doctor has said that, and he thinks I'm ready, or she thinks I'm ready, or my therapist, right? So it really, it's, it's based on where you are. I meet you where you are. And we start the process there. If you retain us, Then you've got your first introduction and you're starting to meet people usually once a month. You meet someone new and we're managing the, the introduction. We're picking the place, we make the reservation, we do a live feedback call. It's confidential. So we're helping you get to know all of these matches until one feels like the right one for you.

That sounds a lot of fun. And I wish it wasn't just gay people that you worked with.

There are tons of hetero matchmakers that I refer anyone to. Anyone is welcome to call us. And I had a call this last week from an outstanding couple who— a gay couple who's looking for a third. And I resourced that for them to get them to the right introduction service for that. Wow.

I didn't even know that there was such a thing. That's really fascinating. And how much can somebody expect to pay for your wonderfulness?

In the thousands, but not in the tens of thousands is how I look at it. Is that, and there are matchmakers out there, very high-end celebrity level, you know, the penthouse in New York City, right? Those are out there too. I think you have to find the right matchmaker for you because we are in a relationship that just like your aunt, right? You have aunts that aren't your favorite and aunts that are. And so I hope to be your favorite aunt. Yeah.

And I, and, and I think that, you know, what I'm hearing you say as well, and what I'm feeling from speaking to you is that you're building the relationship with your client while you're trying to find your client a partner. So if you don't have a great relationship with your client, then there's no relationship they're going to find with their partners. So somebody really has to like you and you have to like them. As much as they are eventually gonna like somebody else. Because if you don't like your matchmaker, then it's likely that they're not gonna find you a match. And I suspect that finding a matchmaker that actually is relatable and you think this person gets me, they understand me, they know what I want, is super important when you're spending this kind of money. Because— Absolutely. I have girlfriends who, and in fact I had a former partner, I ended up meeting him on Tinder. And he had gone to a matchmaker and it was a disaster, an absolute disaster. And every match that he was like, I don't even understand how this person has put me together with this person. We are as incompatible as it's possible to be. And he felt it was sort of out of desperation that he'd been matched with them. And he felt really Well, he just felt depressed about the whole experience. So I think in order for it to be a really positive experience, which if you're going to meet somebody, it has to be positive, you have to find a matchmaker that you love.

Absolutely. Because my filter has become, would I have you at my holiday table while I'm interviewing my singles? Would I have you at my holiday table? That's what I want to feel about you. And would I set you up with one of my siblings? If they were gay or lesbian, because then you would be at my holiday table, right? So I look at it also in the industry of certified matchmakers, those that have a servant's heart versus those that are just trying to make commission by having a client. So I think to be selective are the matchmakers that do the best job. I decline some clients that, some singles that I'm not the right matchmaker for you, but let's try to find you the right one. And, and I'm, I'm passionate about that because I found the right matchmaker for me and it worked. And so now I'm passionate about helping folks find the one that feels right, that's going to serve you with these introductions, not just get you on a date. You can get a date on your own. Matchmaking should feel different.

I agree, and it's been absolutely lovely to talk to you. Have a wonderful day in Panama. Have a lovely time over the holidays. And good luck. And for anybody who wants to get in touch, I'll be posting all the information about Tammy. If you are LGBTQ or you know somebody that is that might want to be matched up, then I think she sounds fabulous.

And thank you. Keep up the good work. I love everything you do as well.