51. Set Jetting with Tammy Shaklee, the Gay & Lesbian Matchmaker

Join me in this episode as I chat with Tammy Shaklee, the innovative force behind H4M Matchmaking and former President and CEO of the Make-A-Wish Foundation of Central & South Texas. Tune in for a sneak peek into our exciting Sex in the City cruise plans and themed nights, where Tammy's wingwoman skills and candid conversations promise to create an unforgettable escapade on the high seas.

Sex and the City Fan Cruise
@jetsettingwithmichele
Episode 38 with Molly Rogers
Vanity Fair podcast, "Still Watching"
Michele's Jet-Setters on Facebook
H4M Matchmaking
H4M on Instagram
H4M on Facebook

This episode was produced by The Podcast Teacher.

Transcript

Michele:

Welcome aboard Jet Setting With Me. I'm Michele Schwartz of Makin' Memories Travel, your luxury lovin', star-chasin', extra AF host. Grab your boarding pass and your best carry-on bag, and join me as we explore luxury travel for adults, the newest travel trend: set jetting, hacks to elevate your travel game, and places you can join me on my own wanderlust adventures. Fasten your seat belt, friends, as we jet set into a panorama of breathtaking sights and exclusive journeys like never before.

Michele:

Hello, my friends. Today, I have, like, one of my most favorite people in the entire world. I worked for her. I work with her. She is Tammy Shaklee of H4M Matchmaking. And I may have known her like pretty much half my life at this point. And she is such a bundle of energy. And without further ado, Tammy, please introduce yourself as well as h for m matchmaking to all of my fellow jetsetters out there.

Tammy Shaklee:

My dear sweet, sweet Michele, thank you for having me. Tammy Shaklee, the gay and lesbian matchmaker. You and I know each other through nonprofit work. My background is news, politics, philanthropy. I met my husband because I hired a matchmaker. Years later, I was trying to refer a gay friend, could not find him a matchmaker. It led to research, design, and I launched a gay and lesbian matchmaking company almost a dozen years ago. Prior to that, I ran the Make A Wish Foundation.

Tammy Shaklee:

Now I'm granting wishes by introducing singles to each other.

Michele:

Oh my god. I love that little tagline. That's awesome. Yes. And so, of course, we can both see our career trajectories from when we worked at Make A Wish because I did a lot of Disney wishes, and then I started the travel agency based on granting Disney memories. And then you just said the same thing. You're granting wishes by introducing people who love one another. But we have still managed to become, I think, even closer friends now that I don't report to you.

Tammy Shaklee:

Well, when we share a room at a resort

Michele:

Wait. Wait. Wait. Time out. It wasn't a resort. We were camping.

Tammy Shaklee:

We're gonna be at a better resort next year, thanks to you.

Michele:

Yes. We are.

Tammy Shaklee:

But the fact that you handled all that travel when we got to room together with all the matchmakers, that was great. And so I already know the quality and the curating that you do and your standards and the caliber of what you expect in service to where this was a no brainer this upcoming trip?

Michele:

Yes. Tammy is coming with us on the Sex and the City fan cruise. And so I totally told her before we were gonna do this in a different order. So now she's gonna be like, what? So go ahead and tell us as the gay and lesbian matchmaker, what special things you're gonna offer to all the people who are also in this group and on the ship in general. This could be so cool.

Tammy Shaklee:

In the industry, some joke can call me the fairy gay mother that I've done this for so long. And so anytime I'm anywhere, it doesn't matter if we're traveling, if I'm in the local grocery store, whatever the situation. If I see a potential single, I'm the type that walks up and says, I'm a matchmaker. Are you currently single? Without shame, because I think I have the greatest job in the world. And so I can see, even though my husband and I are gonna be together on this cruise, I can see that I I don't turn that off. If I see someone at happy hour by themselves, if I see someone in line getting their morning coffee by themselves and they order your coffee for 1, not for 2, I will hesitate to say, Hi, The Matchmaker. Are you currently single? Are you on this trip alone? And so my goal, and you know the ship better than I, I'm so excited to see this. And I love an adult's family cruise, but I love the opportunity that we designate a day, time, and space that, you know what? I'll be your wing woman.

Tammy Shaklee:

You show up. It doesn't matter if you're by yourself or maybe you're traveling with your aunt or your sister or your mom, show up, I'll introduce you around. It's not intimidating. I've got you. And even if you make a new friend and you can go on excursion with them the next day because we helped make that introduction, I'll be glad to do it. So I hope to be the spontaneous wing woman on the ship, but we'll have it designated whether it's, I don't know, a piano bar, you know, the space. Let's all try to meet there every evening at 9. If there's 2 of us that show up, that's great.

Tammy Shaklee:

If there's 20, we're gonna make that happen too. And ideally, it will have legs of its own, and it will naturally happen throughout that 7 days together.

Michele:

I'm so excited. I'm so excited. And one of our speakers, Richard, is a member of the gay community and he is coming with his partner, but I think he's gonna really enjoy meeting you and talking to you even though he is coupled up. I think that the 2 of you are gonna have a lot to just chat about.

Tammy Shaklee:

Oh, I look forward to it. Even when I make meet couples, long time couples, really solid couples in the LGBTQ community, My question is always, how did Jimmy watch your story? Everybody has a story and it's not all roses and rainbows. It really is, well, we met and then we were friends and he was seeing someone else, but we're together today. And I think that's inspiring to all singles. It's not this beautiful rom com Disney love story. It really is just real life. I've got a story. You've got a story.

Tammy Shaklee:

Everyone does.

Michele:

So you like, the minute I told you that I was doing this and first of all, you couldn't believe that Molly was coming, so yay. Yay me for being able to surprise you. But, like, the next day, your husband, mister h four m, was calling me and saying, we're booking. We're doing this. Like, you didn't really hesitate. So, I mean, I wish I could duplicate that magic. So please tell me why that was.

Tammy Shaklee:

Oh, I know exactly. Because we have a 15 year age difference, and we've been married for 15 years. And so he's more in just like Sex in the City.

Michele:

I love that.

Tammy Shaklee:

It's just us 2. And so we don't make plans to travel. What we have found is travel finds us. So the year prior, a couple that we know from Sao Paulo, Brazil had just done an amazing trip on a ship in Egypt. And we said, that looks amazing. And then I see a trouble buddy saying, hey, 2 couples have backed out. There's 2 suites left on this last minute trip. And we went because we can be spontaneous.

Tammy Shaklee:

I can run my company from anywhere, and we do love international travel. So, when you said, Hey, I kind of want your advice about this trip. I'm putting together this Sex and the City fan cruise in Greece. I said, well, I'll be at the beach tomorrow, but call me. I wanna hear about it, and I'll give you my just instant advice, thoughts about it. And by the time we were off the phone, I was telling my husband, we are so going on the streets. I said, oh my gosh, you know Molly Rogers, you listen to me watch in Just Like That. And I just, I glued myself to that Lincoln commercial every single time.

Tammy Shaklee:

It's so brilliantly done in her words, in their curating costumes and the headpieces. I mean, we've all watched it. I don't know. I mean, fewer than a 100 times. So when you said her name, I was like, no. No. I feel like I know her from it. That one commercial that we'd watch over and over.

Tammy Shaklee:

And then Cindy Tupac, is that how you say her name? Tupac. Tupac. She is from Little Lim.

Michele:

Yes. Yes, she is.

Tammy Shaklee:

So she and I are gonna geek out about that. And then Richard and his partner, I just I look forward. To me, this is 3 sets of amazing conversations that we can have for the whole 7 days, whether we run into each other at coffee, whether we sit together at dinner or when they have their moment, talk about the shows. I'm so excited. It was a no brainer for me. I didn't know how many suites or rooms you had to book, but I wanted in on the ground floor.

Michele:

So you sat in on the call with Molly, which for my new jetsetters who might not have heard it, I will put that link in the show notes to that particular show where Molly came on. But she gave us some styling tips for our excursion. So explain that to all the listeners, Tammy, what we're doing and what her little tips were.

Tammy Shaklee:

Well, I will tell you, she talked about the shopping trip that we're planning to do. And so I'm not a big shopper at all, and I won't be intrusive, but I could shadow her in watching her pick out or identify or alert to style, or I've never seen that before, or you can only see this on this stuff. I wanna see how the magic works because I'm just not a shopper, not online and not in person. I've always had a stylist. So to watch her do that magic, that's amazing. And then when I discovered the flying dress photo shoot

Michele:

I can't wait for that. I'm so excited for that.

Tammy Shaklee:

I am beside myself because when else I don't know if I'll be back to Greece. And to be able to do that photo shoot in your fifties and be proud of who you are, what you are, what you've become. It's not about having the perfect body. It's not about having the perfect skin or shape or whatever. It's about celebrating who you are at this age. And I think Molly just has that aura about her and makes it happen for other people. So I'm just geeked out about all that. And to go into someone's home and maybe do a tasting or the different wine, because my husband's a wine geek.

Tammy Shaklee:

I wanna be comfortable. I've already been shopping for my comfortable walking shoes, but I wanna be stylish because I want every photo captured in every excursion to be memorable, not a US tourist, but an international enthusiast to have this once in a lifetime experience.

Michele:

Yes. And so we know that we have already had that whole conversation about what do we need to do for scarlet night. And again, mister h for m was on top of it. He was emailing me, like, what is this night? What do we need to do? So have you planned out your scarlet? Because I may have found something just this morning. Maybe. Cause I wanna be able to get in the pool with it.

Tammy Shaklee:

Here's what I'll say. I'm the woman that we eloped to Saint Lucia, and that was a major international trip for us. But we stayed at Jade Mountain on the top of Saint Lucia and it was just the 2 of us. We eloped at a lovely little ceremony on a private beach and I ruined the dress. That was back when ruining the dress was starting to phase. So, to ruin the fabulous dress with a fabulous memory and great photos, I'm all about it. So he and I used our double pointed Nordstrom's day and we indulged in all things red and things that I don't mind ruining. Neither one of us really wears a lot of bread, but we did.

Tammy Shaklee:

And he went all out for pajama night.

Michele:

Very cool.

Tammy Shaklee:

Get ready to meet my Hugh Hefner. Whether you liked him or didn't, he had style when it came to pajamas, even if it was pajamas I'm like. So my hubby has spent more than we have ever spent on pajamas for him to have a debonair look. So I think that's the night he's most excited about.

Michele:

Cool. That's the very first night. That's the very first welcome is pajama night. I should have asked Molly about pajamas. It totally slipped my mind. I was so busy talking about the flying dress shoot. Anyway, so real quick before I let you go, I remember when And Just Like That season 1 hits, and I was not in a great mental place.

Tammy Shaklee:

It was a rough start.

Michele:

Yeah. And then I remember you and I connected. It may have been working for you at that time. I don't know. But I remember we had a conversation where I was like, don't watch the first episode. Do you remember this?

Tammy Shaklee:

Yes. And I heard rumors. I was not doing a spoiler alert. So here's what I did because I'm big on mental, emotional, physical, spiritual health and wellness for my own self and my clients. I've got to be healthy so I can support my clients.

Michele:

And your friends. I mean, you've been a huge supporter of mine.

Tammy Shaklee:

Yeah. And all friends and family, we all have to be there for each other. And so I would not watch the first episode until the second and maybe the third were available so that I could race to the next episode. So I waited to start the series for my own health because I, not an empath, but I do take on emotions pretty hard if someone's going through something in real life, like, you're in our high rise condo or whatever. And so I really have to have that, something to look forward to very quickly so I don't go in a slump. So that was good advice. And and 2, before we go, I wanna mention

Michele:

Before we get to the book that she's holding at that you listeners can't see because this is an audio format, I just wanted to see. So those kind of quote water cooler conversations that we used to have about the original series, because we didn't have social media. We didn't have Zoom. We didn't really even have iPhones back then. We used to gather at the water cooler in the hall and talk about, did you see Harry's outfit, or can you believe she's back with Aiden? Like, all those conversations, and I feel like that's kind of what we did around the first episode of And Just Like That too. And I personally put this trip together because I can't wait to have those conversations again. I feel like to have the water cooler conversations again in person and to pick out our favorite episodes and just like the little hymns chatting. I can't wait for all that.

Tammy Shaklee:

And if you listen to Richard's podcast with

Michele:

Michael Patrick King. Yeah.

Tammy Shaklee:

Michael Patrick King. Well, maybe this is a spoiler alert, but listening to Richard's podcast, when he said he knew what the last episode was going to look like, and then he backed up to get to that in Greece. I was like, wait, what? That never hurt to me that writers work that way. That you go to the end, and then how did we get there? And in that podcast, he said something I misheard in the last episode. I might get a break

Michele:

For good behavior.

Tammy Shaklee:

But it sounds like he said from good behavior. Oh. Oh. So go back, listen to the podcast. He says it twice.

Michele:

We will put it in the show notes. We'll link to that episode of the podcast in the show notes. It's Vanity Fair still watching.

Tammy Shaklee:

Yeah. And I wanna ask Richard about that. Does it mean time frame good behavior or for as a result of good behavior? Anyway, so now I'm intrigued about the next season.

Michele:

Well, and by the time we see Molly, she will already have some of the scripts because season 3 will be in production. So she promised to spill a little bit of tea for us. So maybe she'll let us know if Aidan's coming back for season 3 or not. Okay. You were holding up your prop. So what are you reading, Tammy?

Tammy Shaklee:

So I heard a rumor that this book was being made into a movie. Is there still Sex and the City Candace Bushnell book, copyright 2019, and I found a copy. So that's what I'm currently reading. And then I realized, wait, if it's being made into it, maybe I can Google that. To learn that it's being made into a reality sex and city unscripted dating show in development from creator Candice Bushnell.

Michele:

Wow.

Tammy Shaklee:

So it's women over 50, is there still sex in a city? And that's this year that it's being made.

Michele:

Well, and I know that you watch every dating matchmaking show there is because, of course, you're a matchmaker and we've had this conversation. So we watched Indian Matchmaker together and I say together, meaning we had the water cooler conversations over Zoom and Jewish Matchmaker. Where is lesbian and gay matchmaking series? Is that happening still?

Tammy Shaklee:

Well, here's some scoop. So I've been interviewed now after more than 11 years of doing this. I've probably been formally interviewed, I don't know, 7 times about it and have made a few sizzle reels, and still no one picks it up. The answer being why it's being declined. It sounds too nice. Where's the drama? And I said, there is no drama. I interview the most fabulous, accomplished, loving, caring, generous, intelligent singles, and I introduce them to each other. There is no drama.

Tammy Shaklee:

I don't do drama. My singles don't do drama. So until the industry of unscripted reality shows is about the love and care and concern of singles and our matchmakers, they're not interested in me and I'm not interested in them. So the joke in the office is I'm the Ted Lasso of gay matchmakers. I love it. I'm too nice and nobody believes it. And I'm like, no, really. I baked my client's rum cakes and sent it to it, then I for the holidays 1 year.

Tammy Shaklee:

I mean, I just I love my singles, and I treat them as though they were my siblings and family, and there is no drama. So maybe it'll never be on TV.

Michele:

Though I guess there's dating show in New York where women over 50 is gonna have drama.

Tammy Shaklee:

Well, hot flashes allowed. Don't get me started. I mean, I have a raging psycho than the wrong temperature with the right hot flash. I'm just telling

Michele:

you. And on that note, that was a perfect endnote. So jetsetters, set jutters, I'll be here with you chatting about more behind the scenes great info next week. And until then, have a great time.

Michele:
And just like that, this episode is over. Thank you for joining me. If you've enjoyed today's episode, I would be thrilled if you would follow, like, and share this podcast with all of your like-minded, wanderlusting friends. And, leave a review on Apple iTunes or whichever podcast platform you listen to.