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How a Classic New York Night Brought Husbands Tom Postilio and Mickey Conlon Together

Tom Postilio & Mickey Conlon

As Frank Sinatra famously sang, the best is yet to come—especially for husbands and business partners Tom Postilio and Mickey Conlon. The couple of eight years married this spring in a small ceremony, but the two are well known in the New York music and cabaret scene. Working together for real estate firm Douglas Elliman, they manage such clients as Barry Manilow, Liza Minnelli, and their wedding host, Michael Feinstein. The two men told us about their magical first meeting, their marriage, and their secret for loving and working together.

Out: How did you meet?

Tom Postilio: We met on Jan. 28, 2008 at The Town Hall (123 West 43rd Street). We were both excited to be there because on the bill was Marilyn Maye—this beautiful cabaret singer, I think she was about to turn 80 at the time—and we wanted to see her. We didn’t know how many times we would get to see Marilyn perform. That was the reason that drew us there that night.

Mickey Conlon: You know those winter days where you just look outside and think all you want to do is crawl under the blankets? I was having one of those nights. Just as I was about to call my friend to cancel, the phone rang. My friend immediately says, “You’re not thinking of canceling, are you?” He reminded it was Marilyn Maye. How many more times am I going to get to see her? So I ventured out into the cold. We all met under the marquee, and I was immediately intrigued.

TP: We clicked immediately. I saw something sparkly in Mickey’s eyes. I spent the rest of the evening trying to get more information about this new stranger who seemed intriguing.

MC: Generationally speaking, there are only so many people who love that style of music. We were two old souls who were thrown together that night.

When was your first official date after that night?

MC: Our first “official” date really started that night. That night had many chapters. We met under the marquee. We watched the show—obviously there wasn’t a lot of talking. Afterwards, we started a conversation and discovered our mutual love of this world. It’s very small, and you know all of the people in it. It was getting late, and our merry little band of revelers was dropping off to go home and go to bed. Marilyn wanted to go to Birdland (315 W 44th Street) to see Tony Bennett, and nobody else was in, so we went together.

TP: Our next date was the following weekend—I think that Friday night.

MC: That first night, though—we really had our first, second and third dates all in one night. We ordered a couple of scotches, we had great music, we had a great conversation. At Birdland, Tom started to quiz me. He made a sweeping gesture of the room and asked, “What do you know about this world?” And I knew I didn’t want to screw up this question. I was thinking, “Do I need to name everyone in the room? How deep does he want me to go?” He saw I was hanging on the question, so he simplified it. He said, “What do you know of Frank Sinatra?” This was an easy one. He was throwing me a softball. That just goes to show that actively dating can be hard, so when a moment sneaks up on you like ours, you got to take it.

Tom Conlon & Mickey Postilio

Well that’s certainly convenient—to get three dates’ worth of connection in one evening!

MC: And it’s a lot cheaper! (Laughs).

So how long have you both been together?

MC: We’ve been together for eight years, and we were married in March. We’re essentially newlyweds, even though we’ve been together already for some years.

How has life been different since the wedding?

TP: Every time I look down and see a wedding ring on my hand, I feel extremely grown up. It’s amazing to see, when people learn the news, just the outpouring of love and support from people from all walks of our life. It’s just not something I would have imagined when I came out 25 years ago.

MC: The weight of our relationship became more permanent. Not that we didn’t feel it was permanent before. It just felt like somebody had tapped some magical wand over our heads and we were suddenly—united. The funniest thing—we were watching the finale of Downtown Abbey and there was a wedding and I welled up in a way that I hadn’t before. We’re getting married.

You’re married, but you also work together. How do you balance the personal and the professional demands of your relationship?

MC: When we talked about that leap, we didn’t go into it lightly. We laid down some ground rules. No. 1, we have to work as equals. Otherwise it doesn’t work. No. 2, the relationship comes first. If it puts a strain on the relationship, we go back our separate ways professionally. Real estate is not a nine-to-five job. It’s long hours. It’s often a seven-day work week. And when we get home and there’s still something left to do, we understand. If we’re tired or we haven’t eaten, we’ll fix that together. Instead of other couples where one gets home at 6 and the other at 10 and complains that dinner’s cold or a meeting ran late. It just made us better at what we do

TP: We really do put our heads together to solve every problem, every day. It’s very valuable—the power of two.

MC: What we didn’t realize is that by combining forces, not only did we grow our business it grew our relationship. I think our relationship is comforting to clients, too. People in this business move around from one company to the other. They look at us and think, “This is good, they’re working on my listing at midnight or when they get up.” And it’s actually true.

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