Breaking Down This Week’s Insufferable New York Times Marriage Announcement: April 8

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Breaking Down This Week’s Insufferable New York Times Marriage Announcement: April 8

I jokingly started singing that song from Rent at my desk the other day. You know, the “525,600 minutes” song. I was forced to see that play when I was in high school and I’ve had that stupid song stuck in my head ever since. So it should come as no surprise that I hate Broadway. A lot. Which makes this week’s marriage announcement particularly miserable for me considering their affinity for it.

As always, original text in quotes.

* * *

Off Broadway, Showmen Seal Their Biggest Deal

Like so many of the classic Manhattan love stories, this one involves real estate, and a Broadway tune.

The only Manhattan love story I know involves two rival bookstores and a Cranberries song. Yes, I’m talking about You’ve Got Mail.

Those are the twin passions of Tom Postilio and Mickey Conlon, who grew up a dozen miles apart on Long Island, both immersed in the music of an older generation.

Tom and Mickey? Alright, let’s do this, my dudes.

Eventually, they found their way to each other, meeting for the first time under a theater marquee and joining not only their soundtrack collections but their careers, as luxury residential brokers. Their clientele — and social circle — includes Liza Minnelli, Barry Manilow and Joan Collins; they are among the most notable sellers at Douglas Elliman, with cumulative property deals in the billions, and have their own spotlight as stars of “Selling New York,” a reality show on HGTV.

I’ll just come out and say it — I don’t watch “Selling New York” so don’t jump down my throat when I’m completely ignorant to these guys.

But seriously, how “luxury” are you when your social circle was last relevant in 1984? Liza Minnelli? Barry Manilow? Joan Collins? Sure, I like “Copacabana” as much the next guy but the idea of hanging out with them just made me cough from the musty smell I just got a whif of.

Dapper, handsome, with the crisp manners and suave wit of MGM-era heroes (think Cary Grant or Fred Astaire), they’re adept at making others feel at ease, said their friend Christine Ebersole, the Tony-winning actress and singer. “When you’re around them, you just think anything is possible,” she said.

If I were a gay dude, I’d definitely aspire to be described as “dapper, handsome, crisp, and suave” type. Like that’s peak relationship goals no matter your sexual preference. But real talk? I fucking hate Broadway and I hate the Tonys.

The musician Michael Feinstein, a close friend who listed his 18-room home for sale with them a few years ago, noticed their spark right away. “Sometimes you see a light in someone’s eyes, and it’s a subtle change at first, and then it manifests more and more as two people are together,” he said. Couples, he added, find an emotional equilibrium, but it can be low as often as high. “With Tom and Mickey, they truly elevated each other,” he said.

I’m all about wasting money if you’ve got a surplus of it, but who the fuck needs an 18-fucking-room home? Come on, Feinstein. Take your head out and be reasonable with your money. Once you start reaching double-digit bedrooms, at what point are you like, “Dude, I need eight fucking more.” Asshole.

Theirs is a life purpose-built for duets: “Me and My Shadow” is their signature. To their friends and audiences, they are always Tom and Mickey, never Mickey and Tom, with trademark bow ties for Mr. Conlon, and straight ties for Mr. Postilio. If their romance were a musical, we’d see it developing in tandem across the stage, with just the slightest hint of a twist near the 11 o’clock number.

I wanted to like these dudes. I really did. But the combination of these Broadway allusions and the bow ties are just not doing it for me. I’m the type of person that leaves church when it’s a music-only service, so the idea of paying money to go watch that shit on a Friday night is just nappenin’.

Meanwhile, bow ties? Didn’t those die when frat stars stopped thinking pastels were cool? Yeah, you wear one with a tux, but put that shit away when you’re not at a black tie event.

By the time Mr. Postilio, 46, moved to Hauppauge from Queens with his family in high school, he already had throwback tastes. “While everybody else was listening to Guns N’ Roses and Def Leppard, I was running around in Frank Sinatra T-shirts, singing ‘Strangers in the Night,’ ” he said. In 1984, his family had gone to see Sinatra at Carnegie Hall. “For a 14-year-old from Ozone Park, Queens, it was like being hit by a lightning bolt,” Mr. Postilio said. His father, Leonard Postilio, faithfully indulged his obsession by taking him to Sinatra conventions, while worrying a bit about where this fandom would lead.

Alright, I feel Tom’s pain here. Wearing Sinatra shirts while everyone else is going through their hair rock phase is like the time I wore an Armani Exchange t-shirt in gym class in middle school. I immediately got blindsided by a dodgeball by a dude on the football team and never wore it again.

But his son had an angle: He sounded just like Sinatra, or as alike as a teenager could. He began entering and winning singing competitions and, at 20, was hired as a vocalist with the Glenn Miller Orchestra. He earned an associate degree at Suffolk Community College and left to tour the world with the band.

Is that really the trajectory of Suffolk CC? Just graduating and immediately touring the world? If so, that’s incredibly impressive stuff for a casual community college.

For more than a decade, Mr. Postilio lived by the Great American Songbook, singing on cruise ships and with symphony orchestras. He released two albums and had an 18-month run in the Off Broadway revue “Our Sinatra.”

Ohhh, okay. So by “traveling the world” they actually meant performing on a cruise ship. HUGE difference.

“One thing I admire about Tom,” his father said, “he has that stick-to-it-iveness.”

Well, yeah. All his boys say that he puts out an “anything is possible” vibe, pops.

Meanwhile, Mr. Conlon, 39, the youngest of three, was raised in St. James, where he too developed out-of-sync favorites. “I would do Al Jolson impressions at 7 years old,” he said, and “run home to watch ‘Singin’ in the Rain’ if it happened to be on TV.”

I was playing street hockey and trying to mimic Adam Banks and these dudes were imitating all-time great singers? Were these guys raised as snobs or was I just blue-collar as hell? The correct answer is probably, “both.”

And by his teenage years, he was already an adept entrepreneur. At 16, with his mother, Mary O’Rourke, as a co-signer, he opened an antiques shop in town. He took her to auctions, she recalled, where he knew just what to scoop up and resell for a profit. “He always had an eye for that,” she said.

Who the fuck opens a fucking antique shop at 16? Isn’t that what you do when you’re retired and bored? I’m not one to call Mickey’s mom a liar, but I think she’s embellishing here. No way this kid had the chops or an eye for that type of shit.

At 18, he got his real estate license, showing classic homes in his first summer off from Duke University. He had wanted to be a lawyer (he studied political science) but had a change of heart when he also discovered theater producing in college, a way to bridge his business acumen and his showmanship.

Mickey is officially a try-hard, which isn’t all that surprising considering he chose to go to Duke. Antique store at 16? Real estate license at 18? Poli-sci at Duke? Get off your high horse, bro.

Back in New York, Mr. Conlon worked on musicals like the Tony-nominated “Jane Eyre” and “Xanadu,” but the 2008 recession made him rethink his trade, and he rebounded to real estate. Mr. Postilio had landed there, too, after his singing gigs dried up in the early 2000s. He was a founder of a boutique brokerage firm and began appearing on “Selling New York.”

Jane Eyre? How boring is he trying to be? If you’re interest in antiques and Jane Eyre, you best get out my squad real quick because I’ll be asleep and drooling on the bar by the time you’re done getting your first sentence out.

Though they were professionally successful, neither felt he had mastered relationships. “I was never much of a serial dater,” Mr. Conlon said. “To that extent, I consider myself shy.”

Oh, really? No one wanted to snatch up a 16-year-old antique mogul? Imagine that.

On the road, Mr. Postilio rarely had time for dating, and when he changed professions, his retro style made him an outlier. One boyfriend openly recoiled from his musical taste. “He said: ‘Can we change the music? I feel like I’m at my grandmother’s apartment,’” Mr. Postilio said. “And I think I broke up with him the next day.”

Hell yeah, Tom’s ex-boyfriend. I’d be so creeped out if I got home from a Tinder date and some dude was playing Chet Baker. That’s just murder-y.

In January 2008, a mutual friend, the entertainment lawyer Mark Sendroff, invited them to the Nightlife Awards, a gala to honor cabaret, jazz and comedy stars. It was a frigid Monday, and Mr. Conlon balked at venturing out, but Mr. Sendroff persuaded him with the lure of seeing Marilyn Maye, the veteran singer, who was almost 80 at the time. He and Mr. Postilio were introduced under the klieg lights of Town Hall in Midtown, a moment both remember lyrically.

The more I read, the more I can’t understand why these guys insist on hanging out with a bunch of old farts. I respect my elders, but at the same time, I’m not trying to hit the town with a bunch of people who eat dinner at 5 o’clock when the early bird special is still in full effect.

Mr. Postilio: “I was mesmerized by the sparkle in his eyes.”

Mr. Conlon: “I thought, ‘Here’s a kindred spirit.’”

Sparkle in his eyes. Kindred spirit. Barf. I know I compared them to a rom-com earlier, but come on. No one actually says those things IRL.

They chatted at intermission and through the after-party, and then Ms. Maye swept them up to Birdland, where Tony Bennett was on the bill. They were already en route to becoming Tom and Mickey. “Our courting period was Town Hall to Birdland,” Mr. Conlon said.

Okay, okay, I take some of it back. Seeing Tony Bennett at Birdland sounds lit.

Their first official date came just a few days later, and long before the year was out, Mr. Conlon had moved into Mr. Postilio’s apartment. (Mr. Sendroff and Ms. Maye, who is still performing, both take credit for the match.)

What are these kindred spirits doing having plastic on their furniture like all the other old people they chill with? Sounds like these bros move fast, though. Moving in within a year? Pump the breaks.

Their families met quickly, too; Mr. Conlon’s stepfather, James J. O’Rourke Jr., died four weeks after Mr. Conlon began dating Mr. Postilio, and Mr. Conlon was touched that Mr. Postilio and his mother, Eileen, came to the funeral. “Suddenly, I had a new support system in Tom,” he said. “I thought, ‘This is a real, grown-up relationship.’”

Um. Well, gonna have to pass on that passage because I’m not a complete asshole. Why you gotta get so real like that, New York Times? I’m trying to do satire here.

Eileen Postilio said: “I liked Mickey right away. It just took off. They’re so alike, my husband called them the two-headed monster. They’re usually on the same wavelength.”

They used to call me “the two-headed monster” in prison. Just kidding, that’d be weird. Always a good sign when someone refers to you as a “monster” though.

Their force multiplied in 2011, when Mr. Conlon, then working at Brown Harris Stevens, decided to join Mr. Postilio at his firm, CORE. (They migrated to Douglas Elliman last year.)

Does anyone reading this column know what any of those firms are? Or am I just so separated from New York culture that I’m ignorant for reading that as a whole different language?

They did their due diligence before teaming up. “We talked to a bunch of couples who worked together,” Mr. Conlon said, and they made a pact that their relationship came first. “We said, ‘If we’re bickering and we take it home with us, we’ll go back’” to separate jobs. But, he added, “instead of taxing the relationship, it made it stronger.”

Working with your significant other? Yeah, that sounds miserable. Granted I work at a frat blog where I wouldn’t want my significant other to be subjected to 90% of our conversations, but still. Separate business and pleasure.

Their entertainment backgrounds are also a major asset: Mr. Postilio has been known to break into song to close a deal. “We always joke that, in the end, it’s all showbiz, kid,” Mr. Conlon said.

If someone broke into song in an effort to close a deal with me, I’d get so uncomfortable. Seeing people sing acapella in close quarters is my own personal hell, and I know I’m not alone in saying that.

Almost four years ago, they bought their first property together, on the North Shore of Long Island, with an eye toward rebuilding it. They had discussed marriage, and on Christmas 2013, standing atop the roof, looking out over Long Island Sound, Mr. Postilio proposed.

Proposing on Christmas? Yeah, real original, homeboy. You get married on Valentine’s Day too? Be original for me just one time.

They envisioned a grand summer wedding at that Long Island estate. But construction stalled, and they decided not to prioritize a renovation over their commitment.

Me? I would’ve waited. If I’m renovating my estate for a wedding, I’m waiting until that shit’s done so I can show it off to my friends. And yeah, I know I’m the person who talked shit about having an 18-bedroom house, but still.

A few weeks ago, they very nearly eloped, asking Mr. Feinstein to be their witness at City Hall. But the calendars didn’t quite align, and anyway, Mr. Feinstein had a better offer: Why not marry at Feinstein’s on the Upper East Side (otherwise known as his house)?

These two were just going to City Hall it? Yeah, in what universe? From what I can tell, these two seem high maintenance, so I don’t exactly see them slumming it at City Hall.

Because Mr. Postilio and Mr. Conlon already host a big annual party for their clients and friends, they chose an intimate wedding. On March 25, their parents and a few siblings gathered in the Champagne-hued, art-filled living room of Mr. Feinstein and his spouse, Terrence Flannery. Ms. Ebersole, a Universal Life Minister, officiated, with Mr. Feinstein at the piano.

I hope someone describes my wedding as “champagne-hued” because I’ma stock that bar with hella bottles. You best believe that.

But shortly into the ceremony, Mr. Postilio began to falter; Ms. Ebersole seated the couple on a tufted banquette, where Mr. Conlon rubbed his fiancé’s back protectively.

Um, red flag much?

Mr. Postilio was having a panic attack. It had happened only a few times before, at other momentous occasions in his life, he said later. In the tumult of organizing the event, he hadn’t quite registered its emotional impact. His brother, Chris Postilio, took him outside for some fresh air.

I’m afraid that I’ll either have a panic attack at my wedding, or I’ll be the dude that cries when his bride is walking down the aisle. Both are terrible looks. No getting around that.

Mr. Feinstein understood fully. He and Mr. Flannery had been together for many years when they were wed, by Judge Judy Sheindlin and Gabriel Ferrer, in 2008. “I didn’t think it was a big deal, and the minute we got up there, it was the biggest deal in my life,” Mr. Feinstein said, adding that weddings can carry a different weight for gay couples. “Terrence and I both felt the nakedness of that, the joy of it, and experienced a level of depth that was a complete surprise.”

How fucking awkward was this for everyone they invited to their “intimate” ceremony? The look on my face would be wide-eyed and jaw-dropping. I get awkward when someone makes an off-color remark at a nice dinner, let alone someone having a meltdown at their own wedding.

After a brief intermission, Mr. Postilio returned, the color back in his face. Smiling, he rejoined Mr. Conlon to a lighthearted chorus of “you’re not sick, you’re just in love,” from Mr. Feinstein. With some words “from the gospel, according to Kander and Ebb,” Ms. Ebersole completed the bond of Tom and Mickey: “How the world can change,” she began in a soft singsong, quoting from “Cabaret.”

Come on. At this point, I’d be trying to slip out the back and beeline it to the nearest bar to take the edge off of all that awkwardness.

“It can change like that, due to one little word — married.
See a palace rise, from a two room-flat, due to one little word — married.
And the old despair that was often there, suddenly ceases to be.
For you wake one day, look around and say, somebody wonderful married me.”

Fuck. I hate show tunes so much.

Image via Unsplash

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Will deFries (Twitter / Instagram) is a Senior Editor at Grandex and the world's foremost authority on Sunday Scaries (Twitter / Instagram).

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