Breaking Down This Week’s Insufferable New York Times Marriage Announcement: January 24

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Some columns almost write themselves. In the case of this week’s couple, Haley and Jack, that statement as never been so true.

As always, original text in quotes.

An Actress and an Agent: ‘What Could Be a Better Match?’

Yeah, because no one in the entertainment industry is known for trying to get ahead by any means necessary.

Ever since his divorce in 2008, Jack Tantleff, a theatrical agent in New York, had struggled to find someone to fill the role of partner in his life.

“Fill the role,” I see what you did there. My fingers are crossed for an Ari Gold-esque attitude comin’ out of Jack for all this.

Then his dinner plans fell through one night in Las Vegas last April, where he had flown to see a client’s production of a musical based on the “Duck Dynasty” reality-TV tribe. He decided to join his fellow New Yorkers Mark Sendroff, an entertainment lawyer, and Hunter Ryan Herdlicka, an actor, for a quick bite.

Yeah, if by “dinner plans” you mean “strip club” because everyone knows that if you’re going to Vegas with an entertainment lawyer for a musical based on “Duck Dynasty,” you’re not not going to a strip club.

“I showed up unannounced, and all of the sudden, this incredibly gorgeous woman walks up to the table and starts saying hi to everybody,” he said, referring to his future bride, Haley Swindal, a close friend of Mr. Herdlicka’s who was performing in “Duck Commander Musical,” which he had come to see.

When I start writing these breakdowns, I know they’re going to be entertaining. I know there will be some gems to make fun of. But having a couple meet in Las Vegas because she’s performing in the “Duck Dynasty” musical is something I couldn’t have thought up in my wildest dreams.

In no time, Mr. Tantleff, now 58, and Ms. Swindal, now 30, were mired in some sassy bickering, sparring good-naturedly over the future of the show.

Because when’s the last time you heard of a 28-year age difference affecting the health of a marriage? Jack and Haley are built to last.

“I was struck by how confident he was in his opinion, not conceited, but he knew who he was,” said Ms. Swindal, who is the daughter of Jennifer Steinbrenner Swindal, a Yankees general partner, and Steve Swindal, a former Yankees general partner and the chairman of the Port Authority of Tampa. The bride is a granddaughter of George Steinbrenner, the late Yankees owner.

Okay, this is all making more sense now. So by Haley being an “actress,” it just means that she’s riding out Steinbrenner’s fortune until she meets someone to marry. Like, oh, I don’t know… a successful agent who’s also a divorcee?

Ms. Swindal left to prepare for the performance, and she and Mr. Tantleff began inundating Mr. Herdlicka, via text and otherwise, with questions.

Mr. Herdlicka seemed to revel in his role as matchmaker.

Read: Five scotches deep, Mr. Tantleff questioned Mr. Herdlicka on whether or not Ms. Swindal would be available after the show, or if he should just go straight to Treasures, the well-known gentleman’s club and steakhouse.

To Mr. Tantleff, sitting in the audience next to him at the “Duck” performance, he whispered: “Don’t you think Haley is really cute? Don’t you think Haley is a great dancer?”

It’s like they’re actually in a strip club.

And to Ms. Swindal while she was backstage, he texted: “Didn’t you think Jack was great? He loved you, and he loved the show.”

Okay, this friend feels a little too into this matchmaking. Like, we get it, bro. These two are into each other. Let it marinate for a bit because you’re creeping everyone out.

Mr. Tantleff, the head of the theatrical literary department of the Paradigm Talent Agency, didn’t need much encouragement. The next day Ms. Swindal walked into her dressing room to find it filled with calla lilies and a note from Mr. Tantleff saying he hoped to see her again soon.

Agents are known for closing deals, and Jack wasn’t about to risk losing Haley to all the other onlookers at this musical. I mean, once you see a skilled dancer at the “Duck Dynasty” musical, everyone knows that you lock. that. down.

“Who is this guy?” she wondered, admittedly intrigued. She consulted Mr. Herdlicka.

“Go for it,” he replied. “He’s successful and he’s perfect. And you’re an actress and he’s an agent. What could be a better match?”

If a relationship starts with “you’re an actress and he’s an agent,” you know it’s a “til death do us part” type of deal.

It was a little surprising that the couple had not met before, because they had attended many of the same events over the years, including a party the night of Ms. Swindal’s April 2013 Broadway debut in “Jekyll & Hyde,” which was directed by Jeff Calhoun, who also directed the “Duck” musical in Las Vegas.

And in November 2014, Ms. Swindal had gone to the performance and cast party for “Side Show,” a Broadway musical for which Mr. Tantleff was the creative supervisor.

Maybe it was because there’s a 28-year age difference and they’re running with different crowds. Think that might be it or…?

But with Ms. Swindal committed to being in Las Vegas for another six months, and Mr. Tantleff living in New York, a date, let alone a relationship, seemed far off.

Come on, guys! True love conquers all! Work this out!

But less than a week later, Ms. Swindal took the red-eye to New York to attend the opening of “Something Rotten!” which she had invested in. And as she went down the stairs at the theater, she ran into Mr. Tantleff going up. He was skipping the after-party and invited her for cocktails. But she had producing partners to entertain and didn’t want their first date to be a late-night drink.

Alright, this seems a little too coincidental, even for a couple as “stars aligned” as these two. They just randomly met on the stairs at a show she invested in? Yeah, right.

Instead, they set a time for a phone conversation and then started texting each night after her show — for Ms. Swindal, 11 p.m. in Las Vegas; for Mr. Tantleff, 2 a.m. in New York. An early-to-bed, early-to-rise kind of guy, he stayed up to talk to her despite the time difference.

I’m sure ol’ Jack was so early to bed, early to rise before they met. Agents are known for living slow-paced lives. Especially in New York.

Then she learned that “Duck Commander Musical” was closing.

Shocker.

Ms. Swindal, who had shipped her car west, had planned a road trip back home with stops at a number of national parks and a memorial — Zion, Bryce Canyon, Grand Teton and Mount Rushmore — with a fellow cast member, Mimi Bessette. On her last day in Las Vegas, Mr. Tantleff sent Ms. Swindal a giant care package of maps, travel games, sunscreen, candy and water.

I respect the care package, but why send her water? Does he not realize they can buy that at pretty much any rest stop or gas station along the way? Seems like a minor detail to be hung up on, but still. Just seems bizarre.

“The whole trip, Jack stayed in touch,” Ms. Bessette said. “I knew she was very excited to get back by the end of the week because they set up a date in New York.”

Well, yeah, they were all horned up for each other. Jack saw Haley dancing onstage night one and hasn’t been able to lock it down since.

On Ms. Swindal’s first night home, Mr. Tantleff took her to Coney Island, where they rode the Cyclone (twice) and kissed atop the Wonder Wheel. The next night, he escorted her to Bemelmans Bar at the Carlyle and crooned “I Only Have Eyes for You” so softly that only she could hear. Afterward, he kissed her in the cab before dropping her at her apartment.

This sounds like cheesy throwback movie from the 1960s starring a couple of the same characters that starred in The Sandlot. Haley legit probably thought Jack wrote the song because she’s so removed from that time period. The only reason I know that song is because I love My Girl.

“I got out of the car and was like, yep, I’m done. Sign me up. I’m good.”

But you didn’t invite him up? Come on. Also, what kind of shitty agent takes cabs? You’re telling me this dude didn’t have a driver when he’s taking out the granddaughter of George Steinbrenner? Weak.

They saw each other almost every day after that, dancing until 4 a.m. at a Tony Awards party and hiking up a volcano during a vacation in St. Lucia.

Look at this Thomas Crown-actin’ motherfucker.

When she and a friend attended “Queen of the Night,” an immersive theater piece in the basement of the Paramount Hotel, a cast member handed her a card and said, “You’re in love.” She opened it to find a poem written by Mr. Tantleff.

The money I’d pay to read this poem. I don’t want to rain on anyone’s parade, but I’m putting it at about a 20% chance he actually wrote that thing.

“They both called me after the first date and after the second, but pretty soon the check-ins stopped, and I knew it was golden,” Mr. Herdlicka said. “They didn’t need affirmation from me.”

No news is good news, Mr. Herdlicka. Everyone knows that.

In October, Ms. Swindal performed “I’ll Hold Your Hand in the Rain,” a song she had composed for Mr. Tantleff as part of “Play to Win,” her solo show at 54 Below, in which she recalled the influence of her grandfather, Mr. Steinbrenner. Some of the lyrics:

I’ll be your shelter

I’ll stand by your side

I’ll wipe away tears that you won’t have to hide

I can’t stop the storm

And I can’t stop the pain

But I can promise you

That I’ll hold your hand in the rain.

I wrote something like that for a poetry competition in 9th grade, but it was deemed “unpublishable” by the other student editors.

“It was the highlight of the night: a young lady in love singing to her fiancé,” said Mr. Calhoun, who was seated next to Mr. Tantleff and caught him wiping away tears. “It was a perfect moment. There were no lies. It was just complete truth.”

This is legitimately ruining the aura of agents for me. What happened to the Drew Rosenhaus types? The sharks? The killers? This dude is just sitting here crying at a musical? Come on.

Mr. Tantleff, a master of grand gestures, had kept it simple when proposing six months after their first encounter, sending her to the refrigerator to retrieve some ginger ale. Discovering a Harry Winston box on top of a can, Ms. Swindal turned to find him kneeling on the kitchen floor.

Harry Winston? This dude is ballin’. Everyone knows a strong engagement always starts with some ginger ale. It was probably to help settle his stomach because he’s 28 years older than her.

“I got on my knees and told Haley that I loved her more than anything in the world, and I would be honored if she would marry me,” he said.

Of their whirlwind courtship, Ms. Swindal said, “I think we’re both very passionate, and it just hadn’t clicked with other people. So when we found it with each other, it was like, why wait? Jack’s very assertive, which I love. He knows what he wants, and he’s confident in it and goes after it. He’s also incredibly thoughtful.”

Oh, and his time is running out. That was a driving factor too. I’m 29 and the thought of re-entering the dating game is scary enough as it is. The older you get being single, the more risk you run just accepting being a future step-dad as someone’s second husband.

Mr. Tantleff, a father of two, said he was struck by Ms. Swindal’s kindness.

I need to know how old his kids are. I need Haley to be younger than his daughter.

On a balmy Dec. 12, the couple were married on the 101st floor of One World Trade Center in Lower Manhattan, where Marci Reid, an actor and friend of Ms. Swindal’s who was ordained by Open Ministry, officiated at a ceremony attended by family members.

Holy shit. Jack changed the game with that wedding location. I knew it wouldn’t be a shitty Brooklyn warehouse like last week, but damn.

Afterward Steve Tyrell, taking a break between a Frank Sinatra 100th-anniversary tribute on SiriusXM and his cabaret show at the Café Carlyle, sang “The Way You Look Tonight,” encouraging the newlyweds to take a twirl and recounting how Ms. Swindal had sung at her grandparents’ 50th wedding anniversary.

Please let there be a video of this.

…

YAHTZEE.

You can smell all the money in that room from here.

Then 250 guests ascended to the 102nd floor, which had been transformed by white flowers and pine trees tipped in silver into a heavenly winter wonderland with the city twinkling far below.

Everyone knows how I feel about off-season weddings.

At 1 a.m., persuaded by friends, Ms. Swindal belted out “Fly Me to the Moon” and “Somewhere Over the Rainbow” with Diva Jazz, an all-female band.

Please let there be a video of this.

…

Dammit. I knew lightning couldn’t strike twice. Especially when this couple has already given us so much gold.

That a pragmatic businessman and a sensitive performer should find love with each other made perfect sense to friends like Mr. Calhoun.

Well yeah, a wealthy agent and George Steinbrenner’s granddaughter who doubles as an actress. We’ve already established this. It’s a match made in entertainment Yuppie heaven.

“I think all of us who are attracted to theater have unique DNA, and it’s very difficult to have a relationship with someone in the arts because of the emotional roller coaster we go through while they’re living in the shadow,” he said afterward. “So when we do find that match, it tends to be very special. Haley and Jack are very special, and very unique.”

I’ll be on the lookout for her shows, which I’m assuming will be few and far between considering she was working on the failed “Duck Dynasty” project and is now married to a well-off businessman.

Best of luck to the happy couple. .

Image via Shutterstock

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Will

Will (Twitter / Instagram) is the host of The Sunday Scaries Podcast.

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