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Night Out

By KATIE ROGERS

It was cocktail hour on a recent afternoon, and the comedian Chelsea Handler, her brother Glen, and a publicist sat at the bar in Trump Tower, the gilded home and workplace of Donald J. Trump, the building’s namesake and the country’s Republican presidential nominee.

This part of the building is billed as “a stylish and welcoming respite from the bustling Midtown crowds.” But the maroon drapery, dim lighting and fading carpets did not impress Ms. Handler. Nearby, a man with a ponytail sipped a beer, and a small gaggle of tourists wearing sequined tops poked their heads into the bar.

“I feel like we’re at an airport lounge,” Ms. Handler, 41, said in a deadpan. “Like a really bad airport lounge.”

This backdrop is not the most obvious of meeting places for a woman who has used her many platforms — Twitter; her Netflix talk show, “Chelsea”; and, occasionally, her body — to warn the public against Mr. Trump’s presidential ambitions, often in language that can’t be printed here.

Ms. Handler was in town for only a few days last month, and she wanted to squeeze the trip to Trump Tower in between interviews for her show and rehearsals for the Global Citizen Festival.

“I thought it might just be a nice change of pace,” she said, “to see if everybody here is as pumped up about their candidate as he thinks they are.”

Although the building has become the site for rowdy protests in recent weeks, the energy inside during Ms. Handler’s visit could not be described exactly as “pumped up.” Around 5 p.m., shortly before Ms. Handler retired to the bar, the basement food court began to close down and people drifted through the halls, peeking around corners and hovering near the basement bathrooms.

Ms. Handler lingered at the gift shop in the basement, a labyrinth of gold-toned mirror panels and rust-colored marble. “Anytime you use that color marble, you’re covering up for something,” she said.

She perused crystal cuff links (made in China) and candy bars. A shopper in an oversize T-shirt and glasses stood close by, unable to place Ms. Handler. In fact, few people seemed to recognize her.

“You don’t know who that is?” a shopkeeper, Alicia, whispered to the T-shirt woman. “That’s Chelsea.”

Ms. Handler has been in show business for over a decade, with much of her time focused on a celebrity-driven talk show. With “Chelsea,” she has pivoted, in an effort to discuss politics at a time when people’s attention spans are fractured, in part by this bruising election cycle and in part by social media.

She is about halfway through making 90 more episodes ordered up by Netflix. She has used the show not only to explain modern politics to her viewers, but also to explain United States election history.

“I can talk about politics, science and health,” Ms. Handler said at the bar. “About things that actually matter and impact someone’s information in a more palatable way.” I think that’s what I set out to do, and like this is what I’ve wanted to be doing for a while.”

But tonight is about relaxing and enjoying a Handler family pastime: cocktails. You may recognize Ms. Handler’s brother from a recent profile of The New York Times’s most prolific internet commenters. He writes under the handle Socrates and likes to talk about death, spirituality and politics online.

He seems to enjoy these topics in person, too.

“He always makes sure that I don’t believe in God,” Ms. Handler said of her brother.

Mr. Handler said, “We’re all a bunch of ants marching on this planet, and we’re all about to kill each other.”

(To the suggestion that maybe the wrong Handler sibling got the talk show, Ms. Handler responded she was certain her brother would agree.)

The bartender, also named Alicia, told Mr. Handler that Mr. Trump comes here often for interviews and does not drink.

“Red flag,” Mr. Handler said.

“Major red flag,” Ms. Handler said.

Anyone who has read her books or watched her TV shows will know that drinking is a major tenet of Ms. Handler’s comedy. Is it just a comedic device?

“There’s no lore: I love drinking,” Ms. Handler said. “I’m always up for working longer or staying longer or having a longer dinner or having a longer meeting if there’s a cocktail involved. It’s like my Ritalin.”

While nursing a Tito’s vodka with a splash of soda, Ms. Handler ordered a burger — medium well, no cheese — and then picked at the meat. A platter of chicken wings drew her attention. They tasted frozen, she said, but they were ultimately not that bad. After the Netflix publicist turned up with a dish of what appeared to be microwaved peanuts, the group decided to leave.

They headed for the Mark, a hotel on the Upper East Side where Ms. Handler likes to stay when she’s in town. It is here that Ms. Handler’s favorite summer cocktail, an Aperol spritz, was sampled and where Ms. Handler eventually stole away to her room for a few minutes to herself.

While away, she posted a video to her Snapchat account, in which she talked about a book, “Love Warrior,” that made her cry on the flight from Los Angeles to New York.

Another video followed: “Every time I try to be alone I end up with a group of people,” she said. “With drinks.”