Andrew Yang, the former presidential candidate and leading contender for mayor of New York City, met with a prominent L.G.B.T. Democratic political organization on Wednesday to seek its endorsement.

It did not go particularly well.

In an interview with the Stonewall Democratic Club of New York City, Mr. Yang cited gay members of his staff as apparent evidence of his openness to the club’s concerns, and expressed enthusiasm about the prospect of visiting Cubbyhole, a storied New York lesbian bar, participants said.

He proactively talked about resurrecting the city’s Pride March, but failed to pay sufficient heed to more substantive issues they were actually concerned about, including homelessness and affordable housing, they said.

The club is arguably the leading L.G.B.T. club in New York City, according to Christine Quinn, New York City’s first openly gay City Council speaker. Its members, she said, are politically “sophisticated.” Yet Mr. Yang’s appearance struck those members as pandering and tone deaf, according to interviews, a video and a copy of the comments that unfolded during the virtual meeting.

“I genuinely do love you and your community,” he said, according to a partial recording of the remarks, describing his affection for the L.G.B.T.Q. community. “You’re so human and beautiful. You make New York City special. I have no idea how we ever lose to the Republicans given that you all are frankly in, like, leadership roles all over the Democratic Party.”

“We have, like, this incredible secret weapon,” he added. “It’s not even secret. It’s like, we should win everything because we have you all.”

According to limited public polling as well as private polling, Mr. Yang has surged to the front of the mayoral pack, fueled by his name recognition and celebrity status, as well as his cheery demeanor and optimistic discussion of the city’s future. But in the past, he has struggled with issues of tone: His presidential campaign has been trailed by allegations of a “bro” culture; in one of his own books, he admits to having named his pectoral muscles, Lex and Rex.

A woman now running for Manhattan borough president has also claimed that Mr. Yang had discriminated against her on the basis of gender when she worked for him at his test prep company, allegations that he has consistently denied.

While Mr. Yang has a consistent lead in the polls and has acquired a handful of endorsements from elected officials, he has generally failed to win significant support from New York City institutions, including labor unions and the Stonewall Club, which did not endorse him.

For the first time this year, New York City voters will be able to rank up to five candidates in a mayor’s race. On Wednesday, the club’s board voted to endorse a slate of three: In first place, it chose Scott M. Stringer, the New York City comptroller; followed by Dianne Morales, a former nonprofit executive; and Raymond J. McGuire, a former vice chairman at Citigroup.

Ms. Quinn, who was a longtime club member but was not present at the endorsement interviews, said that while people “appreciate diversity in representation and staffing,” club members have “a long and diverse agenda and want that spoken to.”

Multiple participants described Mr. Yang’s remarks as offensive, saying that members of the club who raised policy issues found his mention of gay bars off-putting.

“Gay, gay, gay. Wow,” one person wrote in the chat accompanying the forum, which was later shared with The New York Times. “More to us than just that.”

To Harris Doran, a club member and filmmaker, Mr. Yang’s insistence on referring to members as “your community” particularly stung.

“He kept calling us ‘Your community,’ like we were aliens,” Mr. Doran said.

Sasha Neha Ahuja, one of Mr. Yang’s two campaign managers — both are gay — said she heard at least one other candidate on the call use the same term, and suggested that some members had gone into the interview process with their minds already made up.

“I hope Andrew continues to have space for folks to listen with an open heart about the experiences of all communities that have been deeply impacted by years of oppression,” she said. “I apologize if folks felt some type of way about it.”

Mr. Yang’s interview was one of nine the club held Wednesday night, before it held its endorsement vote. He was unlikely to win an endorsement, given the club’s longstanding relationship with Mr. Stringer, but Rose Christ, the club’s president, said Mr. Yang could have delivered a performance that avoided the ensuing outcry.

“There were questions and critiques raised about each candidate, but I think it was the tenor with which he addressed the membership that stood out from the other candidates,” Ms. Christ said.

She added that it felt “outdated.”

To some Stonewall attendees, Mr. Yang’s appearance only fueled concerns about whether he can discuss the problems at hand with sufficient depth and seriousness. More broadly, the reaction speaks to how polarizing Mr. Yang’s personality can be — eliciting sincere enthusiasm and disdain in seemingly equal measure.

“When I see a candidate come in just with Michael Scott levels of cringe and insensitivity, it either tells me Andrew Yang is in over his head or is not listening to his staff,” said Alejandra Caraballo, a member of the organization, referring to the character played by Steve Carell on “The Office.” “Those are both radioactive flashing signs that say he is not prepared to be mayor of New York.”

Ms. Christ said members were offended that Mr. Yang chose to focus on bars, parades and his gay staff members.

Those are not the substantive issues that our membership cares about and it came off poorly,” Ms. Christ said.

Michael Gold contributed reporting.

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