The year was 1997 and former Manhattan Borough President Ruth Messinger was running for mayor. The incumbent was Rudy Giuliani and the potential to make history big..

In an attempt to learn how the voters were viewing her, Messinger convened focus groups who watched as she campaigned in small settings and went around the city meeting New Yorkers.

"The very first comment from a man in the focus group was: well I could tell you that I would never date her,” Messinger told NY1 in a recent interview.

That was only one of the many sexist and misogynist encounters Messinger ran into on the trail that year.

"You felt it a lot, you felt it in comments - can a woman do this?" Messinger said. "On almost every front, New York thinks of itself as being more progressive than it necessarily is. In some areas we are, but in getting women in elected office we're not."

In its history, the City of New York has elected 109 mayors and none has been a woman. For a place that is often thought of as a liberal bastion, the city continues to be far behind the curve when it comes to electing women to office, it's even more notable at the highest levels of government.

But for the first time in at least a decade, there are a handful of women seeking the Democratic nominee to be the city's next mayor, those who have tried to break barriers in the past say many of the obstacles they faced still remain.

"There is lots and lots of sexism in the world, but I would add there is a lot of sexism in government and for candidates," Messinger said.

Those who have come close point to a political system that makes it harder for women candidates but also an entrenched culture and perception about the second toughest job in America.

Former City Council Speaker Christine Quinn, who ran in a crowded primary to succeed Mayor Michael Bloomberg in 2013 said the upcoming election will be a test to see if the same barriers Messinger and her faced still remain in place.

"Look, it is hard to run for office in New York City regardless of your gender, but it is harder if you are a woman,” Quinn said. “That is not only my experience, it's the experience of women who have run and those who are running now.”

There are currently three women running in the primary race to succeed Bill de Blasio: Former Sanitation Commissioner Kathryn Garcia, former counsel to the mayor, Maya Wiley, and former CEO executive, Dianne Morales. Recently, Loree Sutton, who served as commissioner of Veterans Affairs announced she was withdrawing from the race.

"I think there's been an improvement over the last eight years but I think this mayor's race will tell." Quinn said.

While on the trail, Quinn was met with a similar barrage of attacks faced by Messinger years prior. She was criticized for being loud, for her brash attitude and her looks. Today she regrets listening to some of the criticism as she sought to adjust during the campaign.

"I made a huge mistake; I tried to be more palatable. I tried to be less aggressive, less of a woman, less of a lesbian, less of myself and voters are smart," Quinn said. "They can sniff out somebody that is not being authentic in a hot second."

Other major cities have been ahead of New York by decades. Chicago and Houston elected their first female mayors in the 1970's and 80's and they've made steady progress ever since.

Women run 27 of the country's 100 largest cities, that includes Lori Lightfoot in Chicago, Muriel Bowser in DC, Latoya Cantrell in New Orleans and Keisha Lance Bottoms in Atlanta only to name a few.

"We can try and rationalize it – well, it's a bigger job than Chicago or Houston, well it's a bigger city," Messinger said. "I just think people can’t see a woman in that position, New Yorkers don't seem to have a great deal of expansive thinking."

There are some New Yorker women who have broken barriers.

In 1968, Shirley Chisholm became the first Black woman elected to Congress. She became the first African-American candidate for a major party's nomination for president; she was also the first woman to do so.

And there was Bella Abzug, a force in city politics, known for her wide-rim hat and staunch defense of women's rights. She would take on President Nixon, the Vietnam War, and later a campaign for mayor in 1977.

There are also many powerful women in top office, most notably Senator Kirsten Gillibrand, State Attorney General Letitia James and Lieutenant Governor Kathy Hochul, who has been in the spotlight as scandal embroils Governor Cuomo.

For now, whether the glass ceiling will be shattered at City Hall remains to be decided by voters. That primary election is in June.