For as long as there have been movies, music and magazines, there has been the single gal.
Over the years, she has gone from being a punchline to a glamorous, independent icon. Artists like Beyonce Knowles champion "Single Ladies," and movies like "Something New" make the case for successful, single women maintaining high standards.
But in reality, one group of women has found it harder to leverage professional success into the model personal life.
Over the past few decades, black women in America have made historic strides academically and professionally. According to the Journal of Blacks in Higher Education, at least 60 percent of black students who get awarded college degrees are women. Black women make up 71 percent of black graduate students.
But the statistics point to another issue: Many of the women are single.
According to a recent Yale study, 42 percent of African-American women have yet to be married, compared to only 23 percent of white women. There's also a gap in numbers. The 2000 U.S. Census counted 1.8 million more African-American women than black men.
But is the successful, single black woman a matter of statistics, or are there other more controversial factors at hand?
"Nightline" tackled the phenomenon in a piece originally reported by ABC News' Linsey Davis in late 2009. The piece sparked an outpouring of praise and criticism. Some viewers praised "Nightline" for covering an overlooked issue, while others found the topic offensive.
"It is an issue. I'm sorry," said Sherri Shepherd, co-host of "The View" and author of "Permission Slips." Shepherd headlined a panel of successful and single black men and women to debate the issue in the "Nightline Face-Off": Why Can't a Successful Black Woman Find a Man?
Watch the debate on "Nightline" tonight at 11:35 p.m. ET
"I've had people tweet me and go, 'Here we go again, are we still on this topic,'" said Shepherd. "We will always be on this topic, but I like having it because hopefully, I'll learn something." Shepherd, who is 42, is a single mother who is divorced from a black man. She says she needs a man.
CLICK HERE for behind the scenes photos from the Face-Off
"I think for a long time I was like, 'I don't need a man, I'm going to make my own money,'" she said. "Well, I'm trying to raise a boy, and I think he needs a man. ... I would love to have a man in my life to help me raise my son."
Joining Shepherd on the female side was Jacque Reid, star of VH1's "Let's Talk About Pep."
"There are far too many black, wonderful women out there that are single and living alone and have no hope of ever finding a man," said Reid. "And I'd like to give them some hope."
Reid, who keeps her age under lock and key, still hopes that she can find a black man to partner up with.
"I just love how I feel with a black man," she said. "I love black men... I really think that black men and black women need to actually discuss this, and get past all the anger that exists between us."
Both Shepherd and Reid argued that statistics, unfaithful partners, intimidation and stereotypes play a large role in why there are more single black women.
On the other side were two men with an entirely different standpoint.