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.
Hill Harper is an actor on "CSI: NY" and author of "The Conversation: How Black Men and Women Can Build Loving, Trusting, Relationships." Harper argued that black woman need to date men who show potential, despite their not necessarily having reached it yet.
"I'm very excited and I think it's going to be pretty lively," said Harper. "We're talking about relationships and we're talking about what's going on in the community and a lot of the things that are in my book."
Harper said that black women and men need to learn how to communicate. The risk, he said, was "destroying the black family."
Author and NPR contributor Jimi Izrael joined Harper on the men's side. Izrael is author of "The Denzel Principal," a controversial book that says black women are searching for a prototypical man who only exists in their imaginations.
"Some of them are delusional or some of them are impatient," Izrael said. "The Denzel Principle is just the idea that some women, not all women, have standards for potential mates as to be so high as to find themselves disappointed when looking for men. Because they are looking for this ideal that couldn't possibly exist."
The debate took place at the Porter Sanford Center for the Performing Arts in Atlanta, a hotbed of black culture, style and professionalism. Co-moderating the debate with "Nightline"'s Vicki Mabrey was Steve Harvey, a relationship commentator and author of "Act Like a Lady, Think Like a Man."
"I'm an expert on the mindset of the male species," Harvey said. "I'm an expert hands down. I understand manhood inside and out."
Almost 1,000 people attended the Face-Off, with as many as 300 people turned away at the door.
"I don't want to go there [as] that bitter black woman. I'm not," said Shepherd, prior to the debate. "I truly want to know what makes black men tick, because if I can figure out what makes you tick then maybe I need to do something differently that's going to make us flow together. I refuse to give in to the fact that there's no good black men out there for me."
"There are single black men too," said Hill Harper. "And they go hand in hand... And they both had different reasons as to why they were single, but it was still, at the end of the day, they're not partnering. [I] wanted to know what's going on and that's really what I wanted to get into this discussion."
Watch the debate on "Nightline" tonight at 11:35 p.m. ET