In 1999, The Best Man premiered in theaters to glowing reviews. How could it not? With a plot all about the power of friendship and stars like Nia Long, Taye Diggs, Regina Hall, Morris Chestnut, Sanaa Lathan, Terrence Howard, Melissa DeSousa, and Harold Perrineau, it was impossible not to fall in love with the film.

The group reunited in 2013 for The Best Man Holiday. And now they’re back together once again—this time for The Best Man: The Final Chapters. The Peacock limited series, which is now available to stream, catches up with the friends and shows where their relationships stand now.

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Creator, executive producer, and co-showrunner Malcolm D. Lee says he hopes the series makes audiences feel “warmth, emotion, laughter, and like being with old friends who knew you when, and that you recognize yourself in.”

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As a Black woman who has long considered the first Best Man movie to be one of the greatest Black American films of all time, I’ve been eagerly awaiting this latest installment. Speaking with the cast, I was delighted to discover that they share a real-life bond, too. Here, we asked them for their take on some of the friendship lessons that The Best Man franchise has taught us over time.

Loyalty matters

Diggs and Long—whose characters’ enduring friendship has always seemed like something more—had nuanced responses when asked if there’s anything a friend can do that is unforgivable.

Diggs: I think it differs, and it depends on the type of friend that you want to be, and how badly you are hurt. I can say, looking from the outside into other friendships, I think in a lot of ways, friends bail on each other a little too quickly these days, especially with everybody being canceled for whatnot...so it makes me wonder what people think being an actual friend is. People can have missteps. People make mistakes. I want someone who will stick by me regardless of certain choices I may make.

Long: But here’s the problem: If the friend continues to make the same mistake over and over again, then the trust is gone. And the friendship’s over. I’m not a one-and-done type person. I think I have a pretty big heart. But if I feel that I’m being taken advantage of, or the person is not hearing me, or there’s a sense of entitlement where they feel that they can do whatever they want and I’m going to always be there, then the time has expired. And then I’m gonna call Oprah and say, “Oprah, let me be your other Gayle.”

Check in with yourself

Hall and Chestnut—whose characters are both searching for their new calling and purpose—believe that checking in with yourself at different ages is key.

Hall: I think people are always changing and evolving—so sometimes your purpose has to change as well.

Chestnut: When you talk about walking in your purpose, sometimes I think the challenge is finding out what that purpose is, and then defining it. Maybe in your early 20s, you think it’s one thing. And then [in] your late 20s and your early 30s, it’s something else. Finding what it is at that time in your life and then not only walking in it but being able to redirect when it changes is important.

It’s possible to grow together

When asked if they believe in soulmates, Howard and DeSousa—whose characters have always had an on-again-off-again relationship—shared one way their real-life dynamic mirrors their on-screen one.

DeSousa: I do believe in soulmates. I think sometimes things are just out of your control. I think we’re a perfect example as actors and as characters. Because when Terrence and I first met, we didn’t really get along too well. It wasn’t bad...we just didn’t really connect, put it that way. It’s so funny; the universe kept bringing us back together, and now it’s a soulmate situation. It’s like we were meant to be.

Howard: Now we understand. When we were first blossoming, the buds were growing in different directions as they came up. And now we are facing each other and it’s like, “Oh, that’s what we were supposed to get to.”

This interview has been edited and condensed for clarity.

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Jane Burnett
Assistant Editor

Jane Burnett is an Assistant Editor at Oprah Daily, where she writes a variety of lifestyle content for the editorial team. She's a journalist with a pop culture sweet tooth—when she isn't catching up on celebrity news, she's usually listening to a podcast! Jane was previously an on-air reporter in local news, and worked at Thrive Global, Ladders News, and Reuters. She also interned at CNBC through the Emma Bowen Foundation, and is a member of the National Association of Black Journalists (NABJ).