Producer Spike Lee believed the female lead should have believable basketball skills. Gina Prince-Bythewood said in an interview "I saw over 700 people for the part: actors, ballplayers, people who had never acted before in their life. It finally came down to Sanaa Lathan and Niesha Butler [a star player at Georgia Tech and 1999 Atlantic Coast Conference rookie of the year]. I put Sanaa with a basketball coach for two months and Niesha with an acting coach."
In an interview with the Los Angeles Times, Sanaa Lathan said her basketball tryout was terrible because she'd never played before. "It was so embarrassing because literally I didn't know how to dribble. I didn't know how to hold the ball. But I'm proud of how it looks [in the movie]. I had no idea I would be able to do it."
The scene where the character Monica is pushed and receives a scar was added because Sanaa Lathan has the scar on her cheek in real life.
After playing a smooth-talking player in Waiting to Exhale (1995), Dennis Haysbert was hesitant to play another cheater. He told Jet he took the role because "Then I saw the emphasis was going to be on the father-son relationship. That was something that was close to my heart."
Alfre Woodard has also played Sanaa Lathan's mother in 2 other films: Something New (2006), and The Family That Preys (2008).