Up-and-coming author Harper Stewart (Diggs) travels to Los Angeles for a wedding and is forced to deal with the fallout once his friends start to recognize themselves in his thinly-veiled autobiographical novel. A sequel, The Best Man Holiday, was released in 2013.
- Beauty Is Never Tarnished: Subverted with Mia, who spends most of the sequel looking gorgeous, despite being cancer-stricken. . .until she takes off her wig and reveals that the chemotherapy has left her bald. Even so, she still looks much better than any terminal cancer patient would.
- Birth/Death Juxtaposition: Robyn gives birth just after Mia's funeral.
- Black Gal on White Guy Drama: Actually averted with Jordan and Brian. There's some mild teasing of Brian from the other guys, but their issues stem from Jordan's stubbornness.
- Blood from the Mouth: Mia, indicating how ill she is.
- Expository Hairstyle Change: used for the college flashbacks.
- Happily Married: Subverted with all the married couples in the sequel. While ostensibly happy together, the reunion dredges up some underlying issues and causes tension. [[Regardless, Lance and Mia are the couple with the strongest relationship, but it is tragically cut short as she is dying of cancer]].
- Hypocrite: Lance cheated on Mia left and right, but is so enraged at her one instance of infidelity—which happened as a result of his behavior—that he's ready to call off the wedding.
- Men Don't Cry: Averted by Lance during his wedding ceremony and after Mia's death
- Once Done, Never Forgotten: In the sequel, there is still tension between Lance and Harper over Harper sleeping with Mia, despite it being 14 years since he learned about it and roughly 20 since the incident itself. Similarly, there is friction between Robyn and Jordan despite 14 years since Jordan and Harper almost slept together.
- Reality Ensues: The first film strongly insinuates that Lance forgave Harper over his take in the affair but the sequel showcase that no matter how genuinely sorry Harper is, it will take a long while before Lance would truly forgive him.
- Second Love: Robyn to Harper. Jordan is arguably his first, despite them never having even officially dated.
- Sequel Gap: 14 years between the original and the sequel.