Robert/Bobbie
The central character, a (seemingly) happy single man/woman who enjoys spending time with his/her married friends. His/her 35th birthday is the impetus for the story.
- Affectionate Nickname: Is called every variation of the name 'Robert' at some point throughout the play: Robert, Rob, Robbie, Bob and Bobby. Also multiple characters call him 'Bobby Baby' and 'Bobby Bubbe'.
- Ambiguously Gay/Ambiguously Bi: A very common interpretation of his character. He openly admits to having "experimented" with homosexuality despite otherwise being ostensibly straight. In fact this concept was to be the basis of the William Goldman penned '90s film adaption but it never came to fruition.
- This is almost outright confirmed as Bobbie is shown swiping right on a woman in the 2020 revival.
- Chivalrous Pervert: Some see him as this. Has very strong and emotional friendships with women and at the same time is a womanizer.
- Commitment Issues: To an extreme degree.
- Friend to All Children: Specifically mentioned to be "seven times a godfather" and at one point offers to take Jenny and David's kids to the Zoo so they can have some time alone.
- Gender Flip: The newest run of the show interprets this character as a woman.
The Couples
Sarah and Harry
A passive aggressive couple who are highly competitive with each other, as well as suffering from dependence issues with food and alcohol respectively.
- Passive Aggressive Combat: Apparently the basis of their relationship.
- Slap-Slap-Kiss: Their relationship is occasionally shown in this light when it's not just seen as Awful Wedded Life.
Susan and Peter
A slightly eccentric couple.
- Ambiguously Gay/Ambiguously Bi: Peter hits on Robert pretty slyly after getting him to admit that he too has tried same sex relationships. Robert laughs it off.
- Amicable Exes: They get divorced, much to Bobby's shock, but the idea that they would then live apart completely baffles them and they continue to be in a romantic relationship.
- Polyamory: Appears to be their new existence after divorce.
- Southern Belle: Susan in the original script, with the switch of the dialogue in the updated script Peter comes off more this way than Susan.
Jenny and David
- Wet Blanket Wife: Elements of this are played with with different portrayals of Jenny.
Amy/Jamie and Paul
An engaged couple, getting married at last after being together for quite some time, Amy/Jamie is neurotic and prone to histrionics but Paul is devoted to him/her.
- Adaptational Sexuality: Jamie and Paul undergo this in the modern adaption of the play.
- Commitment Issues: Amy/Jamie has severe commitment issues, however unlike Bobbie, hers/his are more related to her/his feelings of not being good enough for anyone, especially Paul.
- Gender Flip: Amy becomes Jamie in the newest version of the show, making he and Paul a gay couple.
- Nice Jewish Boy: Paul is one of the most genuinely nice and positive characters in the play and is utterly devoted to Amy/Jamie despite their neuroses.
- Platonic Life-Partners: Jamie and Bobbie, can also border on being Gay Best Friend. Bobbie even proposes a platonic marriage with Jamie at one point.
- Straight Gay: Jamie and Paul don't fall into any gay stereotypes.
Joanne and Larry
An older couple, very into the New York city life. Larry is Joanne's third husband.
- Deadpan Snarker: Joanne's character to a T.
The Girlfriends/Boyfriends
April/Andy
- Brainless Beauty: And is unusually self-aware unlike many of this trope.
- Sexy Stewardess: Most interpretations of her.
Marta/PJ
Kathy/Theo
