Gus, Harry, and Archie are three nominally happy husbands with families in suburban New York. All are professional men, driven and successful. The three of them have known each other since their school years. They have grown up together and have now had enough time to discover that their youth is disappearing and that there is nothing they can do to preserve it. They are shaken into confronting this reality when their best friend Stuart dies suddenly and unexpectedly of a heart attack.
After the funeral, they spend two days hanging out, playing basketball, sleeping in the subways, and drinking, including an impromptu singing contest at a bar. Harry goes home, has a vicious argument with his wife, and decides to fly to London. The other two decide to go with him.
They check into an expensive hotel, dress in formal clothing, and meet three young women at a gambling casino. They go back to their rooms with the women. Gus pairs off with Mary, Archie with Julie, a young Asian woman who appears not to speak English, and Harry with Pearl. However, their efforts to hook up with these women are awkward and unsuccessful.
Gus and Archie return to New York, but Harry stays behind. Gus and Archie express concern about Harry and what he will do without them.