Submitted by Tornado Dragon
One night, Brian pays Doug a visit at his new nightclub to ask for a job there, and they soon go onto Doug’s sailboat out back to drink and talk. Moments later, Doug confides to Brian that he and his wife Kerry are broke; due to his lack of knowledge about anything other than serving drinks, he blew all their cash on some bad investments, plus the costs of running his nightclub exceed any expected profits. He also says that Kerry knows nothing about any of this, being too afraid to tell her. He soon passes out from the alcohol, and Brian winds up taking Kerry back to hers and Doug’s apartment when she wants to return there. She tries to initiate a sexual tryst with Brian once they get there, but he halts it before it goes too far and leaves.
Brian returns to Doug’s sailboat in the early morning to check on him and finds him dead from suicide, having slashed his throat wide open with a broken liquor bottle. After attending Doug’s funeral, Brian gets his suicide note in the mail, where he tells him that he killed himself because he felt his life was a sham, and the only thing he will miss about it is the conversations they had. Spurred by this whole unfortunate episode, Brian forces his way into the penthouse apartment of Jordan’s wealthy father Richard to speak with Jordan, where he tells her that he loves her and wants her to come with him while also informing her about his plan to open his own bar in the near future. She decides to go with him against her father’s wishes, since he thinks Brian is nothing but a loser, and he tells them in parting that they won’t get so much as a dime out of him, but Brian replies that that suits him just fine.
Brian and Jordan wed, and Brian opens “Flanagan’s Cocktails & Dreams”, which becomes successful. At the bar one night, Jordan surprises him by telling him that the baby she is already carrying is actually a set of twins, so he tells everyone that the drinks are on the house.
While Brian (Tom Cruise) is tending bar at a resort in Jamaica, he becomes attracted to Jordan (Elisabeth Shue), a woman staying at the resort, and over the next week, the two of them spend a lot of time with each other and even sleep together. However, Brian ruins all of that one night at work when he gets dared by Doug (Bryan Brown) to try to get Bonnie (Lisa Banes), a rich older woman sitting at the other end of his bar, into bed with him, and he takes Doug up on it and is able to pull it off. Unfortunately, while he was walking with Bonnie back to her place to do the deed, he was completely unaware of the fact that Jordan had seen them. The next morning, Brian finds himself regretting what he just did and immediately runs over to the house Jordan has been staying at with friends to confess his affair to her, but he finds out that she left on a flight back to New York late last night. Bonnie visits him at his place later that day and essentially tells him that she wants to keep seeing him, so he decides to become exclusive with her.
The next day, Brian meets with Doug and his new wife Kerry (Kelly Lynch) – whom Brian learned earlier on comes from a wealthy family – on their yacht. After he notices that Doug is keenly following the stock market now, Doug tells him that Kerry’s father has agreed to financially back him on a posh nightclub he is going to open in a couple of weeks in Manhattan, and then he offers Brian the job of being the club’s head bartender. Brian thanks him for the opportunity but says that he has plans of his own; he is heading back to New York with Bonnie because she is going to be hooking him up with her business (hoping that he can get some of his marketing ideas off the ground). Doug bets him a bottle of Louis XIII cognac that he will be working for him by St. Patrick’s Day, and Brian accepts that bet.
After living with Bonnie for a while, Brian finds that her promises of helping him advance in the business world are amounting to nothing because she treats him more like a boy toy/servant. Finally, after getting into a fight with an artist during an art exhibition that she takes him to one night, he breaks up with her. He then finds and attempts to reconcile with Jordan, since he truly does not know why she won’t talk to him, and she ultimately relents and decides to invite him into her apartment one night to give him a chance to explain himself. She tells him that she saw him leave that bar in Jamaica with Bonnie, and he (VERY lamely) tries to justify his actions by saying that Doug had married a rich chick and had bet him that he couldn’t hustle a rich chick himself, and when you get dared, you have to do it. She tells him that she really thought they had something going on, and he replies that he guess he just got spooked at the idea that she might be the right gal for him, but he says that he can handle it now. She then surprises him by telling him that he got her pregnant but adds that she will not burden him with it and he can still go out and become a rich businessman as he wants, then orders him to leave. He asks her why she even bothered to tell him about this baby if this is the way things are going to be between them, and she replies that she knew it was the best way to get him out of her life. Brian then departs, and Jordan starts sobbing.
Brian goes to the bar owned by his uncle Pat (Ron Dean) and tells him about the pregnancy and how Jordan doesn’t want him involved in her life or the child’s, and he asks him what he should do about her. Pat responds by telling him that he doesn’t have to do anything because he is free and clear, but when Brian puts forth the notion that he really does care about her, Pat informs him that he definitely has a problem if that is the case. Brian heads back to Jordan’s apartment to speak to her, knocking on her door repeatedly but getting no response. A female neighbor who overhears the noise then comes out and tells him that Jordan isn’t in there and is actually over at her parents’ place. When he asks where that is, she gives him the address, and he goes there and finds out that that address belongs to a luxury apartment building on Park Avenue, meaning that Jordan’s family is of the well-to-do variety. He gets invited up to her parents’ penthouse and finds himself speaking with her father, Richard (Laurence Luckinbill). Richard is not happy to see him, and when Brian asks about Jordan, he tells her that she is not in, but he would like to talk to him. Richard informs him that he has no interest in letting him discuss anything with Jordan, and he soon offers Brian a check worth $10,000 to just go away. Brian tells him that he doesn’t want his money and he can’t just buy him out of Jordan’s life, and Richard angrily replies that he is not letting some bartender into his family and destroy her life. Jordan then returns, and Brian pleads with her to give a possibility of them having a relationship another chance, in addition to saying that the baby needs a father. She refuses, asking how she is ever going to know that he is being honest with her, for he can barely be honest with himself. Brian points out that she wasn’t being honest with him because she never told him that she was rich, and she replies that he seems so hung up on money that she was afraid that she would never know how he really felt about her as a person. Brian shows her the check and tells her that this is her father’s idea on how to get him out of her life, then he tears it up. He then tells her that what he just did shows just how hung up on money he is, and as for the way he feels about her, it looks like she will never know. He then heads out the door.
Brian pays Doug a visit at his new nightclub with a bottle of Louis XIII and asks him for a job, and he soon takes Brian onto his new sailboat out back to drink the cognac in private. Doug soon confides to Brian that he and Kerry have gone bankrupt; due to his lack of knowledge about anything other than serving drinks and running his mouth, he was unaware of the various costs that come with running a nightclub, which apparently exceeds any expected profits. What’s worse, he has blown all of his and Kerry’s cash in the commodities market. He also tells Brian that Kerry knows nothing about any of this, obviously being too afraid to tell her. Kerry then comes into the boat to see him and says that she wants to be taken back home, but he soon passes out from the alcohol, so Brian ends up giving her a ride. When he gets her inside her apartment, she tries to initiate a sexual encounter with him, but he halts it seconds later, telling her that he cannot sleep with his best friend’s wife. Upset over being turned down, she tells him that he is just scared, but Brian leaves moments later.
Brian returns to Doug’s sailboat in the early morning to check up on him, but he finds him in the cabin dead from suicide, having broken the cognac bottle and slashed his throat wide open with it. After getting the police and the paramedics to come and take Doug’s body away, Brian spends the next 24 hours walking through the city, brooding and thinking. Following Doug’s funeral, he returns to his apartment and finds that Kerry sent him a letter that was written by Doug, and Brian finds out that it is Doug’s suicide note. Doug tells Brian that he decided to kill himself because he felt his life was nothing but a sham, and the only thing he will really miss about it is the conversations they had.
The next morning, Brian goes back to Jordan’s parents’ penthouse and forces his way in, wanting to talk to her. He finds her and locks them both in the room they are in, and he first tells her about Doug’s suicide before saying that, despite the fact that Doug was his best friend, Doug was too proud to let him help him and too proud to show how he felt until it was too late, and he does not want to make the same mistake with her. He informs her that he has saved money and also worked out a loan with Pat in order to open his own bar, and he knows he can turn it into something great, and he tells her he loves her and wants to marry her and then begs her to come with him. Richard, his butler, and the building’s desk clerk then get into the room, and Richard tries to tell Jordan that he is only here for the money and that he is a loser, but Brian replies that he doesn’t want a thing from him. As Richard has the desk clerk try to throw Brian out, Jordan tells her father that she loves Brian and is going with him, despite him warning her that, if she goes, he is not letting her back in. When she tries to leave, Richard orders the clerk to keep her from doing so, prompting Brian to come to her defense and punch out the clerk. Brian and Jordan head into the elevator, and Richard tells the couple that they will never get so much as a dime out of him, but Brian replies that that suits him just fine.
Brian and Jordan get married and have their reception at Pat’s bar, and later, Brian opens his new bar, titled “Flanagan’s Cocktails & Dreams” (a name he had chosen back when he wanted to open a bar with Doug, based on something Doug said), and it becomes a success. One night, Brian is tending the bar with Pat and a now-visibly pregnant Jordan among the patrons, and after Brian serenades everyone with a poem about his unborn child, Jordan whispers in his ear that she is actually carrying twins. Happily surprised, Brian tells everyone that the drinks are on the house, which Pat is against (having tried to encourage Brian to never do that).