The movie starts out with Holly (Hilary Swank) running across the streets of New York. What seems to be her being followed by a stranger, it is actually her husband Jerry (Gerard Butler). He tries to talk to her, but she doesn’t speak to him until they are in their apartment. They begin to argue about him telling Holly’s mom that they’re not going to have children yet. They fuss about how she hates her job and that she “plans” on moving out of that apartment. Jerry storms out and Holly slams the bathroom door. She slowly exits the bathroom and stands in the living room while Jerry opens the door and asks to come back in. He apologizes for saying the wrong thing to her mother and they reminisce about how they use to have nasty sex. He does a Chippendale style dance wearing only his boxers, suspenders, and a leather jacket while she watches in bed. Jerry pulls of his suspenders and one the clip hits him in the eye. She tells him to turn off the lights since he was the last one up, but refuses to because he hurt his eye.
We see a family gathering inside Holly mom’s bar. Her mother (Kathy Bates), Denise (Lisa Kudrow), Jerry’s best friend, and Holly’s sister and Sharon (Gina Gershon) plus few others are there with a priest. They are having a small funeral for Jerry, (his body was cremated). Jerry had designed his own wooden box. Everyone begins to take a shot of liquor and then places the shot glass on top of the box. We see Denise hitting on guys asking their name, if they’re single, sexual orientation, and their occupation. Daniel the bartender (Harry Connick Jr.) talks to Holly and her sister. He asked how Jerry died, and she said it was a brain tumor. It is clear that Daniel likes Holly, but isn’t suave towards her. Holly goes home with the box and places in on top of the chest at the foot of their bed. She begins to undress to go to sleep. She tells Jerry to turn off lights and she get out of bed and walks to the living room. We see a vision of him seated and playing the guitar. She tells him she can’t sleep but lays on the couch and the camera pans out and we see candles lit on top of the box.
Holly hasn’t been to work nor has she answered anyone’s phone calls. Her apartment has become a landfill with unwashed dishes, chip bags, and empty pizza boxes. Her mother, two sisters, one sister’s husband (Jerry’s best friend), and Denise enter her apartment while she was in the middle of singing along to Judy Garland. Her mother begins to somewhat clean while another sister starts to comfort her. Someone is at the door to deliver a package. Holly opens the box and it’s a birthday cake from Jerry. He also left her a letter, but she thinks Jerry’s best friend is up to it. It turns out; he has written letters for her to keep her hopes up. In the letter, Jerry tells Holly that it’s her birthday and she needs to get crazy with the girls, even with their mom. They end up at Holly mom’s bar and we see Holly in a storage closet completely wasted and crying over Jerry. Daniel enters but leaves because he can’t tell Holly why God has taken Jerry. He decides to enter and they talk about how he lost his girlfriend to a lesbian. Every girl he dates, they turn out to be lesbians. Holly throw’s up and Daniel carries her to a room upstairs in bar. The mother tells Daniel that he can go back to tending the bar, while she tucks Holly in bed.
The next morning Holly gets a call from her sister and reminds her about getting another letter. She rushes to her mailbox and there is a letter telling her to find a nice outfit because she will be going to sing karaoke. She hated to sing karaoke because in the flash back, Jerry does a song and asks for someone else to come up. Someone suggests Holly but Jerry said she wouldn’t do it, not even for $100. Holly hesitates, finishes her drink, stands up and says she’ll do it for $200. She gets on stage and beings to sing. Towards the end of the song, she trips over some power cords and ends up in the hospital with a broken nose and sprained foot. Back to the present, Holly does a song, and in the end starts to cry. Daniel is in the crowd staring at her, wishing the song was about him.
The following the day, Holly comes home with clothes from the dry cleaner. Some how along with her clothes, was Jerry’s leather jacket with a letter in the pocket. The letter instructed her to clean up all his stuff, since she could use the extra space, and send it back home to Ireland. Holly has all of Jerry’s stuff packed and Daniel comes over to help her mail them.
We see Holly waiting at her mailbox while the mailman begins to sort out the mail. Nervous and pressured by Holly’s presence, he quickly gives Holly her mail. She gets a letter and it tells her to go with Jerry’s best friend to a travel agency looking for a specific lady. The lady tells Holly he was there and grabs a box of tissue. It turns out; Jerry had planned a trip for her, a sister, and Denise to travel to Ireland. The three of them end up traveling to Ireland and arrive at a vacation home. Everyone has a letter except Holly. Later that night, they go to a pub and they see a man that resembles Jerry. Holly’s sister and Denise force Holly talk to him. They exchange names, he’s William, and she tells him he’s beautiful. He is playing live music and asks for Holly to stay and meet him up after he’s done. She agrees and stays. William dedicates an English song to her and when he starts to sing, a flash back occurs. It was the same song Jerry had sang to her in a pub while she was in Ireland as a college student. She leaves crying and William is confused on stage.
The following day, the three girls go fishing out on a boat. Holly’s rod catches a fish, but she doesn’t know how to reel it in. Her sister tries to help but they end up losing Denise’s makeup bag and the oars. They are stranded out in the lake, Denise reveals she’s getting married on New Year’s Eve and Holly’s sister is pregnant. They are rescued near night fall by none other than William and his dad. William is invited over for dinner and is suggested to stay over night by the sister and Denise. After he showers, Holly offers him a drink. She makes a move on him, but it is awkward. She said she is trouble and has issues. William says he likes trouble and they end up sleeping together. Holly asks William if he can give her a ride to another city in the morning. He agrees and asks who she’s going to see. She said she will be visiting the Kennedy’s. William knows the Kennedy and even Jerry. They have been friends since childhood and were band mates.
Holly arrives at the Kennedy’s and talks to the Jerry’s mom and dad. They asked for her to visit more often. They hand her a letter from Jerry which tells her about his fort. It’s actually a stone wall that he would sit at and do all of his writing. In the letter, it described how they had met each other and how he fell in love the moment he saw her. She was a college student on a trip traveling through European countries and was lost. Jerry had walked with her back to the town she was staying in. He had let her wear the jacket, which he had won from a bet. They ended up holding each other in order to avoid a dog he claimed was an Irish killing dog. They kissed but she quickly left. They didn’t exchange names but only that he was playing at a pub, that she didn’t want to know and she would wear his jacket.
Back in New York, Holly has found her plan. It is to design shoes. We later see her having lunch with Daniel. They haven’t ordered yet but she is constantly talking about Jerry. Daniel makes a remark and she calls him Jerry and tells him to stop. He is frustrated and says that he likes her but can't compete with an invisible man. He storms out and the waitress asks if he would be returning. Holly later ends up leaving.
The mom, sitting in her bar sees Holly running. Holly cries to her mom about how alone she is and she is hurting that both her dad (left for another woman) and Jerry are gone. The mom asks Holly to go for a walk. Holly is then presented with the last letter. The mother was in on this plan all this time and was promised by Jerry to keep it a secret. The mother was very impressed about how well everything was planned out and executed. The hard part was getting the jacket out from the apartment. She reads the letter and ends up at home rereading it.
She gets a message from Daniel about how he shouldn’t have said and acted the way he did earlier that day. Holly and Daniel end up at Yankee Stadium alone and she presents him with Jerry’s last letter. He reads it aloud and it explains how she had changed him as a man. From the time he met her until his last days, he will always love her. But for her time on Earth, there will be many more chapters for her and that she could and should move on. Daniel and Holly give each other a kiss, but it doesn’t turn out well. He sees her like a sister and vice versa. They end up staying good friends.
In the end Holly starts off saying, “Dear Jerry” and beings to narrate a letter she is writing to Jerry. Holly and her mother have taken a trip to Ireland to see Jerry’s parents. Along the way, they bump into William and his dad. The mother drops the box of custards and William's dad makes a joke. Holly’s mom laughs, which is resemblance of when her husband use to make her laugh. Williams ask if he’ll see her around and she replies yes.
The movie ends with Holly saying/writing, “P.S. Guess what?”
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