Plot
Busking in Grand Central Terminal, Nick Vaughan sees Brooke Dalton drop her phone while running to catch a train. She misses it, so returns to the station where Nick returns her broken phone.
Nick then finds Brooke standing outside the terminal, who confesses she has just been robbed and is trapped in the city. He offers to pay for a cab to take her to Boston but his cards don't work. When Nick tries to call a friend to lend him the money his phone has died. He offers to get Brooke a room for the night, but she insists she must reach Boston by morning.
Deciding to help Brooke find her purse, Nick tracks it down at a sweatshop that deals in stolen purses. He heads inside to retrieve it while she uses a payphone to call her husband. Afterwards Brooke convinces passing police officers to investigate the building, the sweatshop owners get spooked, punch Nick, and run out with the bag.
Nick and Brooke then head for Nick's friend's wedding reception, hoping to borrow money. Along the way, they both open up about why they're in New York. Brooke had just sold a painting and was going to surprise her husband by coming home early. Nick has an audition for a band he has been dreaming of playing with.
Instead of reaching the reception, they stumble upon an event where they are mistaken for members of the band. Nick and Brooke perform "My Funny Valentine" and flee when the real band shows up. After their last-ditch attempt to get a bus to Boston fails for lack of funds, Brooke borrows a phone, calls a friend, and begs her to retrieve the letter she has left for her husband that she does not want him to read.
Elated that her problem is now solved, Brooke offers to accompany Nick to the reception and pretend to be his girlfriend in front of his ex, Hannah. There, once Nick sees Hannah and meets her new boyfriend, he leaves abruptly. Outside, he explains this was the first time he had seen Hannah since she rejected his marriage proposal and broke up with him six years ago.
At Brooke's insistence, Nick goes back to speak to Hannah and discovers that she is pregnant, so finally gets closure. Wandering around the city, the two find a psychic who is still open. After he reads her future, he allows Brooke to use his phone so she learns her friend couldn't retrieve the letter.
After leaving the psychic, Brooke reveals that she discovered that her husband was cheating on her. Though he ended the relationship, she discovered that he was going to see his mistress again. Devastated, she wrote him a letter ending their marriage and went to New York for work. However, during her trip when her husband called to say he was coming home early, she realized he must have broken ties with his mistress.
At a restaurant, Nick tells Brooke that her husband will most likely understand why she wrote him the letter. She, worried about the possible end of her marriage, sneaks out the back of the restaurant and tries to hail a cab to the airport to fly to her mother's in Indiana.
Nick appears, frustrated that Brooke tried to bail on him, and they argue. Going to Nick's friend's hotel room, they unwind from the night's adventures. They then share a kiss, write on the back of paintings in the room (a reference to an earlier encounter with a painting with erotic writing on its back) and reflect on their night.
In the morning, they return to the train station. Just before they part, Nick makes a pretend call from a phone booth. Using it as a "time machine" he calls himself in the past, saying he will meet a woman and "you will need her more than she needs you". They share one last kiss and finally part.
On her way home, Brooke finds a guest service paper they had filled out at the hotel. On the bottom it says, "Turn over". After reading what is on the back, she smiles.
