The movie opens with views of Manhattan. We eventually end up in an apartment that shows a wedding invitation on the bed. In the background is a phone message asking that Kat, played by Messing, try and forget about her failed attempt to become a bride and show up at her sister's wedding. Flash to Kat in the bathroom brushing her teeth and another message plays, this is from Nick, played by Mulroney. He is the escort she hired to act as her loving boyfriend. He tells her that he will be running a bit late and has sent a messenger to her apartment to pick up his ticket. He will meet her there. At that moment, there's a knock at the door, the messenger has arrived to retrieve the plane ticket. As Kat is handing him the ticket she is explaining to him, nervously, how she has hired a male escort to go with her to London to play her boyfriend. The messenger is none to amused and attempts to take the ticket. Kat has a strong grip on it, however, and as he explains that she will need to let go, she asks that he help her. He gently grabs her hand to remove the ticket and then hurries off to make the delivery.
Kat, realizing the time, begins to scurry around getting dressed. She grabs her passport and takes a moment to glance over some old photos of her ex-fiance. From this point on, we see a montage of Kat and Nick, both from the waste down, readying themselves and leaving for the airport.
Once at the airport we see Kat trying to get to the ticket counter, looping through the maze that leads to the ticket counter. All the while a guy is badgering her about the random crisis that are taking place at that moment and is begging her to help him. She grudgingly caves in to his desperation and asks that the counter lady check her bags. It is here that we find out that Kat is a ticket agent and apparently she has a comped ticket to London.
Once on the plane, Kat's nervousness continues. She has yet to see Nick and, to this point, has not even spoken to him. She is in the flight attendant's prep area explaining how nervous she is about how her date will look because she wants him to look his best when she is trying to make her ex jealous. At that moment the flight attendant sees him walk in and sit in the seat that Kat has stated he would be in. The flight attendant is impressed. Kat turns and looks to find Nick, a stunningly gorgeous man with a very nice suit on.
She goes over to meet him and they exchange a few pleasantries. He assures her that everything will be fine and her family will never know that they are not in love.
Once they arrive in London, Kat goes through a series of outfits, trying to find the sexiest one. She goes through so many that the bus boy at the restaurant she is changing in also begins to rate the outfits. Nick is sitting patiently through this whole ordeal and eventually tells Kat that they need to get moving as the party has already begun.
Once they arrive at the wedding gathering, Kat immediately runs into her aunt. Noticing Nick, the aunt asks who he is and what he does for a living. Realizing that they have not worked out a story yet, Kat excuses herself and Nick from her aunt's presence and dives into the coat room where she gives him his money ($6,000) and tells him that he is a therapist. Nick says nothing. She asks that he count the money. He tells her he trusts her but she insists. He counts and she apologizes for the state she is in. He tells her that if she just considers the situation for what it is, a business transaction, she will not feel a need to apologize. Furthermore, he will cover his own expenses but any physical intimacy will require a heads-up prior to the act so that a rate can be set. Kat tells Nick not to worry about that because she won't be needing him for that purpose; she explains that she finds paying for sex rather disgusting.
Back at the party, Kat runs into her mother, who is very unforgiving about the wedding that wasn't 2-years ago. So much so that during a toast to the actual bride-to-be she embarrasses Kat by bringing it up. Everyone in the room is uncomfortable with the direction the speech is heading in and it is at that moment that Kat's ex-fiance, Jeffrey, breaks the tension by playing the piano. At which point her mother gets back on track and the party continues.
Everyone at the party is very impressed with Nick, both men and women, and Kat notices this. She excuses herself to go to the ladies room and runs into her ex. He is telling her how great she looks and attempts to tell her something, but they are suddenly interrupted by Kat's very forthright cousin who wisks her back downstairs to the festivities. Kat is thanking her for the reprieve when the cousin notices Nick and wonders who the gorgeous specimen is. Kat explains that it's her new beau and she is both jealous and happy at the same time.
Sometime during the course of the party Nick runs into Kat's ex, Jeffrey, and they talk about how Jeffrey is heartsick over a woman who is at the party with another man. He feels that he was silly to have let her go and wants desparately to have her back again. Just then Kat swoops in and kisses Nick. Jeffrey solemnly walks off with his tail between his legs.
After the party, Nick and Kat are back at her parent's home where they will be sharing a room. Nick begins undressing as Kat tries hard not to watch. He explains that it is okay because it's "part of the package". Nevertheless, she continues to try and keep her eyes down. As Nick walks to the shower she turns and gets a small glimpse of his bare bottom, she blushes, and goes back to unpacking. As he showers, she decides to ask him a question regarding a quote he made in a story about every woman having the exact relationship she wants. He is a little surprised that she knows the author of the article is him, especially since it was supposed to be an anonymous story. Kat explains that she has a friend at the magazine and she asked who he was. He is a bit perturbed by this obvious lack of privacy but answers Kat's question anyhow. She asks if he is implying she wants to be miserable and pine away for a man she may never have. He said she does indeed and when she's ready she will let go of him and move on.
Kat is at a bachelorette party now getting all liquored up. As she is leaving the party she stops at the ATM and withdraws a good bit of cash. Once she gets back to the house, Nick is asleep. She wakes him up and leads him to the sail boat outside where they make love for the first time. When morning approaches it is obvious that it was more than sex for both of them, but neither will admit it. Nick confronts Kat about the money she left on the bed for him and she is befuddled because she wasn't sure if anything could or would happen. He is upset by the whole scene and storms out of the room letting her know that she is a bit short for what happened.
Now, we are at a dance class. Nick and Kat are still seething but find themselves lightening up as the music plays on. By the time the scene ends they are laughing in each other's arms.
The day before the wedding is spent at the groom's, Eddie's, home. Kat and Nick are both in good spirits. They are sitting around with Kat's stepfather talking when Nick volunteers to go find Kat's sister; her fiance is frantically searching for her so he can serve her lunch first. No one has seen her. Nick looks for her in the boathouse and manages to walk in on a heated verbal exchange between she and Jeffrey. Jeffrey quickly tries to cover up the incident and walks out. Nick listens to the explanation which is vague, but implies that there is more between Jeffrey and Kat's sister than has been let on before now.
During dinner, Kat and Nick are acting like a true couple. Kat excuses herself to get more wine. Shortly after she leaves, Jeffrey goes behind her. Nick, feeling that Jeffrey is about to tell Kat something massive, follows as well. While in the cellar with Kat, Jeffrey is trying to muster up the courage to tell her something. Nick stops shy of making his presence known and merely hears Kat say that whatever it is doesn't matter because she is over their relationship now and simply wants to move on. Nick walks away smiling upon hearing this from Kat. As Kat turns to leave, Jeffrey confesses that he slept with her sister the night before their wedding and that was the reason he called it off. He went on to say that he continued sleeping with her until his best friend, Edward, proposed. Kat is devastated.
She walks back into the party looking like a ghost. Her cousin, the same one who saved her from Jeffrey early on, admonishes Jeffrey for telling her. Kat is surprised to know that this is not news to anyone but her. She runs to Nick and as he holds her, her sister directs anger his way thinking he is the one that spilled the beans. Kat removes herself from Nick and runs off. Nick chases her and they have a brief conversation about how she thought they had a chance for more and he tries to explain why he kept the information from her. She is too angry to listen and he storms off stating that now she can use their interaction as a reason for not trusting anyone.
Later on, Kat's sister walks into the room and asks that Kat not tell Edward because she wants to tell him herself. Kat is bitter and angry and lets her know that he won't hear it from her, but as of now she wants nothing to do with her.
Nick leaves to spend the night in the boathouse and tries to find a flight out as early as possible. Meanwhile, Kat lay in bed hurt and confused.
The next morning the wedding festivities begin as bridesmaids and flower girls scurry towards the chapel. Once there, Kat goes off on her own. Her father finds her and speaks to her about Nick. He tells her that if she wants him, she should go after him. She agrees and runs off to find him. At the same time, Kat's sister is confessing to Edward what happened between she and Jeffrey. He tells her that he always knew there was someone, but he never knew who. It hurt more to know it was his best friend. He storms out in a rage and chases after Jeffrey.
Flash to Nick who is speeding off, presumably toward the airport, before having a change of heart. He heads instead to the church where he sees the enduing chase between Edward and Jeffrey. Nick advises Edward to stop chasing him because he is long gone. They both sit in the car and talk. In the meanwhile, Kat arrives at the boathouse to find that Nick is not there; furthermore, he has left the money.
Back to Edward and Nick. Nick tells Edward that if after knowing all the he knows, he would still rather be with that woman more than anyone else, he should follow his heart. Plus, make-up sex is the best kind.
They rush back to the chapel. Edward runs inside to marry his bride. Nick sees Kat and they decide to give it a go. Nick ends up the best man at the wedding.
In closing, we see the couples dancing merrily with one another. We learn that Nick and Kat started dating. Edward and his new bride discovered the best make-up sex ever and Jeffrey never learned a thing; by story's end he was already in the hunt for new prey to conquer.
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