Plot

While attending his brother's wedding, a serial womanizer is haunted by the ghosts of his past girlfriends.

Connor Mead, a successful fashion photographer and a Lothario keen on casual sex, goes to his younger brother's wedding to convince him not to marry. He arrives at his dead uncle's estate during the rehearsal the night before the wedding; he starts in, taking his brother aside, trashing marriage. Later in the men's room, his uncle, who taught Connor all he knows about women, appears to him, confesses to have been wrong, and tells Connor that three ghosts will visit him that night: the ghosts of girlfriends past, present, and future. Connor has already set the breakup in motion. Can he learn anything from his life and fix what he's broken?—<jhailey@hotmail.com>

Connor Mead (Matthew McConaughey) is a flirt & a fashion photographer. He sleeps with random women & breaks up with them, with no regard for their feelings. He uses his secy Melanie for his wet work. He breaks up with his one night stands in bulk conference calls, sleeps with his models & has no respect for women what so ever.

Connor is driving to his brother's rehearsal when he passes some play swings that seem to hold significance. The groom is Paul (Breckin Meyer) & the bride, Sandra, is angry. Jenny (Jennifer Garner) is Sandra's friend. And there is only 1 blonde bridesmaids not to have slept with Connor. Connor tells Paul to ditch Sandra. Jenny overhears & threatens Conner. The minister turns out to be Sandra's dad and a sergeant from the Korean war.

Connor idolizes his uncle Wayne (Michael Douglas) who was a womanizer too. Jennifer says that she thinks Connor acts like a jerk to get into women's pants, else he is a sweetheart. Connor is jerk during the entire rehearsal & makes it clear that he is not supportive of weddings.

Connor meets uncle Wayne's ghost in the urinal who urges him not to waste his life like he did. Wanye tells Connor that he will be visited by 3 ghosts & who will force him to feel his choices & reassess his priorities so Connor doesn't end up like Wayne. Connor meets Sandra's mom & touches her boobs, thinking she is first ghost. She introduces him to the blonde bridesmaid, the only one who hasn't slept with Connor yet. In conversation, Connor lets slip to the blonde that Paul had slept with one of the bridesmaids. Sandra introduces Jenny to a single doctor named Brad.

In his room Connor begins to see Ghosts of his past Girlfriends. He finds an old high school girlfriend Allison (Emma Stone) in his room under his blankets. She takes Conner into his past to 1982 when Jenny & Connor were good friends & Jenny had a huge crush on Connor & Connor took a picture of Jenny & promised to always keep it with him. The next summer a car accident took Connor's parents life & Connor had just Wayne, Jenny & Paul left in his life. Jenny was the only one who knew Connor before he became a womanizer.

At high school prom Connor wants to dance with Jenny, but cant ask, so Jenny goes ahead & dances with school jock Pete & makes out with him. Connor is disgusted when picked up by uncle Wayne who promises to teach him about girls so that he is never hurt again in this way. Wanye takes Connor under his wings & teaches him all his tricks to pick women. He also trains Connor to become immune to a woman's feelings & not to invest emotionally in any relationship. Not caring, is power.

At 16, Connor dates Allison in front of Jenny & even makes out with her to hurt Jenny. The ghost Allison reminds Connor that he dated every girl in school except the one he loved. When Connor turns adult he woos Jenny over several weeks when she is a medical resident & in love with Pete. Eventually he manages to get Jenny into bed. But the moment he realizes he is falling for her, he remembers Wayne's advice & leaves that moment after having had sex with Jenny for the first time, hurting Jenny badly. The ghost Allison takes Connor into a room with ghosts of all women he has dated & had sex with, but never called back.

Connor wakes up & thinks it was a nightmare, at the wedding, Jenny dances with Brad & Connor grabs a drink, accidentally pushing over Sandra's cake which is destroyed. Sandra is angry. Jenny helps Connor clean up & Connor apologizes for what he did to Jenny. He wants to start over, but Jenny refuses.

Connor gets into his car & finds Melanie is there and hes happy to see her and tries to give her a hug, but it turns out that she is the Ghost of Girlfriends Present. She explains that shes the only consistent woman in his life. Melanie transports Connor into the wedding where Paul is telling everyone what a great guy Connor is & that he is, in-spite of everything, family. Melanie then takes Connor to her apartment where there are 3 women he broke up with in a conference call. Melanie tells them he's not worth it. Connor walks out and sees Wayne. Connor says he doesn't understand why all those women hate him. It starts to rain and Wayne explains that the rain is all the tears that the ladies hes slept with cried. Tissues start to fall and Wayne says those are all the tissues used to wipe away all the tears. Then Wayne says these are all the condoms you used. Connor starts screaming and running then wakes up in his car.

Connor re-enters the wedding where Sandra has found out that Paul had slept with a bridesmaid back when they were dating. Sandra destroys the wedding decorations & leaves. Paul asks Connor to leave, dejected. Connor starts screaming for the ghost of his future girlfriend. A sexy blonde appears & takes him to a Church where Jenny is getting married to Brad. Connor finds a scruffy Paul sitting in the pew, with no wedding ring. Then an old Paul is at Connor funeral, all alone. No one misses Connor. Wayne pushes Connor into his grave and all the women that hes slept with start shoveling dirt into the hole.

Connor wakes up the day of the wedding & finds that Sandra's dad is flying off with Sandra & the bridesmaids. Connor apologizes to Sandra for ruining her wedding. Connor speaks about the power of love & how Sandra should take a risk for it. Jenny realizes that Connor is simultaneously talking to her. Sandra agrees.

The wedding turns out perfect. Connor & Jenny make up after the wedding when Connor promises not to run away this time & to always wake up by her side each morning & also shows that childhood photo of hers that he had kept on his person all this while