Connor Mead (Matthew McConaughey) walks into a building where his assistant, Melanie, meets him and gives him all of his messages and such. He stops behind a camera and takes one photo of a bunch of women in their underwear. He and his assistant keep walking and run into more women in their underwear, who invite him to dinner. He says he’s booked and as they walk away, he tells his assistant to book them too. He walks behind a curtain and meets a singer who is supposed to be on the cover of Vanity Fair. He strips her down and puts an apple on her head and tells a lady with a bow and arrow to shoot the apple and he takes the picture.
Connor and the singer are making out when the assistant comes in. She tells him about three messages he has from various women he’s been seeing and that he needs to leave soon to make his brother’s wedding rehearsal. He asks his assistant to break up with the women for him, but she refuses. He tells her to put them on a conference call. She puts all three on the computer and he proceeds to break up with them. The singer says that Connor is as bad as they say and that she knows he won’t do that to her. He says he broke up with those women for her. They continue to make out.
Connor is driving to his brother's rehearsal when he passes some swings that seem to hold significance. He gets to the venue where the rehearsal is taking place. He knocks on the window and the groom, Paul (Breckin Meyer), is really excited that he came. The bride, Sandra, is not as happy. Jenny (Jennifer Garner) is a bit nervous also. Sandra reveals that all but one of her bridemaids has slept with Connor. The venue turns out to be Connor and Paul’s uncle Wayne’s (Michael Douglas) karate dojo. Connor tells Paul that it’s not too late and if he changes his mind, he can take his car and leave. Paul laughs until he sees that Connor is serious. Sandra sees Connor giving Paul keys and asks Jenny why he’s giving him keys. Jenny tries to cover by saying he may be giving them a car. She goes over to the guys and confronts and threatens Connor to be supportive. Paul introduces Connor to his wife and her bridesmaids and his groomsmen. They are honored to meet Connor after hearing the stories about him. The minister turns out to be Sandra’s dad and a sergeant.
Connor goes upstairs where there are pictures of uncle Wayne with various women along the wall. He gets to his room where there are flowers and lavender scented candles everywhere. Connor picks them up and throws them in the fireplace. Jenny explains that the wedding scent is lavender. Connor says that uncle Wayne is rolling over in his grave. He explains that when he was alive, his uncle used that room for weeklong orgies. Jenny reveals that people were taking bets to see if Connor would even show up. He seems a little hurt that people would think he would miss his brother’s wedding. Jenny says she knows that Connor is not really a jerk and he only acts that way to get women to sleep with him; deep down, he’s really a sweetheart. She tells him that his secret’s safe and she won’t tell anyone that he has feelings.
At the dinner, Connor wants the drinks to keep coming and someone asks him if he’s going to photograph his brother’s wedding. He says no, he’s not a wedding photographer. Jenny says he’s not used to taking pictures of people with their clothes on. Paul and Sandra come over and Sandra starts freaking out because there are no figs in the arugula salad. Paul calms her down and everyone says that the salad is fine. Paul says that Sandra and he want Connor to make a toast at their wedding. There’s a funny scene where Sandra tries to get Connor to say no. Connor says he can’t toast a wedding and that he doesn’t believe in marriage. He says love is a myth and leaves, but not before saying that some figs in his salad would have been better.
He goes to the bathroom where he sees his uncle at the urinal. He asks Wayne what he’s doing there and Wayne says he’s here to warn Connor to not waste his life like he did. Connor is confused because Wayne had a great life and he is a legend. Wayne says Connor shouldn’t want to be like him but he’s on the path of becoming like him. He says Connor will be visited by three ghosts and will be forced to feel things he hasn’t felt in a long time. Wayne disappears and Connor is freaked out and calls Melanie and leaves her a message. He sees a woman and reaches out for her breast and says they look real and she says they are and that she likes to be bought a drink first. She turns out to be Sandra’s mom, who’s been divorced eight years and hasn’t talked to the sergeant since. He rants about how single people get a bad rap and that casual sex shouldn’t be treated like a crime. He asks if they’re off limits and she says definitely. She tells him that the bridesmaid that he hadn’t slept with has been eyeing him the whole time they were talking.
Sandra tries to hook Jenny up with a guy, Brad. Sandra makes it really awkward so Jenny and Brad leave. The bridesmaid come up to Connor and asks what he and Sandra’s mom were talking about. He says casual sex and then apologizes to her for making her feel left out because she’s the only bridesmaid he hasn’t slept with. He sends her up to his room. Brad and Jenny come over to Connor and Jenny and Connor banter.
Connor goes up to his room where he hears a woman under his blankets. He thinks it’s the bridesmaid, but it’s a lady in eighties get up and braces. He remembers her name is Allison and she gets excited. She tells him that she’s is the ghost of girlfriends past and runs out of his room. She appears in front of him outside and he runs back inside the room. She is there waiting and he says that she’s not real and she’s only a repressed memory activated by all the alcohol he’s been drinking. She says she’s going to take him to visit all his past girlfriends. They fly off and land back in time when he was young, the time of his first relationship. Young Connor is running toward the swings that Connor had passed in the beginning of the movie. Young Jenny is running behind him and Young Connor says that he beat her. She says no, she let him win because it’s his birthday. He points out that there’s a gift next to the swings and she gives it to him. It’s a Polaroid camera and he tells her she’s the best. She asks what else he thinks of her. He takes a picture of her and when it comes out, he says it doesn’t look like her because it looks like a girl. Young Connor says he’s going to keep it forever. Allison starts swooning and Connor claims he never said that. He asks if Allison edited the moment or if it’s his brother. Allison keeps rewinding the moment where young Connor says that he’ll keep it forever. Young Connor and Jenny look like they’re about to kiss when he jumps up and starts running and she calls him a cheater. An older man picks up young Connor. We find out that the man is Connor’s dad and it is the summer before the car accident. Connor’s dad and mom are walking arm in arm and kissing and Connor remarks about how happy they look. Young Connor, Jenny, and Paul are at a funeral and Allison explains that Wayne, Jenny, and Paul were all he had left after the accident. Jenny was the only person who knew him before he became a womanizer. At the funeral, young Jenny takes young Connor’s hand.
They arrive at middle school where young Connor and Jenny are there together talking about how lame the dance is. Allison explains that this was the time where they were trying to figure out if they were going to take their friendship to the next level. A slow song starts playing and young Connor and Jenny are looking at each other. Connor tells his young self to ask her to dance. Just as he’s about to, Jenny’s friends come shrieking saying a jock, Pete Hastings, wants to dance with her and probably will make out with her. She turns to look at young Connor, who’s looking down. She turns around and says OK and walks off as young Connor looks after her. Connor tries to console his young self, who can’t hear him. Allison says at least Pete didn’t choke and starts fake gagging. Connor claims he was just being a gentleman. Young Jenny and Pete start making out and young Connor runs off and gets into his uncle’s car. Wayne notices that he’s crying and starts venting about how Jenny’s first kiss was with the jock. Wayne says that he dodged a bullet because he shouldn’t want to be anybody’s first or last kiss. Connor and Allison are in the backseat listening to the whole conversation. Young Connor says he doesn’t know what to do and it sucks feeling this way and he hates girls. This prompts Wayne to stop his car and demands young Connor to stop talking like a sissy. He says he can’t teach young Connor algebra or camping or ethics but he can teach him about girls. Young Connor is excited and says he’ll do anything to never feel like this again. Wayne speeds off and takes young Connor to a bar, which he calls a “classroom.” Wayne orders two scotches and tells him the “rules.” Young Connor is looking around at all the women and Wayne says rule #1: don’t look at them. Young Connor takes a sip of scotch and spits it out. Rule #2: Don’t soil your wingman. Wayne explains that women love to laugh, especially at men because it makes them feel powerful, which in turns makes them feel comfortable, which makes them prone to errors in judgment, like having sex with strangers. Young Connor says he’s not allowed to talk to strangers. Wayne says that’s good no talking, no phone numbers, no first or last names. Allison yells for someone to call child protective services. Connor shushes her and says let the prophet speak. Wayne explains to young Connor that an ugly woman doesn’t always have a shot with a man, but a man always has a chance because cool comes from the inside. Connor is listening with a smile beside him. Wayne gives young Connor tips like give a girl two compliments above the neck, and then insult her to flip the power dynamic. Young Connor says that Jenny doesn’t like games and Wayne tells him to forget about her because his feelings for her are killing his game. Wayne says the one thing young Connor has to learn is that the power of a relationship lies with whoever cares less. He also says that one day, if Connor wakes up with a woman spooning him, he must run out of the room because sometime in the future, he’ll be crushed again. He then asks young Connor how he would approach the ice cold blonde behind him. Young Connor says he would talk to the girl next to her to make her jealous. Wayne says he never felt like Connor was his son until that moment. Wayne gets up to leave, but young Connor wants him to try to pick up the blonde. Wayne says he should throw small fish back to the sea, but young Connor wants to see his uncle in action so Wayne goes to pick up the blonde. Connor tells Allison to watch his uncle’s move. Wayne talks to the blondee’s friend and gets slapped in the face. He walks over to young Connor and says that’s how it’s done and young Connor says what’s he talking about and that he struck out. The blonde walks up behind Wayne and tells him that just because her friend’s not into whatever he said, that she’s not like her and young Connor smiles. Allison says Connor was never the same and they leave.
They’re in a basement and young Jenny’s there. Allison explains that he hadn’t seen her for two years while he was at the hand of his master. Young Connor arrives and walks down the stairs. The group of girls that Jenny’s with start talking about all the rumors they’ve heard about him like he was home schooled in Vegas for two years and he was in Bangkok. Jenny is looking at him and smiling and he sees her but he walks away to another group of people. Connor yells after himself saying nice move. Young Connor looks back at a dejected/angry Jenny and her friends are laughing telling her that he doesn’t want to talk to her. They comment that he looks like both members of Duran Duran. Young Connor starts making out with a girl and Allison is excited because it’s her younger self. Jenny walks out of the room. Allison tells Connor that they dated for 39 minutes and he didn’t get the girl he really loved, but he did get all the other girls in high school. She asks if he remembers his first time with her and that he didn’t last very long. She compares being his first to being like Neil Armstrong.
Cut to a few years later and young Connor is an adult with long hair. He is now a photographer and he’s explaining to a bunch of women how he is inspired by women. Jenny walks by and young Connor gets up to say hi. He excuses himself to buy a drink for the girl who blew him off for Pete Hastings. She says she didn’t blow him off, he choked and he admits it. She asks what he’s doing with all those women and he says that he works for a famous photographer. She says that she’s a doctor (first year resident) and he talks about how he makes $125K a year and orders drinks in Spanish. She is turned off by his actions and asks if he’s going to try to get her into bed now. He says yeah and he didn’t buy her a drink just to see how she’s been. He asks her how she’s been and she says she and Pete are madly in love and live in a house and there a lot of slow dancing in her red dress. Young Connor says it was a hot pink dress. Jenny’s friend comes to get her to leave and young Connor wants her to give him her number. She says no and he says that he has a medical condition and by law, she has to see him. She asks what his condition is and he says broken heart. She laughs and he says he wants a little dinner and sex and she says just dinner and he’s reluctant. She walks away and he says dinner’s good. She comes back to him and he wants to have dinner right now. She says OK but only if he buttons up his shirt because he looks like a gay pirate. They are walking down the sidewalk after dinner and laughing. Jenny can’t really walk straight but they reach her house. Young Connor starts making fun of himself and how he had mentioned his salary before. Connor and Allison arrive to see this and Connor says he should put the self deprecation back in his play book. Allison says she’s concerned that he may be missing the whole point of this trip down memory lane. Young Jenny tries to say good night, but young Connor tries to get into her house. She says no and that he has to woo her for his own benefit. Connor asks Allison what’s next and she says they’re going to watch a montage of young Connor and young Jenny while listening to Time After Time. There are various scenes of them playing foosball, taking pictures, going on dates, etc. After several weeks of wooing, young Jenny and young Connor go to her bedroom. They are in bed and Connor and Allison are there too. Young Connor says that the sex was amazing and young Jenny says it’s because they had 20 years of foreplay. Young Connor gets up and gets dressed and young Jenny asks what he’s doing. He says he has work early tomorrow morning and she says her alarm is set. He explains that he doesn’t stay over and she says there are two types of women ones you shag and leave and ones you shag and snuggle with. She gives him three seconds to get back in bed with her or he is to never call her again. He gets back into bed and spoons her. Allison tells Connor that this is the moment he truly fell in love with Jenny and the moment he realized he was spooning. Young Connor gets up and leaves. Young Jenny wakes up to no one next to her and Connor says he doesn’t want to watch. The phone rings and young Jenny picks up her phone and tells the person she’ll be right there then starts to cry. Allison tells Connor that was when he officially became Connor Mead. Allison pushes Connor out of the room and tells him she’ll buy him a drink.
Allison and Connor arrive at a place with all the women he’s had “relationships” with. She tells him that after Jenny, his relationships became shorter and shorter. He’s walking through a row of women who tell him where they had sex and how long they dated and that he never called them again. He asks Allison how many more there are and she says a lot. He looks down into a seemingly never ending line of women. Suddenly, all the women start grabbing at him and saying they miss him. He yells get off and then you see him in his uncle Wayne’s room wrapped in a blanket and rolls off the bed.
Downstairs, the sergeant is showing off his seating chart and Jenny sees Connor. Connor is in desperate search for alcohol and goes into the kitchen where he finds a box of wine. He pops the cork and starts drinking when he notices the wedding cake tipping over because the cork hit a part of the stand on the wedding cake. He saves the cake, but the leg is out of his reach so he has to keep holding the cake. He looks for a replacement and sees the bottle of wine and tries to get it. In the other room, Jenny is organizing the wedding dance when Brad asks her to dance. She is reluctant, but Sandra tells her to dance. She and Brad start to dance and he’s a very good dancer. She asks him where he learned to dance and he says he spent some time in Colombia; Sandra adds that it was with Doctors without Borders. Connor is still trying to get the wine, when suddenly he screams. Jenny comes rushing in and Connor is on the floor with the cake on the ground. Sandra comes in and falls on her knees. The rest of the family comes in and Connor says that the cake wasn’t very good. Sandra is upset that he had a piece and he says it just splattered in his mouth. She starts going off and her dad holds her back. Jenny tries to calm everyone down and Connor tries to sneak out.
In another room, Sandra is getting massaged to calm down. The bridesmaids start saying that Connor is ruining the wedding and Operation Sex for Every Bridesmaid. The blonde bridesmaid from before admits that she almost hooked up with Connor earlier.
Back in the kitchen Connor is on his hands and knees cleaning up the cake mess while Jenny is watching him and laughing. He apologizes for how things turned out between them. Jenny takes some of the blame because she was always attracted to men she thought she could fix, but after Connor, she vowed to only date adjusted, fully functional men. He asks how strong that vow is and kisses her. She pushes him away and he tells her that he’s changed and he sees things in a whole different way and that he thinks he loves her. She tells him to stop and that she knows him and when she wakes up tomorrow, he won’t be there. He begs her and says he doesn’t want to be alone because there are ghosts in his bedroom.
He goes up to his room where he hears a voice underneath the covers. He thinks it’s a ghost and runs out, but it was just one of the bridesmaids. He gets into his car, but it won’t start. Melanie is there and he’s happy to see her and tries to give her a hug, but it turns out that it’s the Ghost of Girlfriends Present. She explains that she’s the only consistent woman in his life. She asks if he’s ready and he braces himself. She asks what he’s doing and he says he thought they were going to fly off. She says she the ghost of the present and that they’re there already and gets out of the car.
They enter the dojo where everyone is laughing and making fun of Connor’s shallowness. Paul comes to his defense and says that he basically raised him (touching scene). Jenny walks in as one of the bridesmaids and says that Connor has Jenny so twisted that she isn’t taking advantage of Brad’s interest in her. Jenny walks out and Connor follows her into the kitchen, where she’s crying and trying to fix the cake. Brad comes in and Connor is irritated. Brad jokes that he used to be a pastry chef and asks if she wants to talk. She says that she hasn’t seen Connor in a decade and the moment she sees him, it’s just like it was before. Brad says that the doctor’s joke is that they never break up; they just go into remission, which makes Jenny laugh. He says the only way doctors get over someone is by finding someone else to love. Connor is upset because he’s bringing them together. Melanie says it’s time to go, but Connor wants to see what will happen. She slaps him and they are in a room with the three women he broke up with in a conference call. It turns out that it’s Melanie’s apartment and she tells the women that he’s not worth it because he’ll always be alone tomorrow morning.
He walks out and sees his uncle who asks how he’s holding up. Connor says he doesn’t understand why all those women hate him. It starts to rain and Wayne explains that it’s all the tears that the ladies he’s slept with cried and tissues start to fall and Wayne says those are all the tissues used to wipe away all the tears. Then he says these are all the chocolates you’ve sent them. Connor braces himself, but nothing falls and his uncle laughs and says that Connor doesn’t send chocolates. Then Wayne says these are all the condoms you used. Connor starts screaming as condoms start falling out of the sky, but he ends up lying on his car.
He walks into the dojo where Sandra is throwing the wedding decorations in the fireplace. Connor says that they won’t believe what just happened to him and they all stop. He asks if all the fuss is about the wedding cake and Jenny tells him no it’s about the fact that Paul slept with one of the bridesmaids and Sandra found out. Apparently, Paul and Sandra were going out at that time. Paul apologizes over and over and Connor says Paul clearly loves Sandra and if Connor can see that, then it must be real. Jenny asks how Sandra can trust Paul anymore and Connor asks if she’s talking about Paul or Connor. He also points out that the bridesmaid is also to blame. Sandra storms out and Paul asks Connor to leave because all he’s done is make things worse.
Connor leaves and starts yelling for the ghost of girlfriends future. He claims that this was the ghost he was most looking forward to because he wants to see all his future girlfriends. A floating figure appears and he follows her. They end up in the woods and go to a church where a wedding is taking place. Connor is shocked because he thinks he’s getting married. Jenny walks down in her wedding dress and Connor is OK with it until he sees that the groom is Brad. Connor keeps yelling no but no one can hear him. He tries to break Jenny and Brad apart by jumping on him, but he flies through them. The church is empty and he sees Paul without a wedding ring. It turns out that he didn’t get married because of Connor. Connor follows Paul outside and Paul turns into an old man. Paul is the only person at Connor’s funeral. Wayne appears and says that no one really misses him. Paul gets up to say a few words saying that Connor was a great brother. Wayne pushes Connor into his grave and all the women that he’s slept with start shoveling dirt into the hole.
Connor wakes up in his bed screaming. He’s happy to be alive and opens up the window and shouts I’m alive out the window. He asks a boy who is shoveling snow if it’s Christmas. The boy says no, it’s Saturday. Connor is excited because he hasn’t missed the wedding yet. He runs down the stairs where nothing is happening. He asks Paul if he missed the wedding and Paul says no that Connor got his wish and Sandra called off the wedding. Connor says they can’t split up because they’re meant to be together and Paul says Connor is being a sarcastic prick. Connor says he’s not being sarcastic and asks where Sandra is. Paul says that the sergeant is taking Sandra and the bridesmaids to the airport and that it’s over.
Connor runs out and takes his uncle’s car because his car is buried under snow. Connor follows the sergeant’s car and flies past them when he realizes he doesn’t know how to drive stick. He tries to brake, but it doesn’t work so he jumps out of the car and the car crashes. He runs back to the road where the sergeant and the girls see him. The sergeant brakes and gets out of the car and Connor says that he needs to talk to Sandra. The sergeant refuses and Connor punches him which knocks him out. Sandra gets out and Connor locks the bridesmaids in the car but they crack a window open. He apologizes for destroying the wedding cake, going to second base with her mother, punching her dad, and breaking up her wedding. He begs her to not run away because she and Paul have something rare and wonderful. She yells that he cheated and Connor says to get over it because it was years ago. He says that Sandra’s not mad at her friend because she doesn’t actually care because she’s so in love with Paul that she forgave him the moment she heard and that’s what scares her. Sandra says that he doesn’t know how she feels and he says he knows exactly how she feels because he was in her shoes. He says he thought what if she (Jenny) hurt him or left him or died; it would have been the end of him. He says that’s why he cut it short, but it was the biggest mistake he’s ever made and that Sandra’s making the same mistake. He tells her to risk love because if she doesn’t she’ll end up like him. He tells her that she may get hurt, but any pain she feels will never be as bad as the regret of walking away from love. Sandra says that she thinks Connor might be right and that she wants to get married. The bridesmaids cheer in the car.
Paul is packing when Sandra comes in and hugs him. Jenny is going through a check list and she calls for a photographer and Connor volunteers. At the reception, the sergeant is giving a toast by telling a story about the battlefield. Connor gets up to give his toast. He says that someone once told him that the power lies with the person who cares less, and while that may be true, power doesn’t mean happiness; happiness happens when people care more, like his brother, who gives love and doesn’t expect any in return. He says he wants to be more like Paul so that Paul can be proud of him again. He also tells Sandra that his mom and dad would have loved her.
The bridesmaids come over and tell Connor that they want to hook up with him. Outside, Jenny is on the swings and Connor sneaks up behind her. He congratulates her on pulling off a great wedding. She asks what happened last night because yesterday, he was his usual awful self, but today he became the guy she used to know. He declares his feelings for her and she says she wishes she could believe him, but she’s been through this before. He takes out his wallet and pulls out the Polaroid picture he took when he was really young. She is shocked and happy that he kept it. He asks for one more chance and he’s in for the wooing and spooning. He promises to be there every time she wakes up in the morning. They kiss and he sees his uncle in the window. The song from the dance when he was in middle school plays at the wedding and they can hear it outside. Connor asks Jenny to dance and they dance outside. Inside, Melanie arrives and catches the eyes of Brad. Wayne hits of ghost of the future and she throws a drink in her face. He hits on Allison and she says she’s sixteen and walks away, to which he says they’re ghosts so they’re ageless.
The bridesmaids scope for other guys and go for the geeky groomsmen.
Sandra’s mom and dad dance and congratulate each other on a good job raising Sandra. She calls him Mervis and one of the guests overhears. The sergeant threatens to kill him if he ever calls him that.
Sandra throws the bouquet but an arrow comes flying out of nowhere and pins the bouquet to the wall. The women turn and it’s the lady from the photo shoot with the apple.
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