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The movie starts with Anna Foster (Mandy Moore) getting ready for a date. She puts on makeup and keeps changing outfits, very excited. Then the camera pans out of her window and you see that she's in the white house. A boy drives his car to the main gate to pick up Anna for their date. The many guards who all have guns take his ID and search the car, ruining the flowers by searching them. Finally he picks up Anna and they drive out but are followed by around 4 or 5 secret service cars. The resteraunt is being monitored by all the secret service agents although they're pretending not to be there and communicating through ear devices. One of the males who's watching in the van out front through TV screens is flirting with another pretty female guard, who brushes off his attempts. Anna and her date are having a good time and he says he's amazed she can live like this after a mother comes and takes a picture of Anna with her daughters. They start talking until the boys friends come up and the guards are suspicious. Then one says he knows how to make the night more special and reaches into his jacket. All of the people of the restaurant jump on him because practically all of them are secret service agents. A few minutes later, while there are all these police and cars in front Anna apologizes to her date. The boy who got jumped on is being searched and saying it was just a camera, which was true. Anna's date says that he can't date her because of all this. He breaks up with her and she's driven back by one of her many security cars.
Anna insists on seeing her father but the guards out front his door say he's busy but she runs through them and barges in. She runs to her father and starts yelling at him, saying that everything's his fault and she'll never get to 3rd base at this rate. He raises his eyebrows and she corrects herself, saying she meant 2nd. Then she turns around and sees that around 6 important people are in the room for a meeting with Anna's father (the president). She says she should leave, and apologizes. After she's gone the president asks "What is 3rd base again?" and all the people start talking and explaining what they think it is at once. The next morning at breakfast Anna is ranting to her father and mother, saying she's sick of having so many security guards following her and not being able to be free. She says when they go to Prague the next day that she wants to have the night, after the important dinner, for herself and go to the Opera with her friend Gabrielle with only 2 guards. She makes her father promise and is very happy when he does.
They fly to Prague and play Scrabble (the President's awful, Anna's good, and the first lady is amazing) and Anna explains the schedule. She'll go to all the important state dinners and do her part as the first daughter, being a good diplomat. Then she'll get to have her night with only 2 guards at a distance. And then she'll get to go to the Love Parade with only two guards. The day before her parents had said no and so they tell her she's definitely not going. That day she spends her day doing all the things expected of her and there's a quick montage of her being the perfect presidents daughter. At the state dinner that night she's in a receiving line, politely saying hello. Her friend Gabrielle comes up and Anna and Gabrielle hug a lot. Then Gabrielle shows off her new pierced tongue, which the president thinks is very untasteful. Anna and Gabrielle talk at the dinner at the White House, still being followed by two of Anna's body guards which Gabrielle says is annoying. Anna drinks a lot of champagne.
Later they come back into the ball room and from far away the president can only recognize Gabrielle and comments that he's happy Gabrielle has found a new trashy friend, besides his daughter. It turns out that her friend is Anna, but with darker and a little shorter hair and casual but cool clothes. Anna says that they're going (to the "opera") and that she'll only have two bodyguards, and not have them swarming the place. Anna and Gabrielle leaves and the body guard asks him if he'll hold to that and he's not going to. Anna and Gabrielle walk in front of a very loud club with her two casually dressed body guards far behind them (the body guards are the ones from before, the girl who doesn't like the guy who's always hitting on her). Anna's really happy and saying that she's free and she bumps into a guy around her age (which is 18) who's taking photographs. She smiles at him and then goes into the club. The club is really large, loud, and crowded. Everyone is mashed together and Anna and Gabrielle love it. They're dancing and having a good time until Anna looks around and notices all these casually dressed people all around talking while holding they're ear to hear something... They're using the ear pieces to communicate! Thus they're her body guards the president sent. Anna is very angry and she runs into the bathroom with Gabrielle and begins to rant. Then a girl who has similar hair to Anna stumbles in, drunk or sick or something. Gabrielle says she has a plan.
Anna faints in the hallways in the club in front of her allowed two guards who are shocked and pull her up to see it's not Anna, just a girl in Anna's clothing. Then you see Anna running out of the club wearing the other's girls clothes. Guards are chasing her and there are cars in front, her guard's cars. She sees the guy from before, the guy with a camera. He's on his moped so she runs to him and asks if he can give her a ride, very quickly. He says yes and while they're on the moped he reveals his name is Ben. They loose the cars following them and then stop and she reluctantly starts to leave until he asks if she knows where she's going. She says no but that she's meeting her friend at a bar. He calls and finds the location of the bar and learns it and then rides her there.
Next they're in the bar and Anna's very drunk, drinking a huge beer while he's not drinking anything. She's talking to him about how she wants to be free and not be stuck all the time. Then suddenly the security cars pull out front and she says she has to run really quickly. And wants she gets up she says that actually she really has to pee. So he tells her to hide in the bathrooms and she says he's very smart (she's really drunk, because drinking's legal at 18 in Europe). Then he walks out front and tells the guards that she's in the bathroom and very drunk, so she'll be easy to take. He's a secret service agent, a very young one. The president learns what happened and that Anna doesn't know he's a secret service man. He quickly goes over the history of Ben (father was a secret service man killed 7 years before in the line of duty, he's a great service man, he's the youngest in Europe) and decides that they should let Anna have her freedom by not following her but have this guard with her always without her knowing. The president calls Ben on his cell phone and tells him his new job is to be with Anna at all times, with the two other guards following at all times without Anna knowing. He also tells the other secret service people that they're off the job in another call.
Cut to Anna coming out of the door of the bar with Ben. She wonders why the service people left and is happy they're gone. She and Ben walk around, secretly followed by the two guards (who're still having a subplot about the guy liking her but her not liking him, through small banter). They go to this river and look at a boat crossing which Anna says is beautiful. Anna takes off her jacket and tosses him her stuff. He asks what she's doing and she says she's undressing so she can swim. He tells her not to and is about to drag her away until she takes off her top so he turns the other way and not facing her tells her to stop and leave. She takes of her underwear and runs into the river, laughing and screaming. People at a resteraunt with a view of this watch and one takes some photos. The two guards, who're watching from the resteraunt, go up to him and take away the film. Back to Anna and Ben, Ben ran into the water clothed and tries to get her out.
Awhile later they're walking down the streets and he's very wet and complaining, she tells him that it's his fault for swimming with his clothes on. They go to this outdoor square where everyone is watching a huge screen with an outdoor opera movie playing. They begin to watch but Anna says she wants to watch up on this high rooftop (around 4 stories). Next you see them climbing and he's trying to make sure she's safe because she keeps sliding around the rooftops while talking about how she wants to do dangerous things like this. Then they watch over the banister on the roof the film and talk a little. Then sitting down she falls asleep and her head rests on her shoulder so he covers her with his jacket. It's probably very late. Then you cut to the two guards who're far away on another roof and were watching from binoculars. The girl is sitting and writing in a tiny notebook and the guy falls asleep and his head falls on her shoulder. She looks at it and rolls her eyes and then she looks away.
The scene returns in the early morning and the girl guard has fallen asleep in the lap of the guy guard, who looks very happy and pleased. She wakes up and quickly gets up and scoots away. Anna and Ben are on the roof still and she's lying down asleep and he's standing on his cell telling the president they're OK. Next you see the president who's not worried right now and saying that he had a good idea. Anna calls from a train station saying that she's OK and that it was his fault because he added all those guards in the club. She still thinks that she's been out all night without any guards even though secretly Ben is one and the other two guards have been watching. The president says he's not that mad and so she thinks that she's really free now. Then the president is given the photos from the guy's camera that the two guards took. They see that Anna's swimming in the river naked and he gets mad and starts yelling at Anna that she needs to come back right now and not go on a call. She's very upset that he traced the call and hangs up on him.
Anna starts running around the train station to get on a train so she can go to the Love Parade. Ben follows her and she says he doesn't have to, not knowing he secretly has to. Although he tries to stop her she jumps on the train so he does as well. The guards jump on another green train that's going to the Love Parade in Berlin, but Anna and Ben have accidentally jumped on the wrong green train going to Venice, which isn't near the Love Parade. The trains go in opposite directions at the same time. Ben and Anna talk in their train compartment. Anna gets mad at Ben when he tells her that he doesn't think she can take care of herself, and that the reason he followed her wasn't because he had a thing for her (which she accuses him of). Anna stops speaking to him and says she'll go out on her own after they get to Berlin. Anna falls asleep and when she wakes up she sees a weird and awkward hippie type guy in her face. He greets her loudly and they talk for a bit. He gives her and Ben each a handfull of these stickers that he says you put around wherever you go and just forget about it. Then later in life you might see one somewhere and you'll be reminded of when you put those in places and feel happy (kinda important later). Anna thinks it's great and Ben just rolls his eyes. The guy is very weird and all and he's going to the Love Train also. They get off the train and realize they're in Venice.
Anna and Ben and McGruff (the weird hippie guy) go around Venice. They're all friends, although Ben is separated from the group and not really having fun. He calls the president while Anna and McGruff go off for a second. Ben tells the president they're in Venice and then looks around while on the phone, and the president wants to know where exactly. Ben doesn't see Anna anywhere so he gets worried and runs off without saying anything. The president tells the two guards to go to Venice and look for her. They fly in a helicopter there. Meanwhile, Ben is frantically looking for Anna who was left with McGruff. Then he sees them come out of a hat shop wearing odd hats and tells Anna he almost had a heart attack. There's a montage type of thing that shows Anna and McGruff shopping with Ben in different places and the two guards looking around Venice for Anna. That night Anna and Ben want to eat at this outdoor resteraunt but McGruff wants gelato so he says that he'll go and grab some and come back. He wants a group hug so Anna hugs him but Ben won't, soon he gives in and they hug (although Ben isn't happy).
A few hours later it's dark and Anna and Ben are sitting at the resteraunt waiting for McGruff, all finished with their food. They think he's just left them to go wander and all so Anna opens her purse to pay. She notices that everything in it is gone and all there are are those stickers that McGruff had. The same with Ben's bag. They realize McGruff pickpocketed them and they need to pay the resteraunt. Also, Anna sees that her two guards are in a boat in the waters of Venice and just saw her. Even more so, the people at the resteraunt have recognized her. She starts running away and Ben follows her. They run around avoiding the guards and resteraunt people, who're chasing them. They hide under this bridge in the canal where a gondola and it's boat master, Eugenio, is. They ask for a ride and he's very excited because he's never had anyone get a ride from him before. But they say they can't pay and so he tells them no ride. They weave a story about being newlyweds who's parents didn't want them to marry and they're living on only love right now, so he gives them the ride.

They're trying to avoid the people, and Anna still doesn't know Ben knows who she is and thinks he only knows her to be some random girl that he's following around. Anna asks Ben to tell her about him. He says that he lived with his mother because his father left (before he died, but he doesn't say that) because he couldn't make the "Big Gesture" and pick the family over the job. During the ride they're going under a bridge where the waiters are standing so Ben tries to hide Anna by kissing her really deeply and they make out for a minute, so the waiters don't see Anna but Anna doesn't know he was just hiding her. Meanwhile, the two guards are together and while they were on the other train to Berlin previously the girl had insulted him and told him no one really liked him. Then that day he started ignoring her and was hurt. So she tells him that he would be good looking if he'd stop trying to pretend he wasn't balding in the front and shave that hair down a little, because she thought that was hot.
At the end of their gondola ride Eugenio says he will drop them off at their hotel but they say they don't have one so he says that they can stay with him (at his mother's house). The mother is upset with him, saying that first he stops being a good accountant for this and now he brings home his customers, until he tells her that they're newlyweds. She gets very excited. A little later Anna walks into the room she and Ben are sharing wearing only a towel. He says he'll sleep on the floor and she tells him that he can share the bed with her, thinking about the making out earlier. He says he likes the floor better and only takes off his shirt, sleeping on the ground with his jeans on. Anna gets off the bed and lies down next to him. He jumps up and turns to the wall and says no, that he won't do that. She takes off the towel and he turns around to repeat what he was saying and notices she's naked. He holds up a blanket so it covers her and tells her that she has to sleep on the bed and he'll sleep on the floor. She's very upset because she thought her loved her and she loved him. He waits until he's heard her get under the covers and then sleeps on the ground.
In the morning they're leaving when the mother tells them she hopes they're happy but that she didn't hear anything last night and the walls are paper thin. Anna tells her that he doesn't think she's beautiful and the mother tells him to tell her that she's beautiful, so he does, and kiss her. Anna flounces away before he can. Anna thanks the mother very much for letting them stay. Eugenio drives them to the border of Berlin and drops them off, Anna gives him the stickers as payment and he recognizes them and is happy. They begin to walk but Anna won't talk to Ben, because she's still mad at him. A truck comes by and Anna jumps in the back with two burly type men and waves goodbye to Ben who begins running after it. The truck drives away. Ben keeps running and takes a kids bike, giving him the stickers. Meanwhile, Anna was dropped off by the truck and was wished luck. She keeps walking and comes across a large bridge that's hundreds and hundreds of feet high. A bunch of hippie Love Parade type people are there and a guy is outside the railings and about to jump. Anna screams for him not to jump but he does and she notices he's attached to some sort of bungees. He flies all the way to the bottom and dunks straight into the water before he bounces up again and again. Anna notices someone else is about to jump. McGruff! She goes over and tells him off for stealing her things but he says it's for love.
Ben comes there are his bike just as Anna's getting harnessed in. Ben says not to. Then it cuts to them hooked up together to the bungees outside the railing. Anna's very scared and says that doing the things you're scared of is generally more worthwhile when Ben asks her why she's doing this. They jump, and because they're hooked together they're basically hugging tightly the entire time. They're almost made up. Meanwhile the two guards are questioning the mother of Eugenio about two people. She's showed the pictures and recognizes them saying "Oh! The newlyweds!" The guards think that Anna's married now and the president is told she might be and is very worried. Then, that night Anna and Ben are camping out with the other hippie types they jumped with. McGruff is there also, hiding on a tree branch over a pond or something. Ben tells him he'd better stay there and then McGruff reaches out to catch something that Ben threw and falls into the water (comedy moment). Anna's still kind of mad at Ben because he wouldn't do it with her.
Gus Gus, a random hippie guy who's huge, comes up and asks Anna if she wants to go with him into his tent, very suggestively. Anna says no and Ben asks why she's not since she wants to have such a wild adventure. Anna decides she will but Ben chases her saying not to. She asks him why and Ben won't give a straight answer. Finally he says because he loves her and would be very jealous. They begin to kiss and make out a lot when his cell phone rings and she says he fixed it (it was broken) and he says yes and throws it on the grass a few feet away. They keep kissing and the camera fades away as they start to do more. In the morning Ben is looking for his ringing phone in his boxers and he calls and says that they're going to the Love Parade and that he'll return Anna at this certain spot. Anna wakes up (naked under a quilt) and asks who he's talking to and Ben says some friends who're wondering where he is, and why he's not in Prague. Then he throws the cell phone in the remains of the fire. Meanwhile, the two guards are in Venice and here where they are. The guy takes off his hat and his hair is cut shorter like she suggested and she says he looks sexy. He kisses her and they  start making out. They're together.
At the Love Parade Anna and Ben and McGruff are walking around. It's a huge parade, practically millions are there. It's very loud with music blasting from a car in the center of it with large screens and things. The tons of people are dressed up weird and dancing and things in a tight pack, some on platforms that are moving as well. Anna meets Gabrielle there and is talking with her when Ben goes to make a phone call at this pay phone. The secret service agents want him to take Anna right now and make her go home but he says he'll give them Anna in an hour at that one location and they're pissed at him. He hangs up and turns around and Anna's standing right there. She thinks he's trying to kidnap her or something and runs away. He chases her and explains he's an agent and all of that. She runs away again and he disappears, because she's hard to find. She falls down in the crowd because she's tired and hot and near fainting, it looks like. She gets on the outskirts and is leaning against a tree tiredly when someone throws a beer bottle that shatters against the tree. She yells at them and they recognize her as Anna Foster, the US President's daughter.
A mob forms around her and they're pushing her around crowding her and the guys are all hitting on her badly. One guy begins to lead her away and she thinks he's helping until she learns he's just trying to get her too. Suddenly Ben comes and punches out the guys and picks up Anna who looks like she's going to faint. A large helicopter lands in the middle of the crowd and Anna is guided in it. Ben stays where he is and then walks through the huge crowds of the Love Parade and away. On a plane with her parents Anna's asleep but then looks wistfully up thinking. A small montage of moments with Ben follows.
A little while later, evidently, Anna is packing up her things to go to college. She packs a mask she and McGruff bought when they were with Ben in Venice. She looks sadly at it and her mother asks how her heart feels, Anna says it's a little broken. They hug. Next you see Anna at college at Harvard. Her two bodyguards are together, holding hands and looking at each other, with her and she says that they're in love, which is true. They walk out the gates and a pole where all these papers are posted also has a sticker, like from before. Anna smiles and remembers. Then she's coming home for a break at the White House and goes to see her dad. They talk a little about how she's changed and while she's leaving he tells her that Ben has quit the profession and is in London doing what he wanted to. Earlier in the conversation he'd suggested she do a semester in Oxford, England. It looks like he wants her to go with Ben.
It cuts to an opera theatre where Ben is taking photographs of it as a photographer. Anna walks in and everyone starts whispering it's the first daughter of the US. Someone whispers it to Ben and he stands up to talk to her. He asks why she came and she said she was making the "Big Gesture." They kiss and it pans back to two bodyguards. One of them is the guy who got together with the girl and the other is a strict body guard. The guy bodyguard from before smiles and the other just stands there sternly. The camera pans over the scenery of London and the movie's over.


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