From "High Fidelity", Rob break ups with his current live-in girlfriend Laura and then tries to rationalize the whole thing (and his behavior), but comparing her to his ex-girlfriends going back to middle school. But as he revisits each of these relationships, he realizes not of these girlfriends can hold a candle to Laura. Just some great passive-aggressive behavior exhibited by Rob to minimize the relationship and the pain he now feels. Rob: My desert island, all-time, top-five most memorable breakups, in chronological order, are as follows: Alison Ashmore; Penny Hardwick; Jackie Alden; Charlie Nicholson; and Sarah Kendrew. Those were the ones that really hurt. Can you see your name on that list, Laura? Maybe you'd sneak into the top ten. But there's just no room for you in the top five, sorry. Those places are reserved for the kind of humiliation and heartbreak you're just not capable of delivering. http://www.youtube.com/watch?v=pneBeIJquJA

From "Bull Durham." Nuke (Ebby Calvin LaLoosh) and Crash go back to Annie's apartment, where she will let them know who she will spend the season with. Crash gets fed up with the whole process and delivers one of the great monologues in recent movie history. He breaks up with her even before they get together... because he doesn't feel it's fair he has to compete against an undeveloped man-boy. Ebby Calvin LaLoosh: So is somebody going to go to bed with somebody or what? Annie Savoy: Honey, you are a regular nuclear meltdown. You better cool off. Ha ha, ha ha! [to Crash as he stands up] Annie Savoy: Oh, where are you going? Crash Davis: After 12 years in the minor leagues, I don't try out. Besides, uh, I don't believe in quantum physics when it comes to matters of the heart. Annie Savoy: What do you believe in, then? Crash Davis: Well, I believe in the soul, the cock, the pussy, the small of a woman's back, the hanging curve ball, high fiber, good scotch, that the novels of Susan Sontag are self-indulgent, overrated crap. I believe Lee Harvey Oswald acted alone. I believe there ought to be a constitutional amendment outlawing Astroturf and the designated hitter. I believe in the sweet spot, soft-core pornography, opening your presents Christmas morning rather than Christmas Eve and I believe in long, slow, deep, soft, wet kisses that last three days. [pauses then winks and walks away] Crash Davis: Goodnight. Annie Savoy: Oh my. Crash... Ebby Calvin LaLoosh: Hey, Annie, what's all this molecule stuff? http://www.youtube.com/watch?v=sBfdl6hNZ9k

The Perks of Being a Wallflower - primarily because it is the screenplay I am currently reading, but also because I thought this was a great film. Charlie's major indiscretion during a game of truth or dare is a great scene that is both funny, and devastating....and a good reason for never playing truth or dare. It's a break up that we, as the viewer expect, but no one in the scene (possibly not even Charlie) expects. INT. CRAIG'S LOFT APARTMENT - NIGHT Truth or dare. The gang is seated in a circle, drinking from plastic cups. Charlie sits between Mary Elizabeth and Sam. BOB PATRICK Who are you talking to? BOB I dare you to kiss Alice. PATRICK (licks his lips) Get ready, breeder. As Patrick approaches an apprehensive Alice... CRAIG Mary Elizabeth? Samantha told me that you got into Harvard. Congratulations. MARY ELIZABETH Thank you. (re: Charlie) This one still hasn't gotten me flowers. (to Charlie) But I forgive you. She kisses him. Charlie bites his cheeks. Sam looks a little depressed. CRAIG (to Sam) Don't worry about Penn State. You're just wait-listed. PATRICK Excuse me, everyone, but you're missing some hot "fag on goth" action. Anticipation. Patrick is getting ready to plant the biggest kiss on Alice when she jumps him. Everyone groans. Ew! Laughter. Patrick looks for the next person. Charlie's heart pounds. Don't pick me! Please! PATRICK (CONT'D) Okay. My turn. Um... let's think... Charlie... truth or dare? Silence. Thinking. Finally... CHARLIE Truth. PATRICK How is your first relationship going? CHARLIE It's so bad that I keep fantasizing that one of us is dying of cancer, so I don't have to break up with her. PATRICK Charlie? Truth or dare? Charlie blinks. It was all fantasy. CHARLIE Dare. PATRICK I dare you to kiss the prettiest girl in the room on the lips. Notice I charitably said girl and not person because let's face it... I'd smoke all you bitches. Alice hits him. Laughter. Charlie thinks. He looks at Mary Elizabeth, then turns to Sam. Before Sam can even react... Charlie plants a kiss right on her lips. When he opens his eyes, he looks around, and realizes the magnitude of his mistake. Everyone stares. After a horrible silence... PATRICK (CONT'D) Now that's fucked up. Without a word, Mary Elizabeth just stands, dignified, and goes into the kitchen. CHARLIE Mary Elizabeth, I'm sorry. I'm-- Alice follows Mary Elizabeth. Sam is close behind. CHARLIE (CONT'D) Sam?! Sam! I'm sorry. I didn't mean anything by it. I'm sorry. Sam turns and looks at him. She doesn't even recognize him. SAM What the hell is wrong with you? Charlie is devastated. http://www.youtube.com/watch?v=JOAUC-0MV7w Hope the link works this time. The scene works doubly well as this film could have fitted into the discussions about voice over (and flashback). The V.O. in the film is used effectively to convey some of Charlie's thoughts, helping us understand how he feels as the film progresses. In the lead up to this scene we have shared his realisation that the relationship is one-sided and not going anywhere. On a slight tangent, the voice over also helps us share headspace with Charlie and mirrors the "voices" he may be hearing.