50 Worst Movie Ex-Boyfriends

John Willoughby (Sense And Sensibility)

The Ex-Boyfriend: Dashing John Willoughby has all a nineteenth century gal could wish for: good looks, outspoken views on art and culture, and the ability to scoop up and carry home a damsel in distress.

His Post-Break-up Behaviour: Although Willoughby is practically engaged to Marianne Dashwood, the deceitful love-rat ditches her quickly for for the extremely wealthy Miss Grey after he is disinherited for siring an illegitimate child. He then starts to snub the Dashwood sisters at parties as if he never even knew them.

Tom Hansen (500 Days Of Summer)

The Ex-Boyfriend: Hopeless romantic Tom (Joseph Gordon Levitt) hooks up with the world’s most perfect girl next door, Summer (Zoe Deschanel), while they’re working at a greetings card company.

His Post-Break-up Behaviour: Tom is dumped by Summer when their relationship begins to crumble. This sends him into a deep depression. From sporadically shouting aloud his disgust in songs that remind him of her to filling greetings cards with cynical messages, Tom acts out all of our worst ex-boy/girlfriend traits. Damn you, Tom.

Chip (The Ex)

The Ex-Boyfriend: Wheelchair-bound ad-man Chip conspires to win back his former love Sophia when she and her husband move back into town.

His Post-Break-up Behaviour: After failing to persuade Sophia to run away to Spain with him, Chip reveals he doesn’t really need a wheelchair and claims that he faked it in bed with her when they were together.

Joel Barish (Eternal Sunshine Of The Spotless Mind)

The Ex-Boyfriend: Intensely shy yet talented doodler Joel Barish is drawn to the colourful-haired, free spirit Clementine.

His Post-Break-up Behaviour: After a particularly nasty fight, Clementine pays to have Joel erased from her memory forever. When Joel discovers this, he decides he wants the same. Whereas slightly unhinged Clementine does this because she’s hurt, Joel appears to have his mind erased out of anger and spite. He also says some pretty hurtful stuff when he’s off-loading.

Brendan Block (Secret Smile)

The Ex-Boyfriend: In this TV movie, David Tennant brings the creepy as Brendan Block. Brendan is a very keen boyfriend who after dating Miranda for 10 days, thinks it’s the right time to let himself into her flat and make his way through her teenage diaries.

His Post-Break-up Behaviour: Obviously Miranda gives Brendon the boot. What does Brendon do? He weaves his way back into her life by getting engaged to her sister, exercising a worrying influence on her suicidal brother, getting her arrested for harassment and raping her.

C.K. Dexter Haven (The Philadelphia Story)

The Ex-Boyfriend: C.K. Dexter Haven is the ex-husband of Philadelphia socialite Tracy, who is about to marry another man.

His Post-Break-up Behaviour: Dexter was ditched by Tracy for being an alcoholic (there are also jokey references to wife beating). He then annoyingly shows up just before her new nuptials, all charming and in with her family. Believing in his change and seeing him in a new light, Tracy takes Dexter back. Which is fairly forgivable as he is Cary Grant.

Kevin (Meet The Parents)

The Ex-Boyfriend: Kevin (Owen Wilson) is the jesus-loving, wealthy investment banker, amateur carpenter ex-fiancee of Pam, who has since moved on to male nurse Greg.

His Post-Break-up Behaviour: Although Pam left Kevin a while ago, he manages to embroil himself in her family, acting as her brother-in-law’s best man. He flaunts his large house and excessive amount of photos of Pam to Greg and then openly reminisces about how Pam was a “Tom Cat”.

Mickey (Hannah And Her Sisters)

The Ex-Boyfriend: Mickey is a hypochondriac television producer who struggles with the meaning of life after a brain tumour scare.

His Post-Break-up Behaviour: Mickey and Hannah’s marriage struggles through infertility and eventually ends. Although Hannah remarries, Mickey still bothers her with his hypochondria and existential crises. He then marries her sister and gets her pregnant.

Jacob Helm (Like Crazy)

The Ex-Boyfriend : Jacob Helm is a Los Angeles college student who begins a relationship with British exchange student Anna. The pair become inseparable causing Anna to overstay her student visa.

His Post-Break-up Behaviour: After the visa fiasco, Anna is banned from reentering the United States so eventually the couple calls it quits. Technically Jacob could just move to England, if he really wanted. Instead, he and Anna continue to drift in and out of a painful long-distance relationship until she is eventually allowed back into America.

Bill (Kill Bill)

The Ex-Boyfriend: Bill is the leader of the Deadly Viper Assassination Squad and the ex-lover of former squad member The Bride.

His Post-Break-up Behaviour: When The Bride leaves her profession and dumps Bill to start a new life with her unborn child, he attempts to take her out at her wedding rehearsal.

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