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The Neurotic Clown, French Kiss (1995)
Kate (Meg Ryan) is an uptight, supremely organized, lactose-intolerant history teacher whose life plans go out the window when her fiancé (Timothy Hutton) ditches her for a woman he meets in France. She sucks up her fear of flying to go win him back and inadvertently smuggles in a stolen necklace for French lout Luc (Kevin Kline).
Unbelievable: That Kate is somehow both a really put-together person and also a total clown (Luc's words), always on the verge of throwing her body around in spasms, falls, or fits of disgruntlement. She's also willing to give up basically all the things she values (safety, stability, politeness) for men.
Watch French Kiss on Amazon with a Starz subscription.
Every Man's Ideal, There's Something About Mary (1998)
Ted (Ben Stiller) tracks down his lifelong crush, Mary (Cameron Diaz), whom he hasn't seen since their ill-fated prom night. She's a gorgeous orthopedic surgeon living in Miami, pursued nonstop by all the men she charms.
Unbelievable: We buy this perfect girl's relentless niceness to the underdog, fueled by her love for her autistic brother, and even the fact that she is into everything guys love. What we can't swallow is her willingness to consider being with Ted after discovering that his obsession drove him to hire a detective to find and stalk her.
Watch There's Something About Mary on Amazon.
The Humble Movie Star, Notting Hill (1999)
Anna (Julia Roberts) is a beautiful movie star who literally runs into bookstore owner Will (Hugh Grant) in London and decides to date him, with their first date being his sister's birthday dinner party.
Unbelievable: While there actually are plenty of movie stars who marry civilians, it's difficult to imagine a woman as successful as Anna not getting fed up with Will's weak, indecisive nature.
Watch Notting Hill on Netflix.
The Not-Quite-Homewrecker, The Wedding Planner (2001)
Mary (Jennifer Lopez) is a wedding planner who accidentally falls in love with the groom (Matthew McConaughey) of her biggest client after one sort-of accidental date. Clumsy shenanigans ensue.
Unbelievable: In her work, Mary should be exposed to all kinds of couples who aren't meant for each other, and yet she makes the flaky decision to agree to marry some guy (Justin Chambers) just because her dad likes him and because the other guy isn't available.
Watch The Wedding Planner on Amazon.
The Small-Town Traitor, Sweet Home Alabama (2002)
Melanie (Reese Witherspoon) is a successful fashion designer living in New York City and engaged to the mayor's son. The only problem is she's still married to her childhood sweetheart in Alabama.
Unbelievable: This whole movie posits that an ambitious, smart woman like Melanie has decided that in order to live in New York, she had to stop speaking to everyone she knew back home. We may not love visiting our own hometown, but pretending that it (and the exes left behind) don't even exist suggests she's suffered some kind of psychotic break — or perhaps a seriously abusive situation.
Watch Sweet Home Alabama on Amazon.