The Best of the Worst chat-up Lines in Film and TV

This was produced on behalf of eHarmony, America’s leading relationship matchmaking service. Amongst other things, eHarmony reduces the need to engage in terrible chat-up lines.

The chat-up line: so difficult to get right, so easy to get wrong. Why? Because a sentence or two isn’t generally enough to convey an inherent wit, intelligence, confidence and general awesomeness. But is every chat-up line necessarily destined for failure? Or can some lines be so bad as to be good? Take a look at this selection of questionable lines and decide for yourself…


1. “Your husband told me you were the most beautiful woman he’d ever seen, but he didn’t say anything about the most beautiful woman I’d ever seen.”

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Intolerable Cruelty

Trying to chat-up married women isn’t generally a good idea. Invoking their husbands in the process is even worse. Unless, that is, you’re George Clooney. As prominent LA divorce attorney Miles Massey, Clooney is able to deliver his line without it seeming quite as creepy as it should.


2. “Well, this is a very stupid question…”

As Charles in Four Weddings and a Funeral (1994), Hugh Grant is the archetypal bumbling Englishman. His chat-up line is more of a small monologue, and forms part of the spur-of-the-moment school of tactics. What the vid and decide whether it’s charming, nonsensical, or both.


3. “I have crossed oceans of time to find you.”

Despite (nearly) being a pre-cursor to biting her neck, Gary Oldman’s line as Dracula (1992) is pretty impressive. Not much use unless you’re immortal though.

4. “You make me want to be a better man.”

As Melvin Udall in As Good as It Gets (1997), Jack Nicholson is a world weary, misanthropic author. When he delivers his line to long-suffering waitress, Carol Connelly (Helen Hunt), she and the viewer know it comes from the heart – which is something of a rare quality in the pick-up game.

5. “Mind if I get drunk with you?”

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Red Dust

Spoken by Dennis Carson (Clark Gable) in Red Dust (1932), this line works if you’re a rich owner of a rubber plantation in Indochina, and those around you have nothing better to do than while away hot afternoons with a glass or two. It definitely doesn’t work if you’re on a crowded morning bus on the way to work.


6. “I may be an outlaw, darlin’, but you’re the one stealing my heart.”

Delivered at the end of a monologue on how to carry out armed robbery, Brad Pitt’s line as J.D. in Thelma & Louise (1991) just manages to stay on the right side of the cheeseboard.


7. “Let’s hop on the good foot and do the bad thing.”

Though apparent gibberish, the meaning behind Austin Power’s (Mike Myers) line in The Spy Who Shagged Me is all too clear.


You’ve seen a good list of the Worst chat-up Lines in Film and TV…Any Terrible Movie Pickup Lines We Missed?

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