THE WEDDING PLANNER (2001)
McConaughey cut his rom-com teeth on this sweet treat starring Jennifer Lopez as a successful San Francisco wedding coordinator who's meticulous (but romantically unfulfilled) life is thrown off course when she falls for a dimpled doctor (McConaughey) who turns out to be a new client's prospective groom. Sure, some of his future romantic comedies have grossed significantly more (Failure to Launch, How to Lose a Guy in 10 Days), but none have been as guileless and charming.
Texas drawl? Yes. Great line: ''Fran is great. But...what if what I think is great, really is great, but not as great as something greater?''
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