The Wedding Date (2005)

Get ready for a delightful mix of romance, humor, and unexpected chemistry in The Wedding Date, a heartwarming romantic comedy directed by Clare Kilner. This film is the perfect choice for anyone who loves a feel-good story with a dose of charm and a sprinkle of wit.
Debra (Debra Messing), a successful but lovelorn woman, has a serious problem: she’s been invited to her sister’s lavish wedding, but her ex-fiancé is also attending, and it’s bound to stir up painful memories. In a moment of desperation, she hires a handsome, smooth-talking escort, Nick (Dermot Mulroney), to accompany her as her date and help her face her ex with grace and confidence.
As they attend the wedding together, sparks fly between Debra and Nick, and what starts as a business arrangement quickly turns into something much more complicated. But with a fake romance on the line, Debra is forced to confront her feelings, her insecurities, and the truth about what she really wants in love and life.

Nick is a professional “wedding date” for hire—someone who accompanies women to events like weddings and helps them navigate social situations. As the two spend time together, their initial business relationship grows into something more, as Kat begins to open up about her fears and insecurities, and Nick’s charm and wit win her over.