Wedding Daze (2006) on Netflix

Plot summary

Anderson's best friend Ted tells him he has mourned the girlfriend he lost for longer than the two of them were ever together, and urges him to give romance another try. At the diner where they are eating, Anderson asks Katie, the waitress, to marry him, and she says yes. The evening before, Katie had played charades with her boyfriend William, her mother Lois and her stepfather Stuart, and the phrase she had to guess was "Will you marry me?" She visited her father Smitty in prison for advice, and he told her to listen to her heart. She and Anderson walk and talk, and she is the one who proposes to him. She moves into his apartment the same day.