Wedding Daze (2006)

After a sudden proposal ends in tragedy, Anderson is sure he will never fall in love again. His best friend keeps pushing him to meet someone new, but Anderson cannot stop talking about the woman he lost. Then, in a diner and under pressure to move on, he blurts out a proposal to Katie, a dissatisfied waitress. To his surprise, she says yes, turning a reckless dare into an unexpected chance at love.