Watch Made of Honor

Patrick Dempsey plays Tom Bailey, who doesn't believe in long term relationships. He meets Hannah (Michelle Monaghan) after he gets into bed with her by mistake. They become instant friends due to Hannah's honesty. They remain friends over the course of the next ten years even though Tom hops from one woman's bed to another. Tom is a very wealthy man after he invents the coffee collar. Hannah is a painter at a museum. Tom attends his father's sixth wedding with Hannah. His father is getting married to a brainless blonde with huge boobs. At the reception, Hannah tells Tom that she is leaving for a long business trip to Scotland. The realization hits Tom hard that he really loves Hannah. He wants to declare his love as soon as she returns home.

The two are meeting for lunch when Tom gets the shocking news that Hannah is engaged. She has met Colin (Kevin McKidd) while in Scotland. Because Tom is her best friend she asks him to be her maid of honor. He agrees with the thoughts that he will get to have more time with Hannah. He tries his best to convince Hannah that she is not in love with Colin. After going through all the wedding shenanigans, they go to Scotland where Tom endures more humiliation and disappointment with Hannah.

The bachelorette party is a turning point for Tom. A passionate kiss is exchanged, and Hannah is confused by its meaning. After several misunderstandings they begin to talk, and Tom confesses his feelings for her. Tom can't watch Hannah marry Colin, and so he goes home. At the wedding, the priest asks if anyone objects. Tom returns on horseback, and flies through the doors, falling off the horse. Hannah runs to him, and he tells her that he loves her dearly. They kiss, and Hannah apologizes to Colin, because she can't marry him. Tom and Hannah end the movie by getting married.