She's Out of His Mind (2011)

It's the eve of the Las Vegas wedding of his close friend Judy Claymore and Roland Hayes juggles a host of conflicting emotions while pacing in his hotel room. He is amazed by the arrival of the bride-to-be herself, but much unfinished business remains between them. Their joyful reunion is interrupted by a gruff delivery man bearing Roland's order of Chinese food and a truckload of wry observations on women, relationships, and why a Sinatra ballad is ideal for disrupting a wedding ceremony. Over the course of the weekend Roland is visited -- "confronted" is probably a better word -- by all the women lurking in his past in a series of surreal comic vignettes. He grapples with his reluctance to let them go and his fears about the future. In the end he is able to let go of worn-out old dreams and make room for new ones -- and for new love.