The Wedding Date (2005)

When all else fails, hire a male escort. It’s been two years since Kat Ellis (Debra Messing) was dumped by her ex-fiancée Jeffrey (Jeremy Sheffield). Now that her younger half-sister (Amy Adams) is getting married, who is the groom’s best man? None other than Jeffrey. Of course Kat has to let him see that she has not only moved on, but has a new, handsome man in her life.