It's Valentine's Day and Tom has big plans. He's about to get engaged and has a surprise party planned to share the good news with friends. But things take a turn for the worse. Tom returns home only to discover his girlfriend has packed up and left him. Now, instead of a surprise party, the surprise is on Tom. Fortunately, his friends are there to help him make sense of it all.
Cuba Gooding Jr.
Tom
Matthew Lillard
Sal
Sean Astin
Geroge
Terrence 'T.C.' Carson
Kwame
Anne Heche
Laura
Gina Gershon
Rachel
Tamala Jones
Katherine
Shiri Appleby
Debbie
Jud Tylor
Amy
It's Valentine's Day and Tom has big plans. He's about to get engaged and has a surprise party planned to share the good news with friends. But things take a turn for the worse. Tom returns home only to discover his girlfriend has packed up and left him. Now, instead of a surprise party, the surprise is on Tom. Fortunately, his friends are there to help him make sense of it all.
Bart's chance encounter with the enigmatic Vienna leads to a whirlwind weekend together. The two fall fast and hard, but both carry secrets that could be their undoing or the chance for a fresh start.
With varying degrees of success, recently divorced friends Dave, Vic and Donny are trying to move on with their lives. Vic feels vilified by his ex-wife's parents, while Donny has a shaky bond with his teen daughter, Emma. Dave, meanwhile, has an enviable problem -- he has more dates than he can handle. As they confront their post-marital challenges, the men take solace in one another's plights.
Lori and Doug break up right before Lori's sister's wedding and decide to pretend they're still together for the weekend as to not disrupt the fun.
Avery, a teenager with a tendency towards perfectionism, enlists her friend Larson to help her prepare for her first time with her long-distance boyfriend.
A panicked young woman and her two best friends fly to Mexico to delete a ranting email she sent to her new boyfriend. On arrival, they run into her former beau, who soon gets caught up in their frantic scheme.
Burned by a bad breakup, a struggling New York City playwright makes an unlikely connection with a divorced app designer she meets on a blind date.
Lu, a conformist woman in her forties, learns that her 15-year partner has been having extramarital affairs. Starting from scratch, she gets involved in an unexpected relationship with a young womanizer.
A stubborn idealist spies a bride on her way to her wedding and immediately falls in love with her.
In college, Dex was the big man on campus. Ten years later, now an overweight kindergarten teacher, Dex is immune to the shocked stares of the women who were once his conquests. While trying to pick up the bartender, he is struck by the gorgeous Syd. Through a series of circumstances, Syd and Dex are thrown together and he soon finds himself questioning his belief in all things Steve.
After her fiance sleeps with a celebrity on his free pass list, Abby Meyers, with nothing but five names and a fantasy shared by millions, sets out for Los Angeles to sleep with someone from hers.