A gem!!! I stumbled upon this film by accident. Lizzy Caplan is believable as the robotic/cold woman who tries to follow her confused heart by hurting other's. Their is a balance of you empathizing with her and sympathizing with Geoffrey Attend and Mark Webber.
Smart, beautiful and headstrong, Alexis is the girl of Dustin's dreams. But after only five weeks of dating, the love-struck Dustin is coming on so strong that Alexis is forced to slow things down - permanently. Devastated and desperate to get her back, Dustin turns to his best friend, Tank, the rebound specialist. A master at seducing - and offending - women, Tank gets hired by freshly dumped guys to take their ex-girlfriends out on the worst date of their lives - an experience so horrible it sends them running gratefully back to their beaus. But when Tank works his magic on Alexis, he ends up meeting the challenge of a lifetime. Alexis is the first girl who knows how to call his bluff, and Tank soon finds himself torn between his loyalty to Dustin and a strange new attraction to his best friend's girl.
When Lucy (Alison Brie) tells a married Clint (Colin Hanks) that she loves him, he falls into a mysterious hole that suddenly appears in the middle of her living room. As Lucy desperately tries to save Clint, Rydell (Justin Chatwin) appears, looking to settle Clint’s gambling debt. Now Lucy must distract Rydell, the town and Clint’s wife from finding out about her affair and the hole, while trying to hold herself together in the process.
Charlie (Terrence J) is a bachelor who's convinced that relationships are dead despite his therapist sister’s (Paula Patton) and his friends’ attempts to tell him otherwise. On a bet he decides to stay with one woman for one month to prove that he is immune to love. Soon, he meets the beautiful and mysterious Eva (Cassie Ventura) and coaxes her into a casual affair. But as Charlie spends more time with Eva, he begins to question whether he may actually want more than just a one-night-stand.
There’s a right way to be single, a wrong way to be single, and then…there’s Alice. And Robin. Lucy. Meg. Tom. David. New York City is full of lonely hearts seeking the right match, be it a love connection, a hook-up, or something in the middle. And somewhere between the teasing texts and one-night stands, what these unmarrieds all have in common is the need to learn how to be single in a world filled with ever-evolving definitions of love. Sleeping around in the city that never sleeps was never so much fun.