That Awkward Moment (2014)

Plot: Twentysomethings Mikey, a doctor, and Jason and Daniel, who work together as book cover designers for a publishing house, are best buddies. After Mikey's wife Vera divorces him, she having fallen out of love with him and in love with someone else, Jason suggests that the three of them enter into a pact to be single, namely to amass a proverbial little black book of women, each individual woman who each will not see more than twice a week in keeping things casual. Shortly after making this pact, Jason reconnects with an author named Ellie, who he is able to charm despite the misconception by Jason during what ended up being a one nighter, their resulting relationship which slowly crosses the line of the pact. Daniel and his longtime friend Chelsea - who have acted as each other's wing person in picking up potential sex partners - end up seeing each other in a different, more romantic light. Neither Jason or Daniel want to disclose to their friends what seem to be their burgeoning serious relationships. Conversely, Mike, still pining after Vera, ends up reconnecting with her in ways they hadn't in months, he too reluctant to disclose to his friends what he is doing with his ex-wife. For Daniel and especially Jason, the most ardent bachelor, they have to decide how far they will go to hide or deny their relationships, which if they go too far might actually jeopardize what they truly want in life with who they truly want in life. And Mike has to come to a realization if his reunion with Vera is truly what he wants, or if it is him falling back into the path he had determined with her since they were in college.