Four sets of friends risk it all when they try dating each other for the first time. In New York, a secret crush is revealed when Alex asks out Kris, his best friend of 8 years. Meanwhile Marshana hints to recently separated Stefan that her feelings may be more than just platonic. In Los Angeles, newly-single Charley asks his bestie Darion to be more than friends, while lovesick Sydney chases best friend and single mom Jin, whose ex-husband lives in her basement.