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.

First dates between best friends prove to be problematic; Kris demands commitment from Alex; Darion is ready to bail when the date doesn't meet his expectations; Sydney gets a surprise; Marshana puts her pride on the line.

Jin confesses to dating other men; Darion and Charley share an awkward first kiss; Marshana and Stefan try to recreate their first date from four years ago; Kris engages in cyber-stalking with leads to a confrontation with Alex.

Marshana confesses her secret love for Stefan; Sydney woos a skeptical Jin; Charley sneaks off to a party without Darion; Kris gives Alex a list of everything she wants him to change.

Marshana unveils a seductive side as she and Stefan move things into the bedroom; an unexpected guest spoils Charley and Darion's night; Sydney looks forward to finally kissing his best friend, Jin.

Marshana is blissfully happy after spending a night with Stefan; Charley has a wandering eye at the Pride parade; Kris pushes Alex to declare his love; fitness models Greg Plitt and Melanie Marden try their hand at romance.