History follows Jamie, a thirty-something gay New York lawyer, in the days after a messy breakup with his partner of five years, Jared. Through juxtaposed flashbacks, the audience watches Jamie’s evolution—or lack thereof—on issues of intimacy, sex, gender role conformity and friendships as he rebuilds his life on his own terms.
Jamie jumps right out of a five year relationship into the arms of Joshua, causing long-time friends Bianca and Catherine to grow concerned.
Jamie throws himself back into the dating world, while also calling on an old hookup, but the emotional impact of the recent breakup forces him to understand his impulse to engage in no strings attached sex.
Jamie starts new friendships, meeting Matthew and Gio at a Pride party, and steers his relationship with William towards a friendship. But when Jamie meets Matthew's friend circle, he finds Brian's treatment of his boyfriend disgusting, and yet also familiar.
Jamie skirts William's questions about his old friend group and recent move into a new apartment. After William explains his view of friendships, Jamie makes a choice.
Jamie brings William and Matthew to a RuPaul's Drag Race viewing party at Ted's place. In the midst of Jamie's struggle over whether he can be the "top" in a relationship, William's Grindr profile hits a sore spot.
When Jamie and Jared end up on the same train, Jamie seeks advice from his friends on what to do, and answers to why he's still so angry.