“Eastsiders” Season 2 Trailer Brings Open Relationships, New Loves And Willam Belli

"You don't get to pick and choose the shit that you don't want to deal with."

Eastsiders is back: The acclaimed web series following boyfriends Cal and Thom as they navigate their relationship after an infidelity, returns on September 15, exclusively on Video on Demand.

A new trailer reveals that creator Kit Williamson (Mad Men) has turned up the show’s star power, with appearances from Drag Race faves Willam Belli and Manila Luzon, plus Drew Droege, Traci Lords, Jai Rodriguez, Firefly’s Sean Maher, and Matthew Wilkas of the indie gay hit Gayby).

eastsiders Willam Belli

That’s in addition to returning cast members Constance Wu (Fresh Off the Boat) and Stephen Guarino (Happy Endings).

Williamson also turned up the heat—as Cal and Theo explore opening up their relationship sexually and uncover the complexities of dating an ex.

“Jealousy is only interesting to a point,” explained Williamson. “What happens when it’s removed from the equation? There are so many different ways human beings connect with each other, and there is no one way that is right for everybody. The show explores many different kinds of relationships, from ex-boyfriends getting back together, to friends starting a new relationship, to a lesbian couple with two kids finally getting married.”


Season One of Eastsiders appeared on YouTube, NewNowNext and Logo TV, but after a successful $150,000 Kickstarter campaign, Williamson decided to go the independent route for Season 2.

“I was inspired by the enormous success Vimeo has had with shows like High Maintenance,” he explained. “As an independent filmmaker, I appreciate the autonomy streaming services afford content creators.”

Watch the trailer for Eastsiders Season 2 below

Dan Avery is a writer-editor who focuses on culture, breaking news and LGBT rights. His work has appeared in Newsweek, The New York Times, Time Out New York, The Advocate and elsewhere.