EastSiders, the critically-acclaimed dark comedy starring series creator Kit Williamson (Mad Men) and three-time Emmy Nominee Van Hansis (As the World Turns) as a gay couple trying to stay together in the aftermath of infidelity, returns for its second season

The trailer turns up the heat on Cal and Thom’s relationship, as they explore opening things up sexually. It also hints at the dramatic complexities of dating an ex.

“I wanted to break open the love triangle,” explained Williamson, “jealousy is only interesting to a point. 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.”

The second season of EastSiders is being called funnier than the first, but also tackles some very dark topics, from heartbreak to infidelity to STDS.

The large ensemble cast includes Constance Wu (playing a character very different from her role as the conservative mother on ABC’s Fresh Off the Boat), Matthew McKelligon (You’re Killing Me), John Halbach (Wallflowers), and Stephen Guarino (Derek on Happy Endings), all returning in their starring roles. Joining them for season two are Willam Belli (RuPaul’s Drag Race), Brianna Brown (Devious Maids), Brea Grant (Heroes) and Vera Miao (State of Affairs).

The season boasts a number of incredible guest stars, including Traci Lords, Lennon Parham (from USA’s Playing House), Sean Maher (Firefly), Jai Rodriguez (Kingdom), David Blue (Stargate Universe), Leith Burke (The Haves and the Have Nots), Matthew Wilkas (Gayby), Satya Bhabha (New Girl), Manila Luzon (RuPaul’s Drag Race) and Drew Droege, from the viral hit Chloe videos.

Since its debut, the show has leapt across several different viewing platforms, appearing first on YouTube, then LogoTV.com, a subsidiary of Viacom. The feature film version of the series aired on Logo’s cable network and was then distributed on DVD and digital platforms through Wolfe Video. The second season premiered on Vimeo on Demand on September 15. Wolfe Video will release the series on DVD and across additional digital platforms beginning November 3.

“I was inspired by the enormous success Vimeo has had with shows like High Maintenance,” explains Kit Williamson of his decision to move EastSiders to the streaming network. He believes the rise of streaming services like Netflix, Amazon, Hulu and Vimeo has blurred the line between TV and web and credits the crowdfunding website Kickstarter with making independent television shows like his possible.

“Like many in my generation, I watch TV online,” he says. “As an independent filmmaker, I appreciate the autonomy streaming services afford content creators. And thanks to our amazing Kickstarter backers, I was able to make the show exactly how I had envisioned it. Crowdfunding is a game-changer for stories like ours that don’t often receive traditional financing from studios and TV networks.”

Additionally, it hasn’t escaped Williamson that the streaming networks have become a conduit for independent series like his to be picked up by the major cable channels. High Maintenance, a series that aired its first nineteen episodes on Vimeo, will premiere on HBO later this year.  Williamson has similar goals.

“Our audience has followed us from YouTube to cable to iTunes, Amazon and Hulu. I’m hopeful that they will remain on this crazy rollercoaster with us as we transition to Vimeo On Demand and beyond.”

EastSiders explores the drunken outbursts and double standards of twenty-somethings living and loving in Silverlake, CA. The series has won several awards including Best Web Drama from LA Weekly Web Awards and the Indie Series Award for Best Ensemble. It received a Satellite Award nomination from the International Press Academy.