(Sept. 15, 2015) — Well, today’s the day, kiddies: the second season of the award-winning series EastSiders debuts on Vimeo On Demand. The next chapter in Kit Williamson’s saga of love, infidelity and figuring it all out is deeply, darkly funny but also complex and multi-layered. Its twists and turns are unexpected, but it hews true to what you want from a sophomore outing: familiar, yet boldly different. And frankly, that’s harder to do than you might expect.

(rear, l-r) Matthew McKelligon, Willam Belli, Satya Bhabha and Stephen Guarino and (front, l-r) Adam Bucci, Kit Williamson, Van Hansis and John Halbach star in the smart, funny and moving second series of EastSiders.

This season begins with Thom (Van Hansis) and Cal (Kit Williamson) in bed. Strange, you may think. After all, they broke up at the end of season one. The shot then opens wider to reveal someone else in the bed with them. Oh. Well. This is different. And with that establishing moment, we’re off to the races.

Season two opens up new vistas, explores characters in ways that we don’t ordinarily see or, in many cases, that we may have never seen before. In the aftermath of the infidelities that broke them up, Cal and Thom still find themselves drawn to one another even as they find their lives changing — “inexorably” is the qualifying adverb that Cal uses multiple times — and they begin to date again. But, more willing to push the boundaries of a “traditional” relationship than they were previously, they begin to experiment.

“I wanted to break open the love triangle,” said writer/director/star Williamson. “Jealousy is only interesting to a point. What happens when it’s removed from the equation?”

Adam Bucci as Trevor, Matthew McKelligon as Jeremy and Satya Bhabha as Jarred assist creator Kit Williamson in his quest to “break open the love triangle” as Thom and Cal explore new sexual horizons in season two.

As Thom and Cal attempt to navigate the unwritten rules of morning-after protocol post-first threesome — a shower? a hot breakfast? — we find the man who was the catalyst for Thom and Cal’s breakup, Jeremy (Matthew McKelligon), having a new fling and Ian (John Halbach), who has just broken up with “Krazy Kathy,” drowning his sorrows in whiskey and eggs — and an unexpected liaison — at brunch.

The first episode also introduces us to a few of the key characters who add substance to the second season, including Cal’s sister Hillary, whose introductory scenes are played in hilarious fashion, almost as a delicately rendered but slightly unhinged aria, by Brianna Brown and Thom’s new co-worker Jarred, played with a nice, light touch by Satya Bhabha.

Adhering to the same non-linear track that worked so well in the first season, the second episode of this season takes us back a day and shows us how we arrived at the events seen in episode one. Kathy (the magnificent Constance Wu) is back just long enough for her and Ian to end things before leaving on the non-Equity tour of Cats. “It’s a really great opportunity.” (This may not be terribly funny to you, but to anyone who has ever spent any time in the theatre, it’s hilarious!) Party promoter Quincy (Stephen Guarino), who threw the Mayan Apocalypse party in season one, has a more substantial role here alongside the indescribable wonder that is Willam Belli as Douglas.

It’s in this episode that you begin to see Williamson’s masterful plotting begin to take shape as unexpected threads are pulled and the tapestry begins to take a more complex and quite unanticipated shape. It’s all clever enough to leave you eagerly awaiting the next installment.

The central focus of EastSiders is on Kit Williamson as Cal and Van Hansis as Thom, who show us just how well they have mastered their craft in the second season of this witty and boundary-pushing dark comedy.

And the fun really begins here. It’s a lighter feeling throughout as this part of the story is advanced through a series of sexual encounters that are adroitly edited together, revealing the pitfalls, trepidations and revelations that come with this type of experimentation. Jarred — not only a waiter but also a sex therapist-in-training — weaves into and out of the narrative (and the bed) like an adorable ‘sex Yoda’ as Cal and Thom set out to sleep their way through Silver Lake, actions which seem at odds with Cal’s prior declaration that “life is not a gay porn.”

Meanwhile, Guarino and Belli perform a completely demented comic double act and Jonny McGovern’s hilariously deadpan cameo is a laugh-out-loud highlight. More threads are subtly pulled and the first half of the season ends tenderly with a warm, loving scene between Cal and Thom.

EastSiders never fails to astonish. There is a mastery of character and story arc here that you simply don’t expect. And even more astonishing, no one ever hits anything approaching a wrong note: every scene rings bell-clear, every intention is realized, every mark is hit. Also, in almost every indie production, you expect there to be at least one actor — you know, that last-second third-replacement who agreed to work for a $5 footlong and a bus pass — who really should be thinking about other career options; but not so here.

In fact, if anything, Williamson and Hansis are playing at an even higher level than they were in season one. Hansis, in particular, seems completely effortless and effervescent in his portrayal. Thom is on a high thus far in the series and watching Hansis assay this role is a sheer and utter delight and Williamson matches him note for note in an ovation-worthy pas de deux.

Look, I know that sounds like a lot of over-the-top folderol, but it’s really not. I defy you to disagree with me once you’ve seen it.

As for Williamson, well, the world is that boy’s oyster. It’s one thing to be a good actor. Or a smart writer. Or an inventive director. But to be all three? And a producer, to boot? I’m so excited to see what he does over the next 20 or so years. Whatever it is, I have absolutely no doubt that he’ll show all of us up.

Raising money through Kickstarter, Williamson has said, has allowed him to “make the show exactly how I had envisioned it. Crowd-funding is a game changer for stories like ours that don’t often receive traditional financing from studios and TV networks.” And it shows. The authenticity of the story is here in a way that you seldom, if ever, see in something sanitized or whitewashed by networks or funders.

As the first episode draws to a close and Thom and Cal have decided to “officially” reunite, Thom says, “I didn’t know what this was going to be.” Cal replies, “I still don’t.” “Then,” asks Thom, “maybe we can figure it out together?” And ultimately, that’s really what the entire show is about: figuring everything out. It’s something we’re all trying to do. Perhaps that’s what we’re all supposed to do. Or at least try to do: grow up, partner up and figure out something that works. For us.

I can’t wait to see what life throws at Thom and Cal next. I hope you can’t either.

EastSiders premieres today exclusively on Vimeo On Demand. Wolfe Video will release the series on DVD and across additional digital platforms beginning Nov. 3. If you need a season one refresher, click here.

PS — For the record, Summer Clearance and Amber Alert are two of the best drag names I’ve ever heard.

Read more about the rest of EastSiders season two here.

If you just can’t get enough Van Hansis and Kit Williamson, this Friday, the film Kiss Me, Kill Me has its world premiere at Reeling2015, Chicago’s LGBT film festival. Brianna Brown and Jai Rodriguez from EastSiders also appear alongside Hansis, WIlliamson and Queer as Folk’s Gale Harold in this Casper Andreas-directed, David Michael Barrett-penned murder mystery caper.

A Few Previous Related Postings:
Kit and Van and Cal and Thom and … Cassandra?, May 2014
Why I’m Supporting EastSiders — And Why You Should, Too, April 2014
Kickstart This — EastSiders Needs You, Jan. 2013
EastSiders — New Web Series Worth Watching, Dec. 2012