Who doesn’t love beards and benches? Who doesn’t love quirky-yet-relatable conversations between friends? Who doesn’t love Philadelphia? (Probably a lot of people, actually—don’t answer that last one.)

My Ruined Life has all of these and so much more. The local FirstGlance award-winning web series had its Season 2 Premiere Saturday night at L’etage, above Beau Monde on Bainbridge and I was in attendance, among a few dozen other fans, friends, cast, and crew.

First, a bit about the show. My Ruined Life is a short web series about two friends, Brian (Brian Crowden) and Nate (Nathan Holt), who sit on benches and talk about their quirky, messed up lives on benches around Philadelphia. Brian often plays the straight man, weird as he is himself, to the indescribable oddball that is Nate, who often has encounters with what seems to be a mental projection of his inner-thoughts (manifested as the Man in a Tux with a Beard, played by Greg Bailey). The series features the two having humorous slice-of-life conversations in various outdoor locations around the city, always revealing a bit more about their characters and the interactions they have in the worlds they live in off-screen.

Now, the party:

I arrived at about 5pm and already a small crowd had gathered inside, milling around the bar of the classily low-lit club venue. The atmosphere was jovial as more and more people started filing in. I had an awkward mishap with my drink ticket (this was my first experience with drink tickets) and I planted myself in a corner, clumsily observing the party-goers. Lee Porter, the creator of the series, was an affable and incredibly social host, flitting around from person to person.

As an awkward novice journalist, I waited patiently for an opportunity to score an interview with a cast or crew member, and when I saw it I pounced. I introduced myself to one of the two main stars of My Ruined Life, Brian Cowden, and pulled him away into a quiet corner with me to talk about the series (which he was graciously happy to do, I might add):

Matt Aukamp: Brian, how do you feel about Season 2? What are the differences between it and Season 1?

Brian Cowden: I’m excited about it because in Season 1, we didn’t really know what this was going to be. We didn’t know the dynamics between all of us. It was shot in three days and it was our first time with the characters and our first time working with Lee… And this one we shot twelve episodes in two days and it went so much smoother than it went the first time.

Matt: Did you still manage to travel around Philadelphia as much?

Brian: We traveled around more, actually. We shot in four different locations and with all that travel, usually, it’s hard to coordinate but it was really smooth and we were really on top of it. Me and Nate knew our dynamics and because we had that anchor going in, adding [the new character] Kristen—[a manifestation of my character’s subconscious] just like [the Man in a Tux with a Beard is a manifestation of Nate’s subconscious]—was very seamless. The foundation was there this time. It was more defined and we could play a little more.

Matt: Is there more improvisation in this season?

Brian: Yeah! There were certain parts where Lee chose not to write because he figured out – after Season 1 – that we riffed off each other really well. So he was like, “I don’t have anything written for this part of the scene, but I figure you guys will banter and we’ll just keep the camera rolling.” And that’s what we did. I’ve never had something go so smoothly. And in such dire heat! We shot in mid-July and I was outside on a bench with a button-down shirt on and a tie, sweating profusely.

Matt: Is there anything you think will be surprising to people in this season?

Brian: We find out a little more about Nate’s job. And there are some local celebrity appearances. Ben Franklin makes an appearance. Which is pretty awesome, and was very weird to shoot. And hopefully this season we see a little bit more of Philly and its benches. They range from over on the Waterfront to U Penn’s campus to Drexel and even down to Northern Liberties. So we jump around a good bit. And having Kristen enter and having her act with Greg Bailey’s character – it’s just expanding.

Soon, Lee came over and introduced me to Greg Bailey (Man with Beard in Tux) and Kristen Egermeier (Kristen) and we talked briefly about the differences between the first and second seasons:

Greg Bailey: You know, I think Season 2 is much more refined. We knew what was going on and so we had more time to sort of play with it and I think that made it much looser.

Matt: Kristen, had you seen Season 1 before you joined the cast?

Kristen Egermeier: Yeah. When Lee first asked me to audition, I watched it all. I think it’s kind of fun to be able to watch them back-to-back so you can see the [thematic] thread coming along and see them all progressing.

Matt: So how did it meet your expectations?

Kristen: It was interesting because I wasn’t sure how the dynamic would change since I’m the only girl. And [entering] this “bro-hood” who all know each other very well, I was like “I don’t know how it’s going to be adding this new addition.” But it really just carried on and it made sense, especially as a compliment to Greg’s character. I think it’s a great follow-up.

Matt: Is there anything people should specifically look for in Season 2?

Kristen: I think questions will be raised.

[Laughter] (I laughed along, but I’m not quite sure what the joke was, as I haven’t seen the season yet. Were they making fun of me? I don’t know… They probably all hate me now…)

Greg: The same questions that were raised in Season 1 are going to be raised in Season 2 and the question is going to be, “What is going on?”

Matt: Is there anything else you want to say about Season 2?

Greg: Honestly, I think it’s going to be better. Though I liked Season 1. I was in it.

[Laughter] (I got that one.)

Kristen: I liked Season 1 too!

Greg: I just felt that Season 2 will be the better of the two seasons. Especially with Kristen. I remember when she first came on, we had met at Lee’s house and Lee was like “She’s willing to do whatever crazy thing we want her to do!”

Kristen: They kept asking me if it what they were going to have me do was OK, and I was thinking,“This isn’t crazy!” and also, “What is my limitation for crazy?”

As the lights started dimming, we had to wrap up the conversation. I accidentally called Kristen “Lee” (which is on tape and very embarrassing), and we all found our seats, waiting for the premiere to begin. I planted myself in the “Reserved” section, which was a bunch of empty seats and me, sitting awkwardly on the corner of a cushioned seat pouf, as if to say, “I’m just resting here because it’s the first place I saw. I could get back up at any second, if someone more important comes and you need me to move.” Many other people sat around or stood at the bar or behind the seating area. The room hushed as two trailers and, subsequently, three full episodes played.

About the episodes: If you’re a fan of the first season, you will not be disappointed. Everything everyone said to me about this season being even more “fun” and “playful” came through from the first moments of the premiere. The energy was stronger. The characters, more comfortable in their roles. The writing was sharper. And the amazingly cohesive tone the whole series had since the first episode was sustained and furthered in a seemingly effortless way.

Afterward, people milled about for the next hour, chatting about the episodes. “Oh man, you didn’t see Season 1? Then you must not have understood all the jokes about the baby wipes and the elastic shorts!” was one thing I overheard. I met Nero Catalano, who wrote the theme music for the show, part of the glue that holds the aforementioned “cohesive tone” together. I also met the series’ video editor Sean Huber, local musician, improviser, and filmmaker. As I drifted around, talking to these people, the thing that struck me was how many talented and interesting people with ties to local music, improv, and theater scenes My Ruined Life has working on it. It really makes you root for the show and its cast and crew.

As things began to dwindle down around 7-7:30, I started to make my way out. I had left him alone the majority of the night, as he was the man of the moment and constantly rushing around talking to people, making sure everything went smoothly (and it did). But now it was time to get some words from Lee Porter, who, at this point, was probably exhausted. Here’s what Lee had to say:

Lee Porter: This started as something of a personal project. I got frustrated as a writer who’s written multiple novels and screenplays, knowing deep down that the first five pages – if I’m lucky – are being read by an intern who’s never going to recommend them further. And I know that my favorite joke is on page 60 or page 75 and it’s never getting read. And it happens so many times. I [started to] dread going to a movie and seeing somebody doing something where I’m like “Ahh! I’ve had that and it’s been in a screenplay for five years and now it’s never hitting pay dirt!” So I was like, “You know what? Why don’t I just start doing those favorite bits?” So that’s what we did. We decided to do it outside, which helps our budget with lighting and everything. And we show different neighborhoods that people can recognize. The first season wasn’t quite as diverse with the backgrounds, but the second season is going to be all over town. So I get to showcase some of my writing—I don’t like being in front of the camera—and we get to showcase a lot of Philadelphia talent, on both sides of the camera. [We have a] really talented cast and crew. And now the fun is just kind of seeing how Philly reacts to this now and seeing how Philly connects with this project. I want it to be very Philly-centric but at the same time, very universal. You can be watching this in LA, and you don’t have to know this is Philly—we don’t make jokes about cheesesteaks—but at the same time, it’s very connected to Philly.

Season 2 of ‘My Ruined Life’ premieres on Sunday, November 18th at www.myruinedlife.com, after which they will take a break for the holidays and resume a weekly release schedule in January.

Matt Aukamp is a writer, performer, and occasional improviser (The Win Show). You can usually find him bothering the world on Twitter at @mattaukamp.