Milana Vayntrub Opens Up About What It's Like to Star in an Interactive TV Show

Milana Vayntrub is probably best known as the amazingly quirky and oh-so-lovable Lily from those AT&T commercials, though you've also probably caught her as Sloane Sandburg in This Is Us or when she guest starred as Gilfoyle's girlfriend Tara in Silicon Valley. This year, however, she plays the lead role in That Moment When, a completely innovative and fascinating interactive TV show from streaming site Eko. "Jill is a hot mess. It's up to YOU to navigate through a series of awkward moments that either leave her somewhat dignified or even hot-messier," the series description reads, but what's amazing about the series is that it really is up to you to choose what happens — it's the very first of its kind to offer viewers the chance to decide what happens to the characters on the screen.

Vayntrub's Jill is, as advertised, a hot mess. But she's one hell of a relatable mess, and by the time you've chosen your own adventure throughout the series, it starts to feel like she's someone you know in real life — and that's a definite indicator of just how wonderful an actress she truly is. I spoke with Vayntrub by phone in early December to talk about her role in the show and the groundbreaking technology that drives the series from beginning to end.

POPSUGAR: How would you describe Eko as a platform?
Milana Vayntrub: Eko is an interactive platform, so they make shows that you can play. [laughter] Our show is a sitcom where you get to choose if a character marries the guy or breaks up with the guy. I mean, maybe not those exact examples, but you get to take initiative in the lives of your favorite characters.

POPSUGAR: And how did you first get involved with it?
MV: Sandeep [Parikh], who created the show, is one of my best friends. We used to be roommates. We perform together. So he's definitely one of my creative soulmates, and when he asked me, I was like, "Yeah, I would do anything that you wanted to do."

POPSUGAR: Tell me, in your own words, what That Moment When is.
MV: First of all, I'd say insane comedy. And insane because the situations are totally grounded and real. They're going to a party and not remembering somebody's name, or getting dumped at a restaurant (which has happened to me), or asking their parents for money. And then, ultimately, the whole thing leads to this big high school reunion, which is also something that we've all had to deal with or opted out of dealing with. I think if Jill was a little bit smarter, she probably would have also opted out because she was definitely setting herself up for disaster. But sometimes we learn the most from the most disastrous situation. So that was definitely Jill's calling. But ultimately, Jill's character — I think that she's somewhat of a version of me. She's maybe a little braver and a little louder, but I think the thing that makes her relatable is that she's in all of these situations that we've been in. She's not always the best person; she gets lonely and leans to the selfish. And I think that's what makes her appealing, because she's someone we all know.

There's one situation in the roommate episode where, if you play it a certain way — sidebar: that's also the most fun part of the show, that you can play it a different way and get a different set of jokes and situations every time — but in this one, the roommate character asks her if she thinks she's pretty, and because Jill can't lie, she just kind of nods uncomfortably . . . and I love that. I love that Jill is so blatantly obvious, and it's interesting to be on the side of Jill because you know when she's manipulating and you know what her tactics are, and it's kind of situations that you — like me, as a person, I would not be brave enough to explore, but it's nice doing it through this platform where everything is really playful, truly.

POPSUGAR: How much of what happens in the show is scripted and how much is improv? It's all so tight, it's hard to tell.
MV: Most of it is scripted, and then we improvise on top. There's always a script — and it was always stellar and totally carried itself — but because Sandeep and I are both improvisers and I have a problem where I can't not improvise, they cast other improvisers in the show so there were also a bunch of extra lines, too. But it doesn't feel like a mumblecore movie where it feels really improvised because they only have a loose outline. We had a much tighter script, and then we more improvised jokes rather than scenarios or full character pieces.

Finding and hiring improvisers was key, though. When you have people who are actively creating their own content, they know the dimensions to which they can improvise. They know when you've added so much content that now it's not editable. Knowing your outs and understanding, for example, not talking over other actors — that's a very basic improv tool that you get through practice, and you get also through watching and making your own stuff. Because a lot of the actors were also writers and creators, it was mostly really seamless to kind of support other people's jokes or to set them up. Also, I can't give enough credit to the editor, because that's really what makes improv work.

POPSUGAR: Do you feel like you created another level to Jill's character by doing improv on top of the script?
MV: I think I get closer to these characters when I can improvise. As an actor, you don't step into other people's words, but you get to add your own words, so you need to speak as a person because it gives the role character. It does become easier to understand them or to imagine over time. Especially when it worked. When the writers or the director laughs at your improv, that's just a sign to me as the actor that I'm hitting on the notes that they want for that character. That's the goal that I have. I like adding the improv because I'm also adding more to the project. I feel like I'm contributing and carrying my weight.

POPSUGAR: There are so many paths in the show. Did you have scripts for each and every potential path? Or was it all written and shot in pieces?
MV: For every six-minute episode, there's about 30 pages of script. It's usually there's a page per minute. So there's about 30 minutes of content for every episode even though you only see six. We would shoot multiple setups and different lines and different opportunities every time. And that's also a huge credit to our producer and director, who were able to organize all of those shots in their heads in ways that it's probably not easy.

POPSUGAR: Did you have favorite outcomes or did you just kind of approach it as completely separate scenes?
MV: You know when you are planning an important meeting or you're about to hang out with someone you want to impress? There are situations you play out in your head, if you're like, "If I get it this way, this might happen. If I get it this way, this might happen," and that's kind of — we got to play out all the situations. In a way, it was an acting exercise in not making a choice, which a lot of acting normally is figuring out what your character would do, and in this one, it's "Well, if this character could do it all." It's actually very freeing. But at the same time, I didn't fully understand how it comes together until the very end, and I'm so impressed with how it has, but now that I've seen it, I definitely have these routes that I hope people will take because I'd love to see — I want them to experience one take over another, but that's the past, man. [laughter]

POPSUGAR: Do you think you can experience the full story in just one viewing? Or do you need multiple variants?
MV: I hope that people watch it more than once and take entirely different experiences every time. Because all the jokes are worthwhile, and I think you'll also get to experience different sides of the characters depending on what choices you make, so I think it's worth it to go back more than once.

POPSUGAR: Which scene did you think was the most awkward scene you shot?
MV: There's a moment in episode seven where you have to dodge a creepy teacher from hitting on you at the reunion and that's — how many times have we tried to dodge an older man putting his hands on you when you don't want that? That is really relatable. In a way, I kind of hope there's a teaching moment there for the men that play, like, "Hey, this happens." You have to step into this woman's shoes and protect yourself from unwanted touching. It was an awkward thing to shoot, but also really professional, and then I got to have a conversation with that actor and we got to figure out where all of my boundaries are and where all of his boundaries are. That's not always what life is. But even when I play it now, I'm like, "Oh, f*ck, don't touch her. Don't touch her."

POPSUGAR: How would you compare the experience of doing the AT&T commercials to doing That Moment When?
MV: This was far more challenging because there's so many more lines. This was, like I said, 30 pages of dialogue a day — whereas the AT&T spots were one page of dialogue a day, and often, camera didn't have to move too much on the AT&T spot, so we kind of had a day of just shooting new 30-second spots in every different iteration. Like, I wish that in the AT&T spots, they showed all of the improvised versions that we came up with, but they're dead now and you'll never get to see that. The beauty of this is that you do get to explore all of the other improvised versions that we came up with. That's why movies have deleted scenes, and that's the beauty of digital reels that are dug up on the internet.

POPSUGAR: What did you like best about doing the show overall?
MV: One of the things that I think is really fun about this character, and something that I see coming up more in TV and film, is dynamic female characters who are not about being sexy and are not about being attractive or liked by men, and in fact, they may be downright unlikeable, just like human beings are in actuality, and I capitalize human beings. With shows like this, get to be this multidimensional mess of a human and experience this difficult and hilarious situation. So I'm really proud of how likable this — maybe not likable [laughter] but watchable — this otherwise mess of a person is. And we didn't ever have to worry about making her digestible. But, in fact, you get to play these situations for fun. Do you know what I mean? I think I kind of rambled there. It is totally liberating as an actor, and I think really fun to see as a viewer.