The Company You Keep star Milo Ventimiglia breaks down that twisty premiere

Warning: This article contains plot details from the series premiere of The Company You Keep.

He's a criminal. She's CIA. And together they're... stumbling into a relationship. Or danger. Looks like both.

Sunday night's premiere of The Company You Keep welcomed Milo Ventimiglia back to network television (though this time on ABC), back to family drama (though a different and more dangerous kind), and back to romance (what we said in the previous parenthetical). Let it be known, though, that while his new character, Charlie Nicoletti, boasts a big heart like This Is Us patriarch par excellence Jack Pearson, they share little else in common. Charlie is a highly skilled con artist whose mother (Fran, played by Polly Draper), father (Leo, William Fichtner), and sister (Birdie, Sarah Wayne Callies) are also grifters who conspire together in this illicit family business. In addition, Charlie's pursuit of Emma (Catherine Haena Kim), who, unbeknownst to him is an undercover CIA agent, is about to thoroughly complicate his (way of) life.

So, boy meets girl at hotel bar. Boy and girl drink too much. Boy and girl bond by telling each other fun lies (he's a yoga instructor; she's a pageant queen-turned-rocket scientist) before jokingly-not-jokingly telling one truth ("I'm a criminal"; "I'm CIA") and winding up in boy's hotel room for the weekend. Later, by chance, Charlie runs into Emma at a black-tie D.C. function; she's there with her politically connected family, while the Nicolettis are running a con on a corrupt televangelist played by guest-star Doug Savant. (Context: the Nicoletti family only targets "deserving" people, and this mission is happening only because, earlier in the episode, they ripped off $10 million from Irish mobster Patrick Maguire on a fake warehouse deal, but immediately lost that payday when Charlie's fiancée, Tina, disappeared with the money.) Sparks once again fly between Charlie and Emma, but after Birdie pulls her brother aside and reminds him to keep his head in the con game (see: Tina), he abruptly calls it off with a disappointed Emma.

Emma has other pressing things to worry about, though. She's been tracking an illegal global fentanyl ring that's coming to America, and a breakthrough in the case via surveillance-camera footage put a face on the operation: Patrick Maguire (Timothy V. Murphy), and lucky for Charlie, just the back of his own head. Emma and the FBI wait at an airport to arrest Patrick, but the feds pull the (metaphorical, not literal) trigger too quickly, allowing his right-hand woman, Daphne (Felisha Terrell), to escape in a car chase that injures Emma.

While Emma nurses her (metaphorical and literal) wounds the next day, Charlie pops up at her door with an apology and a few words of caution/explanation. "The more you know about me," he says, "the faster you'll want to run." She throws caution/explanation to the wind and plants a kiss on him, and the two decide to get lost in each other's company again. Of course, fantasy can only keep reality at bay for so long. When Charlie returns to his family, he finds Daphne and her goons waiting. She demands a rapid repayment of the $10 million, plus another $5 million in interest. She warns Charlie: "You're not going to be able to lie your way out of this one."

Where will the Nicolettis find $15 million fast? How will Charlie and Emma find love in the midst of lies? And what even is a relationship these days, anyway? Always respecting the orange, EW put down the theramin, cranked up the Stones, ordered a negroni, and asked Ventimiglia to answer a few burning questions about the company he's now keeping.

Eric McCandless/ABC Catherine Haena Kim as Emma and Milo Ventimiglia as Charlie in 'The Company You Keep'

ENTERTAINMENT WEEKLY: What did these two crazy kids just get themselves into?

MILO VENTIMIGLIA: A whole lot of trouble. [Laughs.] Off the pilot, finding both Charlie and Emma in a place where they're heading full into something [where] they're not completely aware entirely of the big picture — they're heading for trouble. But then beyond that, their professional lives — those also look like they're going to have quite a bit of excitement, too.

Charlie gives up on Emma at the black-tie function, but after talking to his parents at the bar, he goes after her and shows up at her house. When he returns to the bar at the end of the episode, everything has changed, given Daphne and the $15 million bill. How will this turn of events impact how he approaches his relationship with Emma? And is this a wise idea if he's got to stay in the game now?

I mean, not a very comforting place for Charlie to be knowing what he's up against. But at the same time, he battles with how his professional life will impact his personal life, pretty much from the jump of this season, leading past the pilot episode.

How big of a game changer is Daphne — and how many wrenches will she throw into both of their lives?

First of all, I gotta say, Daphne's calm is probably a welcome thing for Charlie, but her presence and threat of potential violence toward him or his family is unnerving. Charlie is stuck in a place where he has to do what it is he can to get out from underneath the Maguire clan. But at the same time, the fact that they're not all entirely dead in the beginning? That's a good thing.

Any hints on how Charlie will make $15 million very fast?

[deadpan] I mean, knowing that they made $10 million in the first two minutes, I think $15 million shouldn't be too difficult to pull off…. No, it's a large number. It's a terrifying number. It's something that isn't to be taken lightly. But what we're wanting to do over the next several episodes is show the smarts of the Nicoletti family, how Charlie is leading them out of this trouble he put them in and [how] they're getting back to a place that's maybe a little more digestible than being underneath the Irish mob.

In that first scene in the bar where Charlie and Emma meet, they're lying to each other about their jobs before she challenges him to say something true. They tell the truth to each other, couched as a joke. In some small way, does that let them rationalize to themselves, "Well, technically I did sorta confess the truth at one point"?

I think there is zero rationalization in that truth. I think both of them are worried about their professional lives impacting their personal lives. The admission of her being a CIA officer and him being a criminal — that's something that comes up between Birdie and Charlie quite a bit, this honesty with their partners and how even Birdie's ex understood what the family business was. But much like Charlie and Tina, Tina was in on it in the first place. So Charlie thinking that Emma just works at a logistics firm and she comes from this political dynasty family — there's of course complication to how she would accept dating a criminal. But at the same time, who says she wouldn't be okay with it? But when it's discovered that she's a CIA officer before it's discovered that he's a criminal, I think that complicates things further.

The night they meet, after he says goodbye in the bar, she shows up at his hotel room door and they start to kiss. You think it's going to be the the big, hot sex scene, but expectations are subverted as it turns into the big, hot unstructured burger scene: He stops kissing her and asks, "Are you hungry?" and she says, "I'm starving," and they devour the food and pass out. What was your first reaction when you read that scene?

That was some real honesty, you know? Think about what the two of them went through in the beginning of the day in their individual lives. And at that moment, to be pretty honest about it, I thought it was a good take…. [Some of that scene] is myself and Ben Younger, our director, and Catherine Haena Kim just kind of riffing on a lot of that. The unstructured burger and "the seven years of bad sex" — that was all just kind of improv and thrown on the fly.

Aside from the secret that they're hiding from each other, what's the biggest challenge facing this couple? Is it how their families might react? Or their own trust and vulnerability issues?

I think it's all of it. When you're getting into something new and you're excited about something, you're trying to give that person your best version. But everything that brought you to that moment comes along with it. So you have to accept that both of them have things that are going to hang them up. I really think that it will happen with Charlie and Emma, and hopefully they can see beyond it, learn from it, where sometimes it actually doesn't work. Sometimes it can break a relationship.

Whose family will pose a bigger obstacle for this budding relationship?

I think the Nicolettis are pretty forgiving. Just given who they are, they ask a lot of questions, and I think they have some doubt, but at the end of the day, when they are accepting of someone, they go full in. The Hills strike me as a little tougher. The Hills strike me as a family that expects a little bit more because of the polish and pomp that is needed in the D.C. political circuit.

What intrigued you most about the Nicoletti family dynamic? There's the race against the clock given Leo's dementia. There's the idea that Charlie and Birdie were brought into the family con business at any early age, and the conflicting feelings of obligations and resentments and loyalties they feel…

I want to say it's the blind trust, but I think it's knowing that they truly are looking out for one another. Leo with his speech to Charlie, where he's like, "Either we're all out or we're all in" — that right there sums them up. They're not bailing on each other; they're not turning on each other. Even though they are in these situations throughout the course of the show, at the end of the day, they're there for one another. The family itself is solid, which is just a reassuring thing. You have the stresses in your own personal life, as Leo does, as Charlie does, as Birdie does, as Fran does, but at the end of the day, everybody's really truly there. They're not going anywhere.

Charlie and Emma are hiding huge truths, and we know the truth always comes out eventually. Could the chickens come home to roost here maybe a little sooner than one might think?

I think it's going to come a lot faster than people expect it would.

And in a way viewers won't expect?

Yeah. I mean, the discovery of who they are individually, professionally. Emma's reveal is sooner than Charlie's, but when Charlie's arises, it's no less impactful.

What was the biggest challenge in filming this first episode?

Honestly, it was the entirety of it. It was knowing that this was, personally, the follow-up to This is Us. It was a new character, it was a new cast, it was a new setting. I don't think there was one scene that was challenging more than the next, but I think it was a collection of, "Hey, we gotta do this good. We gotta do this right. And you know what? If we're having fun while doing it, which we did, I think that'll show through." [Ventimiglia spoke previously with EW about wanting to find an "unJack" role after This Is Us, which can you read here.]

Have we seen the last of Charlie's fiancée, who swindled Charlie and his family at the warehouse?

[Laughs.] It's one of the biggest questions I get. For the moment, she's made off with the money. At some point, down the road in the lexicon of The Company You Keep, I'm sure Tina [Bridget Regan] will return.

What can you tease about the second episode, which features Charlie and Emma in, let's say, a different kind of hotel room intrigue? [See video above.]

It's definitely edge-of-your-seat watching, knowing that both of them are on the job and might have a run-in professionally before they even know who they really are — the criminal and the CIA officer. What else can I say about it? We dive more into the fun of the Nicoletti con world. We start to understand the code of the Nicoletti family, that they aren't just going after anybody but they're going after people who are deserving of the attention. And the planning it takes, the strategy it takes. It comes together in a 42-minute episode, but at the same time it takes a lot from this family to come up with a strategy to get what it is that they're wanting. And at this point, getting out from underneath Daphne and the Maguire clan and that $15 million bill.

Finally, what is the best con job that you've ever pulled in your own life?

Sticking around Hollywood as long as I have? [Laughs.] No, seriously, it's funny, being on a press tour and the more I'm outside of production [the more I'm] talking about how the world of grifting is strangely no different than acting. You're putting on a different character and you're getting an emotion out of somebody, looking to get something in return. But what I'm looking for as a performer is an emotional response to what it is that I'm doing. I'm using all the tools in my bag to make sure that people are enjoying the show. So when anybody tells me, "Hey, I really liked it. It was fun," that's exactly what I want people to have with this show. So, acting, conning — it's kind of all the same right now.

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