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Jessica Williams on Her ‘Shrinking’ Season 2 Relationships

[This story contains spoilers from the first half of Shrinking season two.]

The first half of Shrinking season two has already been a rollercoaster for many of its characters.

The introduction of Brett Goldstein’s Louis, the man who killed Jimmy’s (Jason Segel) wife and Alice’s (Lukita Maxwell) mom Tia (Lilan Bowden), throws the core father-daughter duo for a loop. Gaby (Jessica Williams) has to start caring for her mother (Vernee Johnson) and get out of her casual sexual relationship with Jimmy. Meanwhile, Liz (Christa Miller) is falling apart, and no one seems to notice.

But it’s not all bleak. Brian (Michael Urie) and Charlie (Devin Kawaoka) are adopting a baby. Sean (Luke Tennie) is making some real strides in his mental health progress (despite a few missteps). And there’s a new love interest in Gaby’s future thanks to Derek (Ted McGinley) introducing her to Derrick #2, played by none other than Damon Wayans Jr.

For Williams, getting to explore a relationship with Wayans’ Derrick was interesting because Gaby is now in a healthier situation than she was with Jimmy at the beginning of Shrinking season two, but she’s not as into it. “We get to see Gaby reflect, and she’s toxic, and the ways in which she does that, and the ways that you can work through it, and the ways that you can choose to figure it out or not,” the Emmy nominee tells The Hollywood Reporter. “Who you choose to date and who you fall in love with, it makes you confront aspects of yourself that you wouldn’t be able to if you were just alone.”

The Love Life actress also notes that she enjoyed being able to dive deeper into Gaby’s family life with her mother and sister, portrayed by Johnson and Courtney Taylor, respectively.

“They’re really amazing actresses, and there’s something really cool about being able to see where Gaby comes from,” she says. “That story about that part of adulting and getting older, where you have to figure out how to take care of your parents when they get older, is something that we all have to — hopefully, if your parents are still alive — deal with later in life and figure out.”

In the chat with THR below, Williams also opens up about her onscreen dynamics with Segel and Harrison Ford, Gaby’s friendship with McGinley’s Derek and Miller’s Liz, and her hope to share scenes with Goldstein in season three.

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What was it like returning to the role of Gaby after being nominated for an Emmy for the first season?

It was really cool. The day that they announced the nominations, I think at midnight, our union, SAG, was going on strike. So, that was a really surreal experience, but I also wanted to support my union. So I had maybe a day to celebrate — 12 or 15 hours, like everybody else. And then at midnight, it was like, “All right, let’s strike.” When the strike happened, we were a few weeks away from starting filming on season two, so we got pushed back by like six months. I had a lot of time to not work and sit and think about the character, and I had built up this pressure in my head, especially after getting the nomination. “I don’t know if I can do this again. I don’t know if I remember.” I’ve never had a character that I’ve gotten to return to, in general. Everything’s been a limited series or The Daily Show, which is its own beast. So I was really nervous. I remember being really scared and just being like, “Oh shit. What if it was a fluke? What if I don’t remember? What if I can’t do that again?” That was the biggest thing.

And then once you got back onto set and were ready to start up again, did it all come back?

Yeah, really, once I got in the clothes and got on set, and feeling like being back in the office again. It came back to me really quickly, but I remember being so nervous and texting the rest of the cast, “Dude, I don’t know if I can do this. Am I gonna do it again? Because people really like Gaby.” But I got used to it really quickly. And then some weird things happen, where I was more sure of who Gaby was.

In the first season, I don’t know if you know this, but Bill [Lawrence] and Brett [Goldstein] and Jason [Segel, the creators] were all like, “Whoever we cast as Gaby, we want to tailor the character to her.” So the first season was really us figuring out who she was and feeling our way through. The second season, I was like, “Oh, am I really bad at my job, kind of phony?” And it was like, “No, you guys created a character, and now you understand the beats of her character. So you just get to kind of enjoy that, because you worked really hard trying to figure it out in the first season.”

You and Jason Segel have an incredible dynamic onscreen. How did you create that?

I remember our initial meeting, a Zoom call where I met Jason and Bill and Neil [Goldman], who’s our head writer, and that Zoom call was, like an hour. For half of it, I think we were just all talking about basketball. I live on the East side, and he does too. I got off that Zoom call, and I was like, “Well, you know, I wish them luck. I like all those guys, and I hope whatever happens to the show, it goes really well.” But we all just had a really good chemistry. And with Jason, it was just effortless. I think we seem really different, but there’s this weird understanding that the moment we met, I was just like, “Oh, you’re weird and I’m weird, but I get it.” So, it was just really easy. He’s the easiest person to shoot with. There’s so many good combos that we have on the show. But whenever it’s with him, there’s nothing I have to do. I just get to sit back, relax and enjoy watching him work, which is one of my favorite things about this job.

You also have a great dynamic with Harrison Ford. I love how your characters have a deeper relationship this season, where he looks to Gaby for a lot in his life, and she’s driving him to work. What was it like working opposite him more this season?

Amazing. I signed on to this show not knowing that they had secretly gone out to Harrison Ford, and I just kind of banked on working with Bill and Jason and Brett, which I was really excited about. Then, a week later, I found out Harrison Ford had agreed to do it, and I was like, “You guys are fucking joking, right? Like, this comedy? This half-hour comedy? Sick.” Once it was very real, I was like, “This is insane.” But what’s nice about how Gaby and Paul’s (Ford) relationship has developed over time is that Gaby has this reverential sort of feeling — and Jimmy, too — towards Paul, and he’s really good at his job. I think there are a lot of traits that Gaby really admires and sees him as somewhat of a distant father figure. I think he sees her as a distant daughter figure, and I think he sees it with Jimmy, too. He’s a distant son, and that’s really nice to work with Harrison Ford in that regard.

Then, the other thing about Gaby is that she’s kind of not afraid to say what she’s thinking, if it’s not something that has to do with her mom or her really personal relationships. So it’s really nice to be able to talk to Harrison Ford about safe dick. And I think the writers have a lot of fun seeing that. I mean, I never thought that on the timeline of Harrison’s career, there’s this little blip on there where I get to talk to him about safe dick, and he repeats it back. There’s a scene in this season, where he’s talking to Sean, played by Luke Tennie, and to Liz, played by Christa Miller, where he’s like, “You want me to pull my pants down and clap my cheeks and make my ass clap?” What a funny thing to be able to enjoy him in this kind of really different character for him. It’s really great. I’m really blessed. I feel like I did everything right to get to this point, to be able to do that with him. It’s a dream.

At the beginning of the season, we see Gaby struggling with her feelings for Jimmy, and how they’ve sort of entered this relationship where it’s casual for him but not for her. Why do you think they were bound to get to that point eventually?

I think that happens a lot when people are grieving, actually, and nobody talks about it. If you have the best friend, and you have the partner of the person, or the ex, and they have this huge gaping crater in between them. There’s this huge shared trauma and this shared bonding and this shared relationship. I think they’re gonna jump in that caterhole and maybe fuck each other. That feels like it’s a form of grief and grieving, and I think with the confusion and Jimmy not knowing where he’s at and, and even the danger that comes with friends with benefits. For some people, that works really well. There’s no set rule, but I think for Gaby, who’s a really feeling person, it’s really hard for her to have sex and not feel this emotional connection. And I think that’s just the kind of woman she is. I think they both explore their feelings for other people in this season, and that’s something that’s really exciting and good for them.

Gaby also has a really beautiful friendship with Liz, which this season starts to extend to Derek as well. What was it like playing out these scenes with Christa Miller and Ted McGinley?

I love Christa and Ted. Christa is married to Bill [Lawrence] and, aside from being a great actress, she’s also Bill’s wife. Bill thinks it’s really funny to see this odd pairing, and so he’s pretty obsessed with it. So he’s always like making it happen, which is a joy. They write Liz to Christa, and I feel like it’s really fun that both of our characters are written towards us, and we get to have this really silly dynamic. And then, just to add to Derek, Ted McGinley is just a really special actor. On set, he’s like this kid that you’re in the back of the classroom with giggling, and he’s really fun to be around because he’s always being sneaky and being quote-unquote bad. But he’s always got this point in his eye that you can see with Derek, where he has this amazing ability to act but then on top of that, just yell, “Eat a dick, Pam!” and that’s that feeling of being back in the back of the class, and he just has that part of his personality. And so he’s a real joy to work with. I’m really excited that he’s a series regular.

It’s funny, because every time they ask me about the show, I could say each character is the heart of the show. It’s like, “No, Alice is the real heart of the show.” “No, Derek’s the real heart of the show.” It’s really great to be able to do that. I also love being friends with couples. I have a few couples that I’m really good friends with, where I love the both of them very much, and they both come over and hang out with me, and then sometimes I’ll hang out with one, and I will hang out with the other, and it’s like a really nice, modern, sort of 2024 take on friendships. I think there’s this old-school idea that people can’t be friends with husbands and wives. I don’t know it feels like a weird thing. I don’t know how to explain it, but it’s this weird, taboo thing. And I love that Gaby is in this really fun relationship with the two of them, and they all kind of take care of each other. It’s really awesome.

Derek also has this really sweet moment with Gaby where he tells her that she’s always taking care of other people and to let someone take care of you. Why do you think that was so important for her to hear from him?

If anybody knows about Jimmy and Gaby’s relationship more than Jimmy and Gaby, it’s Derek. He’s had a total bird’s eye view from his balcony of everything. He really hears everything. Even when he hears Jimmy talk to Alice, he’s like, “Dude, you blew it.” He sees everything, that’s the implication. So it’s really nice that he’s supporting Gaby because he really saw their relationship come together and fall apart, and sometimes it’s nice when you get advice from people that you least expect. I think Derek comes through for a lot of people this season. He gives really great advice to Brian (Urie). He gives really good advice to Harrison Ford. He’s just really good at advice, and if anything, he should be everyone’s therapist, rather than the three people they choose to be therapists on the show.

Except for, it seems, Liz, who he struggles to be a therapist for.

That’s right. I mean, everyone’s got their own problems. Even someone who seems like they’re OK, and they’re kind of floating above water, they have their own issues. That’s something that’s really nice about our show. Every character is so great that we and the writers can choose to go in and out of their lives as much as possible in their inner worlds. It’s really great because we just have a great foundation.

Derek also introduces Gaby to her own personal Derrick, played by Damon Wayans Jr. What was it like sharing these scenes with him, and what can you tease about what’s to come for Gaby and Derrick #2 in the back half of the season?

Gaby’s in this relationship where Derrick #2 is technically healthy and technically healthier than her. Online, we always talk about cutting off people that are red flags, and it’s like, “What if you’re the red flag?” It’s kind of toxic to just point out when everyone else is toxic, but there’s no way you’re walking through not leaking a little toxicity from survived trauma, or the way you’ve learned to adapt in the world. So, we get to see Gaby reflect and she’s toxic, and the ways in which she does that, and the ways that you can work through it, and the ways that you can choose to figure it out or not. Falling in love and liking someone, it’s like a mirror. It’s the most immediate mirror you can get. Your pet’s a mirror to an extent, because what you put into your pet is kind of what you get out, but they’re not another living, breathing human. Then, I think even more so, who you choose to date and who you fall in love with, it makes you confront aspects of yourself that you wouldn’t be able to if you were just alone.

This season, we also get to see some more insight into Gaby’s relationship with her family. What was it like exploring that?

Vernee [Johnson] and Courtney [Taylor], they play my mom and my sister, [respectively], they’re really amazing actresses, and there’s something really cool about being able to see where Gaby comes from. Also, I think that story about that part of adulting and getting older, where you have to figure out how to take care of your parents when they get older, is something that we all kind of have to — hopefully, if your parents are still alive — deal with later in life and figure out. So, it’s really interesting to experience like that through Gaby of this dynamic of figuring out how to take care of someone that you love. I think it happens quite a bit, so it’s great. They’re just amazing actors, and they’re really funny, so it was just a joy to work with them. I really hope that that comes through on the show. Our crew is amazing. Our writers are amazing. Our directors are amazing. It’s a really joyful set, where we all just really enjoy each other, and therapy is always the topic. So everyone’s into, for the most part, reflecting, and we have fun making it. So I hope it comes through.

We see Liz calling Gaby out on making her sister continue to be her mother’s caretaker because of all her struggles with addiction as a child. Talk to me about that scene.

I think Gaby tends to have issues with being co-dependent and of being a martyr. She inserts herself in other people’s problems so that she doesn’t have to focus on her own. And I think sometimes having a really good friend — and a good relationship with anyone — is not somebody that just yeses you. It’s someone that also is going to tell you your blind spots, if you’re open to it, and tell you in the most gentle and loving way, from a place of love, like, “Hey, this is a pattern I’m noticing.”

There’s something really nice about Gaby and Liz’s love for each other. They love each other enough to trust that the person’s comments on their lives, sometimes, if it’s rude or not, it comes out the wrong way, it’s not an indictment of their character. It’s more like someone who loves you, telling you about yourself. That feels different than someone who doesn’t like you or love you, saying things because then it’s mean. But I think it really speaks to the solidness and the love that Gaby and Liz have for each other. It’s a really special dynamic on the show because not a lot of people tell Gaby about her shit. I feel like she’s always talking shit about everybody else to everybody else, but nobody really calls her out, so it’s always nice if she gets called out.

We also see Jimmy finally put his friendship with Gaby first and be there for her, without having the ulterior motive of sex (even though he wore his sex underwear by mistake). Why do you think it was important for Jimmy to come through for Gaby in that way?

It’s just good for friends to come through for each other. I think it’s really important to show male and female dynamics onscreen where guys are just showing up for women, without the want for sex, without an ulterior motive. Especially in this day and age, it’s more important now than ever, to show white guys showing up for Black women as friends. It’s trying to show modern relationships. I love when my guy friends show up for me, and I love to show up for them. I love to show up for them and their partners when they get in relationships and love on their partners too. It’s just about having relationships in 2025 and 2024. Love is like having no ulterior motive. It’s simply showing up for the other person, without needing something in return. That was really important for their relationship, and for him to help start mending the damage that they both had created.

Bill has talked about this season being all about forgiveness, and we see that with the introduction of Brett Goldstein‘s character, Louis. What did you think when you first read that his character was coming into the season in the script?

I was really excited. I was really excited for Lukita Maxwell, the actress who plays Alice, and for Jason Segel. That guy left a crater in their family. I wanted scenes with Brett. I don’t think I have any, and I wanted to know about their relationship. I didn’t get to do that this season, but I think Brett does really beautiful work, and so does Lukita, especially with Brett, and Jason too. I think they’re just in a jam. It’s one of those things that, as someone who’s on the show, I’m like, “Fuck, I want to watch the show.” I read the script. I’m like, “I want to see that play out.” And I think the writers and Bill wrote really, really beautiful stuff.

Some of the best stuff this season is stuff with Brett. I feel like he just has that sort of ability that everything that he’s on, whether he’s guest starring or he’s jumping onstage, he just makes everything better. You’re like, “Oh, you elevate and make everything better,” just by being himself and talented. So I was really excited, and I hope that I get to find out how Gaby would feel about meeting someone who killed her best friend.

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Shrinking season two releases new episodes Wednesdays on Apple TV+.

Source: Hollywoodreporter

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