‘It Was Just Very Stupid And Silly:’ Jessica Williams Shared The Story Behind Improvising With Damon Wayans Jr. On The First Shrinking Scene They Shot Together

Spoilers for Shrinking Season 2, Episode 4 are ahead! If you aren’t caught up, you can stream the comedy with an Apple TV+ subscription.

Shrinking’s cast was already stacked. I mean, it’s led by Jason Segel, Harrison Ford, Jessica Williams and Christa Miller. However, it got even better when the fourth episode of Season 2 dropped on the 2024 TV schedule, and Damon Wayans Jr. showed up as Derek’s co-worker and Gaby’s new love interest, Derrick #2. So, when I had the chance to chat with Williams about this new character, she gushed about collaborating with the Poppa's House star and shared the hilarious story behind the first scene they shot together.

Conveniently, right after Gaby said “I want a Derek” as a compliment to Liz’s husband, he introduces her to Derrick #2, his old co-worker who is played by Wayans. Then, a few scenes later, Gaby is clearing out her stuff from Jimmy’s house now that their fling is over, and she runs into him again. That flirty little moment outside her friend’s house was not only adorable, but it was the first scene Williams shot with the New Girl actor, as she explained to CinemaBlend:

Damon had to come in really quickly, I think. He signed on maybe, like, two days before he started another job, so we just kind of had to feel out each other, especially in I think Episode 4 is our first time working together.

The Incredible Jessica James actress went on to say that even though they didn’t have much time to prepare, they found their groove quickly. She said that first scene where Derrick holds her box of stuff was how they discovered “each other’s rhythm and sense of humor.”

It’s also what led them to the hilarious as well as “lewd and crude” vibrator jokes, as Williams explained:

But we -- I think the first scene, Gaby's clearing out a box of dildos and vibrators from Jimmy's house that they had -- maybe [it's] the second scene. And we got really sort of lewd and crude…there was one [take] where we were talking, and I don't know if it made it in, where it's like, ‘Oh yeah, that's the big red vibrator.’ And then my character goes, ‘I call it Clifford.’ And then he goes, ‘Oh, because the Big Red Dog.’ And then I think he, like, barks, he’s like [barks].

After that, the actress told me that moment felt “classic” to her as she and Wayans worked out the hilarious scene together. It truly was wonderful, and it helped immediately establish Gaby and Derrick’s shared sense of humor and their chemistry.

Continuing to tell the story behind this moment, Williams said she wasn’t sure if that joke made it into the final cut of the show. I assured her it did, and she got excited as she explained:

Oh, great. Thank you, Bill Lawrence. Great. Well, I'm happy that made it in the show. But that was one of my favorite things, because that was like our first joke exchange where we were just building on top of each other, and it was just very stupid and silly.

As the episode went on, we got more really cute “stupid and silly” moments – like Derrick hearing Gaby’s trap remix of the Lord of the Rings score – as the two characters sweetly began their relationship, and I can’t wait for more. Seeing new relationships flourish in meaningful ways via funny interactions is one of the reasons why I think Shrinking is one of Apple TV+’s best shows. And it’s clear to me that Williams and Wayans have the perfect chemistry to keep that silly goofy and sweet energy alive.

To see how this lovely relationship evolves past this meet cute that involved a funny vibrator joke, you can stream new episodes of Shrinking every Wednesday on Apple TV+.

Riley Utley
Weekend Editor

Riley Utley is the Weekend Editor at CinemaBlend. She has written for national publications as well as daily and alt-weekly newspapers in Spokane, Washington, Syracuse, New York and Charleston, South Carolina. She graduated with her master’s degree in arts journalism and communications from the Newhouse School at Syracuse University. Since joining the CB team she has covered numerous TV shows and movies -- including her personal favorite shows Ted Lasso and The Marvelous Mrs. Maisel. She also has followed and consistently written about everything from Taylor Swift to Fire Country, and she's enjoyed every second of it.