How long has the idea to have a “what if” episode been in the works?

Isaac Aptaker: It’s been in the works for a really long time. We’ve always known that we wanted to explore the notion of what their lives would be like if Jack had stuck around. But we were also incredibly aware of that being a little bit of a familiar trope. A lot of shows and movies do an alternate reality [storyline], how lives would have looked different. So once we stumbled upon the reason for it in our present-day storylines, where it would play into Randall’s therapy, we got really excited. It felt like it had a reason to exist and could be really propulsive in moving our actual stories forward.

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It was so interesting to see Randall with an earring, with someone other than Beth. Then you have Kate with a different husband and two girls. How much did you discuss what this new Randall would look like?

Elizabeth Berger: I think we discussed it ad nauseam. I would say every single detail. Sterling had a lot of opinions. I think in both versions, even in the rose-colored version, we wanted to make sure there was a real logic to Randall’s thought process, that it isn’t just random but really thinking, “If I reconnected with William, then I would want to stay in town and I would meet Beth and it would all be able to go this way.” The same for the alternate version. We really wanted to really dig into what would make sense for that other sort of “worse” version of his life, down to the color of his suit, to the earring. These are all long, drawn-out conversations we had.

IA: But I think the worst version of his life, single Randall, is such a good dresser. He’s a much better dresser than real-life Randall. That all-green suit with the different tones, I think, is the coolest thing Sterling’s ever worn on the show. So maybe not everything was worse in his new life.

EB: That was very much based on Sterling’s [red carpet] fashion. We were looking at photos of him at different events and were like, “He looks really cool here! He should just have that in this alternative version.”

What were some of the suggestions Sterling wanted for this alternate Randall?

IA: He had a lot of thoughts about his look and how to make it different enough but not go overboard. He didn’t want it to feel like a cartoon where it wasn’t the same guy. He had strong opinions about the types of women [alternate Randall] would be dating, what his apartment would look like. It was really just making sure it all felt very different from the guy we know so it’s clear we’re in a different version of life, but also not a totally different person than we knew. That wouldn’t be realistic. So it was keeping it grounded but also distinct.