'The Circle': Jack Reacts to Catfishing as Emily and His Epic Makeup Challenge Fail (Exclusive)

The reality star opens up to ET about his hilarious 'Glammequin Challenge' gone wrong!

Jack is looking back at his time in The Circle, and what he wishes he could have done differently.

While speaking to ET via Zoom, the reality star opened up about what it was like catfishing as a 21-year-old girl named Emily for season 2 of the hit Netflix competition series.

"I was sort of up in the air on whether I wanted to catfish or not. I kind of just talked with my casting people and we were like, 'What would be the best method to get on the show? What would be the most entertaining thing?' And that’s how we settled on Emily," Jack recalled to ET's Ash Crossan. "By no means did I think being a sorority girl was my best chance to win, but I thought it was my best chance to get on."

As for his strategy, Jack said that it wasn't necessarily to climb his way to the top, but "to make sure with every single person in the game that I wasn’t one of their top targets."

"I definitely was not perfect, but I think when you’re looking at a game from a strategic shift standpoint, you try to look at it in a game theory sort of perspective; everybody’s operating in accordance with their best move," he explained. "And I'm a game player. I wanted to come in, crush it and kill it [as Emily]. This is something I've dreamed about for a long time. I wanted to win."

Jack aka "Emily" seemed to be well-perceived by his Circle peers at the beginning of the game, but everything went downhill for him in episode 7 when Queer Eye's Jonathan Van Ness introduced a "Glammequin Challenge" to the players. The contestants were asked to create a mannequin using items like wigs, glitter and makeup that were delivered to their door, a challenge Jack hilariously failed -- and that ultimately cost him the game.

After seeing Jack's work, the other players immediately became suspicious of "Emily" for not knowing how to apply makeup as a woman. Jack was put to the test again during a round of "Truth or Dare," where he struggled to name popular beauty brands.


"The makeup challenge, I think, was a hilarious moment. It was fun to watch, although kind of depressing," he said of watching it back on TV. "When they first said we’re doing a makeup challenge, I kind of knew. I was like, 'I don't know anything about makeup, so this could be really bad.' Y'all did not even see half of the struggle. It was horrible. I was painting ... it was like I was doing the third grade watercolors. I was getting one of the brushes, wetting it in the sink and dabbing it in the blush, or I don’t even know what it would be."

"There was actually moments where I thought I was doing OK, which probably made it even funnier," he added. "I definitely could have taken more notes on makeup brands and stuff like that. But I don't really know if I ever would have realized that I needed to practice makeup for hours to actually figure it out. So, I feel like I was a little bit doomed with that challenge."

Jack admitted that it kind of felt like "the kiss of death" when the results came back and he heard critiques from JVN.

"I knew that would be on me immediately, and I did cry a little bit," he recalled. "I was like, 'OK, this is definitely dropping my chances of winning maybe to three percent.' It just sucked. I obviously wanted to win, and play my best game."

Little did Jack know at the time, however, that his time in The Circle was far from over. After he and Lisa (who catfished as *NSYNC star Lance Bass) were eliminated during episode 8, they were paired together to continue playing as a character named John. They collectively decided to make John a 64-year-old married gay man with three kids from Morgantown, West Virginia, who is a full-time psychic and part-time Santa Claus.

"It was crazy! I do think Lisa and I have a very fun dynamic, and it was good to just be in a room with someone else," he told ET, of what it was like joining forces. "Not only did we have nine or so days until that blocking, but we also had a two-week quarantine before [filming for] the game even started. So, even watching it back, my favorite moment of the episode was when Lisa and I first get together because I feel like I could see my energy kind of change. Because before that, I was kind of going nuts in my own head."

Jack joked that it was also "a lot easier" to catfish as someone who is the same gender.

"John just came together in such a weird way where, when we were introduced to the profile, the only thing we had was his picture, and his occupation had to be psychic," he remembered. "Then they showed us some of his other photos in his private album where he was dressed up as Santa Claus. So we’re like, 'OK, if we have to share more photos, it’d be hilarious to share a Santa photo ... we were trying to make him as lovable as possible."


Lisa spoke similar sentiments in her own interview with ET, revealing that it was a blast to share a suite with Jack.

"We got along really well, and we had so much fun together," she shared. "He made me laugh all the time. I almost peed my pants on a daily basis."

Lisa revealed that she and Jack kept track of their "lies" about John by writing them down in notebooks.

"I think we did a really good job making him likable and having people open up to us," she said. "With John, we had so much fun. Because with Lance, he's an actual person ... he is Lance. So, I didn't want to make stuff up about him. John, this was just molding a whole character to the point where I was like, 'I want to be friends with John. I wish John was real.' We all did, I think."

To see how far Jack and Lisa make it as "John" in The Circle, don't miss the season finale, launching next Wednesday on Netflix. In the meantime, hear more from Lisa below: