The Circle season 4 winner reveals the 'cringey' flirting you didn't see

·10 min read
The Circle season 4 winner reveals the 'cringey' flirting you didn't see

Warning: This article contains spoilers about the season 4 finale of The Circle.

Frank Grimsley won The Circle season 4 in more than one way.

Not only did he walk away from Netflix's social media reality competition series with the grand prize of $150,000 (more than any previous winner), he also dominated the game just by being himself. He never lied about who he was, faked any connections to make allies, or based any decisions on strategy. He just let his personality shine through his DMs and made genuine connections with his fellow players. Week after week, it worked, as he kept getting ranked at the top, and despite being a clear threat to win the game from the very first time when he became an Influencer, the other players still never targeted him. In a game that's gotten increasingly strategic with each passing season, Grimsley set out to prove that kindness and authenticity is still the best approach to win.

Below, Grimsley unpacks his winning season — and reveals the "cringey" flirt exchange that wasn't shown onscreen.

The Circle
The Circle

Tom Dymond/Netflix Frank Grimsley in 'The Circle' season 4

ENTERTAINMENT WEEKLY: Congratulations on winning The Circle!

FRANK GRIMSLEY: Thank you! Today has been a crazy day.

What are you planning on doing with the prize money?

Well, I owe a lot of people money, so I will be definitely paying some people back. [Laughs] I might do a little splurge here and there. I might get me a little vacation, a little bag, but really just trying to save and invest. I want to make this money work for me for the rest of my life, because I may not win $150,000 ever again.

What has it been like now that you're able to talk about winning after keeping it a secret for so long?

Oh my god, that's the best part! I feel like I've had a baby. When the show came out, I felt like I was pregnant, but I felt different from everybody else, because I actually had another secret on top of me being on the show. It feels so surreal and euphoric. I'm just excited about the fact that people followed my story and got invested in my story, but then to see that I was able to pull off the win, even after being on top so many weeks, by simply just being myself, no major strategy — my strategy was being myself — I think that's the most exciting part, seeing people react to the nice guy finishing first.

That was really shocking and amazing to see, because every week when you continued to be ranked so high I was like, "There's no way that the other players are going to keep ranking him high. That's just not good strategy." But somehow strategy didn't come into play and you just kept on dominating.

Yeah! I mean, as someone that watches The Circle as well, even when I got Influencer first, I told everybody that knew I was going to the game, "I don't want to be Influencer first. I don't want a target on my back." Then I got in there and got Influencer first, and I'm like, "F---, I'm already messing up." But you know, God covered me every step of the way. I'm so grateful.

Take me back to the start of the season. How were you feeling about your chances to win, especially after you did get Influencer first?

Honestly, I really felt that I could win. I knew once I got on the plane [going there] that I was going to bring it back home. My best friend looked at me when he was driving me out to the airport, he was like, "Don't come back if you don't win." Here's the thing: I quit my job to go. My grandfather passed, as I revealed in the game, right before I came in, so I didn't get a chance to go home to his funeral, so I lost a lot. My account was in the negative when I left. My best friend paid my bills for me while I was gone. I knew that if I did not win, I didn't have anything to come back to, and I had already risked so much and lost so much so I think I just kind of knew. Everybody I came into contact with, I was like, "I'm going to win this," and they would look at me like I was crazy, and I was like, "No. I know everybody says this, but I promise you, the next time you see me, I'm going to win." I manifested it.

As you kept on getting ranked at the top, did that that give you the confidence you needed to win, or do you think that this game was always yours to win regardless just because of who you are and how you played?

You know what? I think a little bit of both. It reassured me in the moments where I should've been nervous and I wasn't. But I think opportunity always needs chance, and it was just my chance. It was my turn. I speak so vulnerably about the things that I've lost, and I knew that if I got an opportunity like this, that I would walk away from it as the winner, because I've lost so much, so I think it was honestly destined that I was able to come in and show people how to play a authentic and real game.

I've gotten so many messages and DMs from people across the world saying that they are so glad that they see somebody talking about loss, because they've lost their parents. People that are depressed are now coming and saying that I made them laugh and they haven't laughed in three months. I think I needed this, but I think the people that were able to take all of this in and go on the ride with me, I think they needed it as well. But I think it was destined. Everything happens right when it's supposed to.

That's amazing. Watching you win also really capped off this season as maybe the most feel-good season yet.

Yes! You're giving me all the feels. I'm tired of crying today.

As you were continuously ranked so high, did you ever get worried that other players were going to start to target you because of that?

I honestly think that I didn't realize I was a threat until the, "Are you scheming your way to 150k?" I was like, "They're going to start coming for me." The target on my back got really, really big. And after Crissa went home, that really impacted my game, because she was going to be my No. 1 alliance, and I was planning to align with her and Yu Ling. When that fell through, I literally prayed and journaled every night. The night Crissa went home, I got on my knees, I said a prayer, because I know how the game works. I was like, "God, if somebody doesn't come in here and if they don't fall in love with me, I'm not going to bring this home. I really need some help." I remember crying myself to sleep that night, because I was like, "I've got to re-strategize. I don't have a close relationship with anybody right now like I did with Crissa."

The next day, I woke up and Trevor/Imani was coming through, and I was like, "Okay." Then when they picked me for the antivirus, I was like, "Wow. God already has answered my prayer that I just prayed last night, because they came in, they recognized me, they saw me for my true self, and they gave me the antivirus first." So I definitely felt a bit of a way after Crissa left, but once that happened and I got the antivirus, we rolled right on to the end.

After everyone's identity was revealed at the finale, which catfish surprised you the most?

Oh my god, f---ing Imani! If you would've told me to bet your bottom two teeth that Imani was real, I would've bet my bottom two teeth, and I would be toothless right now. The fact that she walked through, and it was not only not her, but it was Trevor, and as a Circle fanatic, knowing DeLeesa and following the journey, I'm like, "What?" I was shocked. My heart was in my big toe.

Were there any alliances or conversations that were really important to you that happened in the game but we didn't actually see in the episodes?

There was a little exchange with me and Mr. Eversen. It was kind of like a little cringey flirt scene. I don't know if he was flirting with me because he was flirting, or he was flirting just to be flirting with everybody, or if he even thought it was flirting. He may have thought he was just being funny, but there was a very hilarious conversation that happened between me and Eversen that did not make the cut. It was absolutely hilarious.

Wow, I'm so bummed that they didn't show that!

Listen, me too, because I was like, "I'm either going to cringe, or it's going to be so funny."

What was it like watching this season, seeing how the people on the other ends of your conversations were acting while you were messaging with them? Did anyone surprise you?

I was the most surprised when Bru thought that I was coming for him. I made a comment about, "Bru, you're not the only one that looks good in a turtleneck." I think he thought I was coming for him, but I wasn't coming for him. I just remembered that Bru had a photo of him in a turtleneck, and I was trying to just, you know ... I call myself a wordsmith, trying to be cool with my words and make cute little fun things funny, and it went the whole wrong way.

I think that was probably the biggest thing, hearing a lot of people say that they didn't know where my loyalty lays, or where they stood with me. That was just interesting to hear, because I kind of see where they were coming from because if I didn't have a connection with you, a genuine connection, or I felt that you didn't know me, I never showed my hand to anybody until I felt that. I never wanted to have a conversation with anybody just for it to be strategic. If I'm having a conversation, I want to be having a connection. I want to make you laugh. We're being vulnerable. We're doing something. I don't want to talk about, "How do you feel about this," or gameplay. I want to get to know these people, and I want to be fully engulfed in this experience of a lifetime.

That clearly worked out for you in the end. What was it like for you actually living in that apartment and playing in The Circle that doesn't really come across in the episodes?

Oh my god. I think what doesn't come across in the episodes is that we are very busy. On the show it looks like it's just so fun, but there were times where I was like, "Okay, I need a break. I need a nap. I am tired." We were really working. There's just so much that goes into these scenes and these things that you don't really see.

The Circle season 4 is now streaming in full on Netflix.

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