The Boom Boom Room is an Are You the One? staple: The private getaway is the ideal location for potential (and newly confirmed) Perfect Matches to get to know each other without others around. And during tonight's Season 8 kickoff, Kai earned a special distinction in the series' run: entering the private space with two different love hopefuls in the same evening (timing is key; repeat cameos with differing partners is not). Oh, and Jenna and Remy are also a part of this special footnote as well.

So how did this history-making feat unfold? First, some background on Kai.

"I am a queer, trans-masculine, non-binary human whom has chosen to medically transition," Kai revealed at the beginning of the installment, while adding that the pronouns of choice were he/him and they/them. "Non-binary means that I don't prescribe to either male or female, I'm somewhere in between. I biologically was female, but when I was born, nobody consulted me and was like, 'Hey, do you like this name? Does this gender feel right for you?' All of a sudden, it clicked for me that the box wasn't locked. I could step outside the box and be like, 'Okay wait -- I'm allowed to choose."

Jenna was quick to notice Kai (mere moments after hellos were exchanged) and quickly gushed (out loud), "He's so hot -- he's totally my type."

The two promptly separated themselves from the rest of the group on night 1, as Jenna confessed that she prides herself on being "emotionally intelligent." Music to Kai's ears, obviously.

"Physically, she's very much my type, and you start talking to me about emotional intelligence, and I'm like, 'Talk to me more,'" Kai admitted. "For the first time in my life' I feel really attractive. That's big for me."

There were exchanges of "you're dope" face-to-face and Jenna stating solo that this experience with a trans person didn't feel "any different." And that's when this happened:

From there, the two continued to bond: Jenna watched Kai administer testosterone shots ("You are inspiring as f*ck, and I appreciate you," Jenna told Kai during the moment), and it seemed that the connection was only intensifying. There was a jealousy mishap (Jenna got upset when Kai was spending time with some other people), but the pair thought it would be best to make out up in the BBR. As the other love hopefuls listened outside.

But when they exited -- and Jenna stated it was time for bed -- Kai began talking to Remy.

"I'm really good at dating, but I'm not good at relationships," Remy declared. "I can date like 8,000 people at a time, but it's really hard for me to be in a relationship with one person."

"I'm getting attracted to you -- stop," Kai disclosed. "I think you're really f*cking hot."

Remy, meanwhile, wasn't phased by Kai's connection to Jenna -- and made a proposition Kai couldn't refuse.

"Do you just want to go to the Boom-Boom Room and, like, f*ck?" Remy posed.

And away they went. Jasmine's narrative on the situation?

"Kai, you just left the Boom Boom Room with Jenna, and now you're going with Remy. Twice within two hours," Jasmine stated. "I feel you, if that's what you want to do. But don't get yourself too caught up in that Boom Boom Room feeling."

The next morning, Kai told Jenna what had unfolded -- and Jenna admitted jealousy and annoyance. Jenna vowed to be "logical" with these emotions, while Kai admitted Jenna's "reasonable" reaction was confusing.

"I'm not really sure if that's a good or a bad thing," Kai added.

Good or bad, Kai is now in a special AYTO league. What will this mean moving forward? Will it dampen or strengthen Kai's bond with Jenna? Tell us your thoughts, then don't miss Kai (and the rest of the cast) every Wednesday at 9/8c.