'Bachelor' Colton Underwood on the Moment He Quit: "I Threw Out Every Unwritten Rule"

The most famous Bachelor franchise breakup in recent memory came last year when star Arie Luyendyk Jr. blindsided his fiancee, Becca Kufrin, breaking up with her in a heartbreaking, cringe-worthy and almost unedited one-on-one for ABC's cameras. Monday night's episode of Colton Underwood's season of The Bachelor invoked that 2018 TV moment when front-runner Cassie Randolph flipped the reality dating show's script and exited the show in a shocking breakup scene that temporarily halted filming one week before the finale.

During a 20-minute conversation that was so quiet viewers could almost hear the producers crying off-camera, Randolph broke up with Underwood during the highly anticipated week of overnight dates — called Fantasy Suites — in Portugal. With three women still left in the competition, the Bachelor star, who hinted that he planned to lose his virginity to Randolph ahead of their date, broke show rules to beg her to stay. Underwood told Randolph he loved her and planned to pick her in the end. He even said he wouldn't propose if she was hesitant about an engagement, despite the fact that, in the last 10 seasons, only one Bachelor hasn't proposed during the finale.

But it wasn't enough to change Randolph's mind. She ended their relationship and exited the show, and her actions sent the emotional star, 26, into a tailspin. Underwood, a former NFL player, physically rebuffed the cameras, jumped an eight-foot fence (a moment that had been heavily teased all season long), and ran away from production. The episode ended on a cliffhanger as Underwood disappeared into the woods in the middle of the night. "I have no idea where he went. We're out in the middle of nowhere. Holy shit, he is gone," franchise host Chris Harrison said before the episode cut to black.

Now, speaking to The Hollywood Reporter, Underwood fills in the gaps about when he went missing. "I was gone for a while and, in that moment, I quit," Underwood tells THR of going AWOL during filming. "I didn’t want to be the Bachelor anymore."

THR spoke to Underwood at the taping for the Women Tell All reunion episode (which airs on Tuesday). Clips from the rest of the season and Underwood's presence at the Los Angeles reunion show make it clear that the star does indeed return, but the events of Monday's episode set up a non-traditional two-night finale (airing on March 11 and 12) as Underwood must now figure out how he wants to proceed with his two finalists, who are — by default — Tayshia Adams and Hannah Godwin. The only other time The Bachelor franchise devoted two nights to a finale was for the aforementioned Luyendyk Jr. shocker.

"The show goes on, and I have a very important conversation with Chris in which I share with him that it’s not fair to myself and not fair to these women for me to quit and give up. But yeah — it gets good,” Underwood says about what's ahead. "I had to have some conversations to get to that point."

When Randolph left the show, Underwood says his worst fear materialized. "Just because you’re the Bachelor doesn’t mean you’re protected from heartbreak or you’re automatically guaranteed a relationship at the end of this," he explains. Indeed, Underwood has been hinting all along that he did things "differently," implying that his season might not end with the traditional proposal. "It caught me off guard, and I fought for it with everything that I had. I throw out every unwritten rule of The Bachelor that there is — you’ve never seen a Bachelor say, 'Hey, it’s you,' when other women are still there. You see the fight, so it was tough; it was hard.”

Underwood laid all his cards on the table in fighting for Randolph to stay, which is why it seems unlikely that the Bachelor will turn around and end up proposing to either of the remaining two women. Months have passed since that moment in Portugal, however, and now Underwood stands by the decisions viewers will see him making in the end.

“While you guys get to see this TV show, this is my life," he says. "So I’m not going to make a rash decision, and I’m not going to do something that is going to have an impact on the rest of my life unless I’m sure about it."

The Bachelor has a history of bringing back contestants who may have left too soon to tie up storylines, so anything is on the table for the two-night ending, which will broadcast live both nights. That means Harrison will open the show in real time and cut back to pre-taped footage to show how Underwood's show journey ended.

In the months since taping has wrapped, Underwood has said he is the happiest he has ever been, possibly alluding to finding love after all. Another sign that he does appear to have found what he's looking for at some point between Portugal and today is that the swirling question of whether or not he is still a virgin will also be answered next week.

Underwood's virginity has been a steady topic throughout his season, with all three of his finalists sharing their thoughts and conversing on camera about his personal decision. Randolph was hesitant to have that intimate moment between them play out for the cameras, and Adams said she waited until her first marriage to have sex and understood Underwood's values.  

“It’s part of the finale," Underwood tells THR of the question about his sexual experience — one he cannot escape. "It’s part of me now, it’s part of me going forward. I get that everybody has those questions. I spoke very openly and candidly about it when it was me, and when you’re in relationships, it changes the dynamic because you’re also talking about other people now, and you’re not just talking about yourself."

He adds, "I can’t lose my own virginity by myself. That’s not how it works, I think."

The Bachelor: Women Tell All airs Tuesday at 8 p.m. on ABC; The Bachelor finale aires March 11 and 12 at 8 p.m. on ABC. Head here for all of THR's show coverage.

Kirsten Chuba contributed to this story.