The Great Escape: On the Moment That Came to Shape The Bachelor Forever


It’s a dark November night, and Colton Underwood has finally escaped The Bachelor. He runs wildly in the direction of any light he can find, with the intention of acquiring a new passport (producers had his current one) and fleeing the country. Moments before, he’d been dumped by the girl of his dreams; producers had flown her father out to Portugal, where the show was filming, to convince her to send herself home. Underwood had then taken his wallet, torn off his microphone, hit a camera, jumped over a seven-foot-tall fence, and fled into the Portuguese wilderness. He’s a six-foot-four athlete—a paragon of physical strength. He makes the feat look easy. Cameramen chase after him, their footage shaky and dim, and producers call out for the host of the show, Chris Harrison. Harrison appears out of nowhere like always—does this man ever sleep?—and calls out for Underwood, yelling, “He just jumped the fucking fence!” By the time the crew opens it, Underwood is gone. Bachelor Nation would never be the same.

When Underwood first jumped the fence in 2018, nobody knew except those who witnessed it firsthand—producers, Harrison, and Underwood himself. But when the first preview of The Bachelor’s 23rd season aired, the fence jump was front and center. Nobody knew why or when it happened, but it was clearly the climax of the season. It became highly anticipated; recap blogs often featured lines such as “Nope, Colton still hasn’t jumped that fence,” “All we want to do is to see the Bachelor jump over the fence!,” and every week in which Colton [doesn’t] jump over a fence [feels] like a betrayal of trust. And on the day that the fence jump finally aired, fans went into a frenzy. For the first time ever, a Bachelor had quit the show, effectively exposing it as the artificial human experiment it was. Sure, everybody knew that The Bachelor wasn’t real; it wasn’t like production tried to hide the cameras. Some people thought the show was completely scripted. But to see microphones thrown to the ground, producers who didn’t know their next move, and the staff on the show desperately trying to salvage it by searching for their missing lead (who eventually turned himself in on camera) was different. It openly displayed the show’s façade, because the façade had finally fallen apart—and, more importantly, it explicitly demonstrated what happens when people get fed up with being trapped in the manufactured bubble of reality TV.

After the episode aired, people made fence cakes and sold fence merchandise. Bachelor recap videos recreated the iconic moment when it all went down. The Washington Post did a simulation of the fence jump to try to measure how Underwood managed to pull off such a maneuver. Recap articles celebrated the moment living up to expectations, and all contained the same word: finally! Underwood appeared on This American Life to explain how long he was on the run for (two hours), and how he’d managed to avoid production (hiding in ditches and behind cars). He also discussed how the show had negatively impacted his life, and encouraged other contestants to do the same. “People don’t understand that this is my real life,” he said. “This scarred me and jaded me.”

I feel like I’m exposing myself. I’m not embarrassed to be a fan of The Bachelor—in fact, I’ll openly offer this information to anyone and everyone who brings up the franchise. But the extent to which I watch the show is, admittedly, a bit extreme. I haven’t missed an episode since 2016. I listen to two hour-long podcasts each week, and belong to several Bachelor Facebook groups. When Underwood’s season aired, though, I finally felt a little bit dignified about my obsession. Viewers were beginning to scrutinize The Bachelor in a way that they hadn’t before, and even non-fans were realizing that it was a piece of media worthy of serious analysis.

At the end of the season, Underwood finally got the girl, a 24-year-old from Orange County named Cassie Randolph. But the two did not get engaged (as is customary), and Underwood broke up with the remaining contestants a week early, effectively throwing the format of the show out the window. The finale ends with another acknowledgement of the show’s artifice, and what it had done to its two leads. Underwood and Randolph take their mics off of one another and escape from the cameras forever, finally free to live their own lives.

Fast forward to 2022. Eight seasons and one tell-all book later, Underwood is openly gay and Randolph has filed a restraining order against him. Chris Harrison is no longer the host of The Bachelor; he stepped down last spring after making controversial statements about a racism scandal on the show. It’s now commonplace for the show to not end in an engagement. In many ways, the façade of The Bachelor has been exposed and is now an active element of it. Contestants explicitly discuss producer manipulation onscreen, and some of the most popular Bachelor Nation podcasts and blogs view the show from an analytical standpoint, bringing the “real world”—editing and production, strategy, social media, and even politics—into their discussions of it. Game of Roses, for example, is a popular podcast that frames The Bachelor as a professional sport, as well as a reflection of American culture and society. Each week, its hosts Chad Kultgen and Lizzy Pace release a news segment called “Bachelor: State of the World” in which they directly relate The Bachelor to current events. Kultgen argues that “in an era where we’re just coming out of a four-year presidency with a reality-television show host as president, I don’t think anyone can ever say reality TV is frivolous and meaningless anymore.”

Justine Kay and Natasha Scott, hosts of the podcast 2 Black Girls, 1 Rose, also focus on critical analysis in their discussions of the Bachelor franchise. “The franchise has established such a reach that it is essentially an American pastime and staple in American culture for millions of Americans,” they told Vanity Fair. “With that level of power and influence, they absolutely should be scrutinized, held to a high standard, and held accountable.” Kay and Scott are part of a growing group of Bachelor analysts who understand that as the world changes, reality TV must change with it. The hosts of Game of Roses have pushed reality TV contestants to unionize, and end each episode with a reminder that viewers of The Bachelor are complicit in the wrongdoing within the franchise, and in the destructive impact it often has on contestants’ lives.

Looking back on Underwood’s season, it seems like a relic of the past, a time in Bachelor Nation long-gone when we watched just for fun, without taking it so seriously; when the show existed in a vacuum, and provided an escape from the real world, not a reflection of it; when it was uncomplicated. More and more, though, viewers are beginning to understand that this is far from the truth. The Bachelor has always been reflective of American culture, and the world outside the bubble, in a major sense. We just didn’t realize it.

The Beginning

In March 2002, 16 years before Underwood jumped the fence, The Bachelor premiered on ABC. Although it has evolved over the years in style and format, its central principle remains consistent: people want to believe in love. 

Los Angeles Times writer Amy Kaufman’s book Bachelor Nation provides a little more insight. Kaufman explores the question of why The Bachelor has remained so popular for so long, and concludes that we watch it as a way of coping with our own anxieties about dating in a much more mundane environment. The Bachelor, she writes, “allows us to see a world filled with courtship, chivalry, and romance—and while we may scoff at the helicopters and hot tubs, deep down I think many of us still long for those kinds of things…Love, of course, is something we’ve all experienced—but not in the way The Bachelor depicts it…It gives us hope that a frothy, beautiful love story is just out of reach.”

Scott Jeffress, the show’s co-executive producer for its first seven seasons, would agree. He claims that when The Bachelor first aired soon after 9/11, people didn’t want to consume depressing media. Instead, “They wanted to have a fantasy. They wanted to imagine what could be and be happy. I truly think that’s why The Bachelor hit at the perfect time.”

Lisa Levenson, the producer who frequently receives credit for creating the exaggerated soap-opera aesthetic of the show, also states that her main goal was to make viewers get lost in the fantasy: “We took it to a level that was way out there. We would have thousands of candles ready to go.” 

But fans of the show know well that the love story doesn’t always work. Out of 44 combined seasons of The Bachelor and The Bachelorette, only nine couples remain together—and with the rise of social media presence as a key element of the franchise, the reality of post-Bachelor breakups has become more and more visible. And what’s the point of becoming invested in a love story that you know will most likely end? By 2018, Bachelor Nation was becoming disillusioned with the fantasy.

In Bachelor Nation, Kaufman also includes interviews with celebrities who explain why they watch The Bachelor. Often, their responses are not about love at all. “It’s really just a behavioral study,” Amy Schumer says. “What will these people do? They cast these women who are very confused and unstable. I like awkward moments…and it’s the thing I most look forward to every week.” Allison Williams says, “I think that this is a show where you can learn about and engage with your own sense of feminism…I find myself wishing the characters would just say, ‘Let’s…start dating and see if we actually like each other in the real world.’…And increasingly, it feels absurd that they don’t know anything about what’s happening in the outside world…I would give anything to see a political discussion.” 

So, maybe I should amend my above statement: whether it’s love, politics, secondhand embarrassment, or a general fascination with how humans react to the laboratory environment of reality television—and whether it’s conscious or not—when people watch The Bachelor, they look for something that they can believe in, period. After over 30 seasons, however, the show itself was failing to deliver the entertainment factor that many had come to expect from it. Starting in 2015, its viewership began to trend consistently downward.

In September 2018, three months before Underwood jumped the fence, ABC announced that he would be the next Bachelor. Underwood was a tall, beefy former football player who’d come in fourth place on the previous season of The Bachelorette earlier that year. Immediately after, he appeared on The Bachelor in Paradise, a spin-off in which Bachelor Nation fan-favorites all spend about a month on a beach in Mexico dating each other in various combinations. Underwood seemed like a traditional choice, a cookie-cutter-attractive, all-American man—the kind of person who’d immediately come to mind when you think of “the Bachelor.” Bachelor fans typically characterized him as a big Golden Retriever type.

Following the official announcement, fans assumed that the season would be boring and conventional, just like Underwood was. Vanity Fair wrote that The Bachelor was “staying the course despite flagging ratings for multiple disappointing seasons” through choosing a Bachelor who’d cooperate with producers to create a by-the-book season. Fans on Twitter called Underwood a “yawn…in physical form” and an “indecisive vanilla manchild.” The Washington Post released two articles on the “uniformly negative” reactions of fans, and characterized Underwood as the “blandest guy alive.”

On Underwood’s first night as the Bachelor, 55 days before the fence jump, he participates in all the regular night-one rituals: a pre-show interview with Chris Harrison, filming B-roll where he pensively walks the grounds of the mansion where the first two weeks of filming take place, and greeting his 30 new girlfriends as they each try their best to impress him. 

Underwood meets Bri, who pretends to be Australian; Heather, whose occupation is listed as “Never Been Kissed”; two Miss USA contestants; and 10 women below the age of 24, a record high for the show—all of whom claim to be ready to get engaged. Cassie Randolph appears in a long floral dress with a box of fake butterflies and spills a few on the ground. “You give me butterflies,” she tells Underwood. After she leaves, he picks up a butterfly and puts it in his jacket pocket. Ultimately, he gives his first impression rose to Hannah Godwin, an Instagram influencer and former beauty pageant contestant from Alabama. Afterwards, producers ask Underwood who he’s interested in and wants to take on a date, and he tells them Hannah. The premiere also cuts away to Bachelor watch parties across the country, as if the show is trying to convince its audience that people are still excited about it. 

Entertainment news sites deem this the start to another conventional, uninteresting season: Entertainment Weekly calls it “pointless,” and ABC’s own blog calls it “ugh.” Vulture’s recap skims over the episode and ends not with analysis or predictions for the season, but instead a standalone sentence: “Then, in the ‘Coming up this season’ tease, Colton leaps over an eight-foot fence in one smooth motion.”

What We Didn’t See

Already, there was more to the season than what may have met the eye back in 2019. This is true for every season of The Bachelor. We suspect it. We talk about it. But Underwood was one of the first contestants to actually acknowledge it. In August 2019 and September 2020, he recorded two interviews with people previously almost foreign to the Bachelor franchise. First, Underwood appeared on NPR’s This American Life, marking the first time that most people had seen a serious news organization cover a show like The Bachelor with sincerity and depth. Next, Underwood recorded an interview with Reality Steve, a popular blog by Texas native Steve Carbone that provides spoilers for entire seasons of The Bachelor before they air. Carbone has long been seen as an enemy of the show, and has also historically been critical of its artifice and produced nature. NPR had never interviewed a Bachelor before; Carbone had interviewed just one. In these interviews, one of which went to number-one on Apple Podcasts, Underwood revealed that he’d been collaborating with producers in order to be the Bachelor—that’s what he came on the show for.

“I was done with football, so this was my next game,” he told Carbone. “I read spoilers and analyzed who was eliminated. I tried to research who might be the Bachelorette.”

Underwood’s research led to a friendship and brief romance with then-contestant Tia Booth, who’d made the previous Bachelor’s final four. 

“I had not planned on telling anyone in the cast or production about Tia,” Underwood said in the same interview. “But once you’re sitting in the hotel room pre-show for as long as I did without a phone”—contestants have to isolate in a hotel before filming—“your mind starts wandering and it plays tricks on you. I started thinking that I would look like a fool if [that season’s Bachelorette] Becca [Kufrin] called me out right away. So I told one producer in what I thought was confidence. But obviously, once you tell one, everyone finds out.”

Quickly, however, Underwood’s trust in producers dwindled. On his season of The Bachelorette, Booth made two appearances and revealed her past with Underwood; her second appearance resulted in his elimination. Next, he appeared on Bachelor in Paradise, where Becca Kufrin arrived to get “closure” from him and discuss his future relationships. Upon seeing Kufrin, Underwood had a breakdown on camera. He later told Carbone: “When Becca showed up, it felt like it was forced. First they brought Tia out to Becca’s season twice, now I’m in Paradise and I have to see Becca again. So I’m like, can I catch a break? Why do you have to bring these people back in? They’re really just getting me and I think they enjoyed it because I was trying to be mentally tough and I was breaking down. I was overwhelmed because I wasn’t sleeping. You don’t sleep a lot. There was no air conditioning and crabs came in all the time. And I was hungry at all times. And it felt like the cast was against me and people kept showing up who I didn’t want to show up.” 

Underwood attempted to quit the show four times off-camera, and when producers offered him the role of the Bachelor, he reveals that he doubted whether he could go on the show again. “I went through the ringer,” he says. “I mean, I was crying on national TV. My family had never seen me like this. My dad had seen me cry maybe once outside of the show. I went back-to-back, show-to-show-to-show, and I never had a break. I didn’t grasp the magnitude of everything until after my Bachelor season finished.” What Underwood doesn’t know is that he’s the perfect pick for Bachelor. He’s pliable. He listens to producers. He falls for their mind games. He cries when they want him to cry and he self-sabotages at their behest.

During his season, Underwood’s seed of distrust grew when producers didn’t place his first choice, Hannah Godwin, on a date. He started not telling them the full truth; if he wanted to spend time with certain people, he couldn’t let producers get in the way. Quickly, his first choice became Randolph, but he continued saying it was Godwin. At this point, Underwood felt that he had to lie to producers in order to actually try to succeed in falling in love. But this was all before he tore the whole thing to shreds.

Escaping the Simulation

There are several unspoken laws of The Bachelor, ones that are never explicitly said but are heavily enforced. In the final week of filming his season, Underwood will break three:

1: Do not tell the winner that they’re your final choice until the very end, when they’re the only remaining contestant.

2: Only say “I love you” to your final pick.

3: You’re under contract to film a complete season. If your first choice self-eliminates, settle for someone else.

One week before Underwood jumps the fence, he flies to each of the remaining contestants’ hometowns to meet their families. Although there are four left, at this point Underwood is all in on Randolph.

Matt Randolph, father of Cassie Randolph, is serious and practical. He loves his daughters more than anything, and describes Underwood in interviews as “just, you know, a guy.” And before meeting this guy— his daughter’s potential fiancé, a man with four girlfriends whom she’d known for two months—producers took Matt Randolph out to dinner. Nobody knows what exactly occurred at dinner; it happened in complete secrecy, without Underwood or even Cassie Randolph’s knowledge. What we do know is this: producers told Matt that Underwood was going to dump his daughter, and urged him to protect her at all costs. This becomes the entire story of Randolph’s hometown. Matt tells Underwood that he doesn’t trust him, and refuses to give him his blessing to propose.

Three days before the fence jump, Underwood and his three finalists fly to Portugal. On his date with Randolph 12 hours before, they wander the streets of Tavira. They explore markets and dance in squares, and end the day with a picnic overlooking the city. Interspersed in interviews, Underwood says, “There’s just something about her. You can’t describe love…Cassie makes me feel complete…After today, I just know for sure I love [her].” It seems too good to be true, just like The Bachelor is meant to be. This is where Underwood finally breaks the news to Randolph that he didn’t get her father’s blessing. Onscreen, the mood suddenly shifts. Randolph is surprised; she doesn’t know what to say. She cares about her family’s opinion, and for the first time isn’t sure if Underwood is right for her after all. Maybe, she says in her aside interview, they just don’t have enough time. As the two leave their date, Underwood asks Randolph, “You okay?” She doesn’t answer the question.

Four hours before the fence jump, after Underwood and Randolph return from their date, a black car pulls up at the resort they’re staying at. The door opens, and Matt Randolph steps out. Focused and determined, he walks through the hotel. Staff members scatter as they see him. He knocks on a door and Cassie Randolph opens it. Her eyes widen. “What? What are you doing here?” she asks—but she’s happy to see him. They hug. “Oh, I was just in the neighborhood,” Matt replies.

In his talking head interview, Matt says, “I came here because I have a concern with the potential engagement that may be around the corner. The commitment of marriage is important. I want to make sure Cassie is seeing with both eyes open.”

A more correct choice of words would be, “The producers flew me out here.” This is a tactic that Bachelor producers often use to throw a screw in things at the end of a season. Exes, family members, and friends arrive in whatever foreign country the show is filming in as a last roadblock for finalists, who sometimes take the bait and quit. It’s an open secret that producers are behind this; regular people can’t just crash the set of a show that’s filming secretly, with no outsiders allowed, on a whim. One of the first fly-in incidents occurred in 2013, when a contestant’s ex-boyfriend appeared on a hometown date to provoke a fight with the Bachelor in what turned out to be a practical joke. But after this low-stakes operation, producers began to orchestrate fly-in situations with a higher potential impact. In 2014, the Bachelorette’s frontrunner self-eliminated after reconciling with an ex. In 2015, a finalist’s ex left a letter and flowers at her door minutes before her final date. And in 2017, just one year before the fence jump, an ex-fiancée had appeared at a finalist’s hotel room in Peru, where she promptly shut down his attempt to propose. When Tia Booth, Underwood’s ex, appeared twice on The Bachelorette? Producers. When ex-Bachelorette Becca Kufrin appeared on Bachelor in Paradise, leading to Underwood’s public breakdown? Producers. This was the fourth time producers had flown someone in to sabotage Underwood specifically.

Randolph and her father sit on the couch. She reveals how confused she is that her father didn’t give Underwood his blessing. He says that at the time, Randolph seemed conflicted. He asks, “Do you love him?” She replies, “I think I do,” and then after a long time: “Yeah. I just wish I had more time. I don’t want it to be over with him, but it scares me to accept a proposal.”

Matt Randolph replies, “There shouldn’t be any hesitation in your mind about spending the rest of your life with someone.”

Cassie is upset; she’s crying. “I really like him and I really care about him.”

“I know, but you need to be honest with him. You’re not doing him any service continuing this.”

They embrace again. Cassie knows what she needs to do. 

Two hours before the fence jump, both Randolph and Underwood sit down for interviews. Randolph reveals that she’s going to be honest with Underwood. She’s going to tell him that she’s not ready to get engaged, and eliminate herself.

Underwood, on the other hand, is on top of the world. “Spending the day with Cassie has been unbelievable,” he says. “I just keep falling more and more in love with her.” He doesn’t care that he hadn’t gotten her father’s blessing; this issue didn’t even cross his mind. Tonight, he tells the cameras, is the night. Randolph is “the one,” and Underwood is going to tell her that he loves her—his first breach of Bachelor law.

30 minutes before the fence jump, Underwood and Randolph arrive at dinner. They sit down facing each other, with no idea of what the other is thinking. Randolph can’t meet Underwood’s eyes. “So, my dad showed up at my hotel room earlier,” she says to the ground. It’s over.

21 of the past 22 seasons of The Bachelor have ended with a proposal. Underwood says he doesn’t care if Randolph doesn’t want to get engaged—another break in the age-old formula. There are two women besides Randolph remaining, but Underwood doesn’t want to be with them. He’ll choose Randolph no matter what. Another break. For Randolph, Underwood will shatter every unspoken rule. But Randolph has made up her mind.

10 minutes before the fence jump, Underwood walks Randolph to a limo, and, shaking uncontrollably, watches her drive away. Then, he goes silent. 

You’ve got to think,” he tells Reality Steve over a year later, “You can’t just take Matt flying to Portugal for Matt flying to Portugal. You think, Tia came on Becca’s season twice, Becca came to Paradise, now Matt’s flying to Portugal. So it’s a bigger picture that I don’t think a lot of people piece together. When I heard that get dropped at dinner, I was looking for a producer but nobody was even showing their face because they know I know.” Underwood knew, in other words, that Bachelor producers would stop at nothing to sabotage his life. 

And in that moment, Underwood decided that enough was enough. It was time to escape.

The Aftermath

In the season finale, producers hunt down Underwood, who’s lost in the streets of a nearby neighborhood. He walks alongside the road, refusing to look at the cameras they point out of their cars, and only agrees to get in so that he can return to the hotel; he doesn’t have his phone and doesn’t know where he’s going. But he makes his feelings clear: “No, I’m not okay. I’m done with this shit…I’m done with the whole thing.”

The next day, the show is back to its regular polished format, but the illusion isn’t quite the same—if anything, Underwood’s red, swollen eyes serve as a constant reminder of the events of the night before. While watching, I wonder how producers convinced Underwood to put a mic on and accept visitors. But regardless of why or how, here’s the fact of the matter: after some on-camera coaxing from Chris Harrison, Underwood decides that he’s not done with The Bachelor after all. He begs Randolph to take him back before her flight back to the US. She says yes—but with the condition that they will only date, and see how their relationship will pan out in the real world. When they appear on “After the Final Rose,” the show’s where-are-they-now special, Underwood and Randolph proclaim that nothing is holding them back anymore, and that they’re taking their relationship at a regular pace. “Things have been completely different,” Randolph says. “It’s better than I could have ever imagined.” The two-night event marked the first upward trend in Bachelor viewership in years. 

The couple exits the simulation having bent its normal rules and destroyed its fundamental premise; they have not succeeded because of The Bachelor, but in spite of it. It’s a narrative that’s explicitly grounded in reality—not the high-up, lofty ideals that the franchise was founded upon. It’s one that reveals that for those who participate in it, reality television isn’t manufactured at all; it’s a real part of their lives, something that impacts them in a permanent way. It’s one that maybe, just maybe, people could believe in.

If you bring up Underwood now, people might mention the fence jump. Probably, though, they’ll mention more recent events—Underwood and Randolph’s very public breakup in early 2020, Randolph’s subsequent restraining order against Underwood in September (she dropped it two months later), and then, in February 2021, Underwood’s coming-out interview. Underwood’s interview received significant backlash for not addressing his questionable history, and Underwood made no public appearances for several months afterwards. Randolph did not comment on the situation. On December 3, Netflix released a special called Coming Out Colton, in which Underwood navigates life as an openly gay man. I watched Coming Out Colton in its entirety, and witnessed Underwood come out to his close friends and family, confront his high school football coach about past homophobia, and learn to reconcile his identity with his Christian background—all on camera. Underwood also meets fellow gay NFL players, and is mentored by gay Olympian Gus Kenworthy. I was skeptical of Coming Out Colton, but ultimately felt proud of Underwood for grappling with his complicated past head-on and making peace with his sexuality. He speaks openly about what The Bachelor always represented to him—the opportunity to live a closeted, heterosexual life.

But while watching, I couldn’t help but think about the fact that this was still produced—still planned in advance by Netflix, still filmed and mic’d and featuring glamorous celebrities. And even worse, it was claiming to be something that it just isn’t—a completely genuine depiction of Underwood’s life. Nobody ever tries to convince you that The Bachelor happens authentically, in the real world outside the simulation. And this, to me, ultimately felt less honest than the obviously fabricated world of reality television, where couples fly helicopters and get engaged on faraway beaches, where life is static and formulaic—until those historic moments when suddenly it’s not. Coming Out Colton didn’t, couldn’t ever, match up to the authenticity of that night in 2018. 

After watching, my mind kept going back to that night—to the feeling of pure, absolute truth. The yelling, the shaky camera, the collective inhaled breath of America. The reverberations of the jump heard around the world. The white fence, tall and looming. And then, finally, finally, Underwood leaping over it in one graceful, unanticipated movement, and disappearing into the darkness where, for at least a little bit, the cameras could never reach him.