Before the conversation properly begins, the episode front-loads its most jaw-dropping moments in a punchy cold open: Colton's admission that he kept a folder of women's photos on his phone, that he prayed to God to make him straight, and that The Bachelor was an attempt to trap himself into heterosexuality. Paul's warm but direct opening sets the tone — this is a conversation that will go places most celebrity interviews won't. Viewers are invited to follow and tap the bell before the real story starts.

Paul opens with a childhood photo of a gap-toothed Colton on a homecoming float with his Junior Football League team in small-town Illinois. Far from the genetic sporting destiny implied by two All-American parents, Colton was a hefty, awkward kid who never felt talented enough and tried to quit every week. His father coached the team and pushed him hard — but without favouritism, which made the frustration worse. It wasn't until sophomore year of high school, when Colton grew three or four inches and his body finally caught up with his family's expectations, that everything clicked on the field. The same puberty that unlocked his athletic potential also delivered the realisation he was gay.

Paul asks whether Colton had any gay role models in his teenage years. The answer is starkly simple: there was exactly one out gay kid in the entire town, and he was the punchline. Coaches and players openly used his name as a shorthand for weakness or failure, with zero self-awareness. Colton describes this as being 'dough still being formed' — absorbing the messaging that gay meant shameful at the exact age when he was realising he was gay. There was barely any racial diversity either; a handful of Black students in the entire town. College would be the first time Colton encountered anything resembling a diverse world.

Contrary to what many children of divorce experience, Colton never blamed himself — he blamed his parents for hypocrisy. Having been raised Catholic in a family that never discussed divorce, and having been forbidden from quitting anything, he was furious that they were 'quitting' their marriage. But that anger gave way to something more nuanced: the divorce humanised his parents, knocking them off the pedestal of elite athlete perfection he'd placed them on. Today he describes individual friendships with both his remarried father and his oversharing mother, and credits the experience with teaching him to have direct, honest conversations in his own relationships rather than letting resentment fester.

This is the longest and most revealing chapter of the episode. Colton explains his increasingly elaborate system of self-concealment: telling college friends he had a girlfriend back home, and home friends he was seeing someone at college, so the two groups could never cross-reference. He joined FCA (Fellowship of Christian Athletes), attended Bible study, and prayed sincerely to God to make him straight ^{[1] — Colton Underwood "Colton prayed to God to make him straight, joined The Bachelor believing the public heterosexuality would trap him into straightness, and e…" 18:24 Play} . To survive the locker room, he kept a folder of women's photos on his phone ready to produce at a moment's notice. For the rare same-sex encounters he did allow himself, he imposed an iron rule: married men only, because they had more to lose. The emotional cost was profound — he became expert at severing his own feelings, a learned skill that still affects his marriage to Jordan today. Paul gently names the experience as chronic internalised homophobia, and Colton agrees that watching Ellen on his small dorm TV was sometimes his only therapy.

Colton's college trajectory was impressive: All-American on every list, record-breaking junior season. But a senior-year injury and the loss of his standout defensive partner torpedoed his draft stock. Going undrafted stung, but Colton chose the Chargers' $3,500 offer over the 49ers' $15,000 on the strength of his agent's advice about roster chances ^{[1] — Colton Underwood "$3,500 signing bonus: Colton's NFL signing bonus with the Chargers was just $3,500, illustrating the financial reality for undrafted free a…" 27:14 Play} . Life on the practice squad — mimicking opposing stars like Gronkowski to prepare teammates for games — paid $3,800 a week on a rolling contract with no security. He made six figures in his first year playing a sport designed for children, and he found a way to hold onto that perspective even when the business side of the NFL began to disillusion him.

The NFL locker room was paradoxically less homophobic than college — grown men with families didn't gossip the same way — but the league's institutional hostility was obvious. Michael Sam, the SEC Defensive Player of the Year and Colton's 2014 draft classmate, came out before the draft, fell to the 7th round, and was cut ^{[1] — Colton Underwood "SEC Defensive Player of the Year Michael Sam fell to the 7th round after coming out, got cut, and was briefly picked up by the Cowboys — Co…" 31:20 Play} . Colton watched a locker room publicly applaud diversity while privately mocking Sam, and he describes the Cowboys signing as a cynical jersey-sales exercise. For Colton, calculating the risks as a defensive end — weighing what he stood to lose — led him to the same conclusion every time: stay silent. Even now, he admits strength in numbers might have changed things, but as a borderline practice-squad player, he had none of Sam's leverage.

Paul breaks from the interview to endorse Saily, an eSIM app used by his team on the LA trip. The pitch covers the app's core value: avoiding expensive international roaming charges in over 200 destinations. Additional features highlighted include built-in web protection, ad blockers, and the ability to set a UK-based online location to access geo-blocked content from abroad. Viewers are directed to the App Store and offered 15% off their first purchase with code WNTT.

With his NFL career over after a shoulder injury and year-long arbitration, Colton told his father he wanted a year off football for the first time in 17 years. He deployed his settlement money as runway and 'fell into' the Bachelor franchise — first Bachelorette, then Bachelor in Paradise, then The Bachelor itself, filming all three back to back without time to adjust. The show's producer psychology is described with grudging admiration: they're 'basically very good therapists' who had Colton disclosing his virginity on night one of Bachelorette before he knew what was happening. The fame snuck up on him: the moment he popped his head onto a Kane Brown concert stage and the crowd went wild was the first time he realised his life had fundamentally changed.

Colton had planned to reveal nothing about his virginity, but within minutes of sitting down with Bachelor producers — who he now recognises as skilled psychological interviewers — he had given them everything. The virginity narrative became his entire Bachelor storyline, which he resented for multiple reasons: it invited digging, it conflicted with his actual secret history of same-sex encounters, and it put him in the uncomfortable position of wondering whether he was a virgin 'for the right reasons.' He also confesses that part of him believed having sex with a woman might finally make him straight — each milestone (engagement, marriage, sex) was another rung on his self-imposed conversion therapy ladder.

Even while filming The Bachelor, Colton was still managing the mechanics of concealment. His most surprising revelation: he got a large cross tattooed on his entire wrist specifically to be identifiable — the idea being that anyone who claimed to have hooked up with a cross-tattooed man could be traced back to him. When that logic felt risky, he simply wrapped it in a bandage and claimed a wrist injury ^{[1] — Colton Underwood "Got a cross tattoo to create gay cover: Colton tattooed a large cross on his wrist as a deliberate identifier, then covered it with a banda…" 48:57 Play} . The interview underscores how exhausting and self-defeating this management of identity had become: every new layer of 'protection' added new risk and required new lies, yet he couldn't stop. Paul's observation that the fence jump might have been an escape from the facade, not just the show, lands visibly with Colton.

When Colton discovered producers had manipulated his top-3 relationships — the only thing he'd asked them not to do — he headed for the fence. He explains the physics dispassionately: adrenaline is powerful, the gate was locked, he cleared a 6-footer in boots and jeans ^{[1] — Colton Underwood "Jumped 6-foot fence in Portugal on The Bachelor: Colton famously jumped a 6-foot fence in Portugal after discovering producers had manipula…" 50:10 Play} . The escape plan was methodical: find the US Embassy, get an emergency passport, book his own flights home from Portugal. Instead he got lost for two hours wandering alone in the dark. Paul's question — 'Were you trying to escape the show, or the facade you'd built over the years?' — produces the most reflective answer of the episode. Colton agrees it was both: a culmination of 'what the hell am I doing?' that extended far beyond reality television.

Colton loved filming The Traitors — he calls it his favourite project ever, partly because the show's campy, Alan Cumming-hosted theatrics are 'so gay at its core.' But the backlash was severe: fans mapped his ruthless game-playing onto a dark period of his past, creating what he describes as a slow-motion train wreck of dogpiling and false narratives that escalated to death threats against him and Jordan ^{[1] — Colton Underwood "Colton loved filming The Traitors — but fans linked his aggressive game-play to a dark incident six years prior and the backlash escalated …" 56:17 Play} . The production had to intervene publicly. Colton's response is measured: he has apologised repeatedly for his past, he acknowledges the audience wasn't present for his years of therapy and transformation, and he is not prepared to keep re-litigating it. He draws a sharp distinction between who he is as a television character and who he is as a husband and father.

In a warm branded segment, Paul is playfully called out by his sister Kate for being a texter rather than a caller, despite his career as a communicator. The iD Mobile partnership with Mental Health UK carries a simple message: a phone call conveys humour, emotion, and presence that a text message cannot. Paul commits — on air — to calling more. The segment ends with the show's tagline: 'We are truly here to connect.'

This short, dense chapter covers the darkest stretch of Colton's life. After The Bachelor wrapped and the relationship ended, with no identity left to hide behind, he was in West Hollywood taking Xanax at every meal alongside an antidepressant and alcohol ^{[1] — Colton Underwood "I was like playing myself through a video game. I just sort of had this overhead view of myself living my life. I had no consequences. It's…" 1:07:08 Play} . He describes the resulting dissociation — an overhead view of himself living his life with no sense of consequences — with the clarity of someone who has done real therapeutic work on it. The worst stretch lasted about two weeks. He is honest that his doctor wasn't getting the full picture of his mood swings, and that the combination of substances was making it easier to look away from the blackmail situation that was simultaneously unfolding.

The blackmail arrived as an email to Colton's publicist containing precise factual detail — dates, times, locations — of a same-sex encounter Colton believed had been photographed without his knowledge ^{[1] — Colton Underwood "A blackmail email containing precise date-and-time details of a same-sex encounter landed in Colton's inbox while he was taking Xanax three…" 1:07:49 Play} . He denied it at first, then let his team handle it. His publicist — himself a gay man — eventually called Colton in his grandmother's driveway in Illinois and asked one direct question: 'Are you gay?' Colton answered yes immediately, for the first time in his life. That single moment cracked everything open. The Netflix documentary came together with the same executive producers who had been present from the start. Colton's family came next: his mother over dinner the night before the cameras rolled, his brother second, and his father on camera — whose off-camera verdict was: 'Go be gay. Just don't become a Democrat.'

In the second of Paul's planned surprises, he shows Colton a photo from The Bachelor featuring Colton and his father. Colton reflects on the reverence he has always had for his dad — the football coach, the mentor, the problem-solver — and how coming out to him demanded the most trust. The father's immediate instinct was to take the burden: 'Who can I tell for you? How can I take this off your plate?' That response, Colton says, was entirely in keeping with who his dad has always been.

Gus Kenworthy organised a rooftop party in downtown LA for 30 gay men to welcome Colton into the community after his coming-out documentary wrapped. Jordan was there; they barely spoke. Two months later, fate stuck them in Provincetown together for a rainy Memorial Day weekend with no escape from each other's company. They fell in love over one weekend. On one of their first proper dates, Jordan mentioned wanting kids. Colton said so did he. That level of intentionality and alignment on a first date felt unmissable, and it was. Five years later — married for two — they are co-parenting son Bishop together.

Colton unpacks the legal landscape of same-sex family building in the US with striking specificity. He cites Family Equality's finding that 13 states still permit open discrimination against same-sex couples in adoption ^{[1] — Colton Underwood "In 13 US states it's still legal to refuse same-sex couples in adoption. Colton and Jordan navigated two-plus years of surrogacy, birth cer…" 1:21:43 Play} . He describes birth certificates listing a surrogate or egg donor as a parent, nurses refusing to admit both fathers, and the enormous financial burden — most insurance still does not cover IVF. In California, he and Jordan were able to list 'Parent 1' and 'Parent 2,' a detail that felt small but mattered enormously on the day Bishop was born. His central argument: the deliberateness and cost of the surrogacy process is itself a testament to the quality of the parents who undertake it.

Paul's final surprise is a letter from Jordan, read aloud by Colton. Jordan describes Colton as the embodiment of a husband and father: hard-working, playful, never looking back once a decision is made, and with no grass-is-greener instinct. Watching Colton become a father, Jordan writes, helped him relax into their life together. He signs off: 'In short, he's the best person I know, and Bishop and I are so lucky he's ours.' Colton's response — 'he's way better with words than I am — I want to frame this' — is one of the episode's most human moments.

Colton explains the genesis of Dear Bishop: a practice he and Jordan share of writing emails to their son's email address after every notable moment — first roll-over, first headbutt, first 'dude.' That collection of dispatches crystallised into a short audio book narrated entirely in Colton's voice ^{[1] — Colton Underwood "Colton and Jordan write emails to their son Bishop every time he hits a milestone. That collection became the audio book Dear Bishop — narr…" 1:28:05 Play} . He's transparent about its dual purpose: part time capsule for Bishop, part accountability document from himself. His first book contained 'safety lies' — omissions that protected him when he wasn't ready to be fully honest. Dear Bishop corrects the record, addressed directly to a child not yet old enough to hear some of it. Paul calls it inspiring for all parents and suggests dads especially should consider recording audio voice notes of their children's milestones.

Paul asks the question every reality TV alumnus gets. Colton's answer reflects his evolved relationship with fame: he stopped saying never after years of unexpected career turns. The right project depends on what his soul needs at any given moment, and that changes. He would happily do another Traitors season, describes himself as still technically 'on his year off' from football, and notes that 15 minutes of fame has somehow lasted almost a decade. The lightness is earned — the conversation has travelled a long way from the person who prayed to be straight.

Paul's standard closing question asks every guest for their most defining conversation. Colton's answer goes straight to Jordan saying 'I love you' for the first time ^{[1] — Colton Underwood "What I would say is that is 15 versions of me ago. Meeting Jordan, getting married, having a kid, all of those things change you in like th…" 1:00:25 Play} . He'd been waiting for Jordan to go first, not knowing exactly why — just a gut connection. When Jordan said it, Colton felt everything drop: the guard, the conditions, the performance. The lesson he takes from it is that he could finally be who he was born to be. Paul closes by reflecting on how profoundly Colton's parents' imagined version of his future partner — defined by their conservative, sporting, Midwestern expectations — is absent from Jordan, and how that turns out to be the truest possible outcome.

Paul delivers his personal debrief: the image of Colton hiding therapy sessions in his father's closet and car while the whole world saw him as a Bachelor celebrity is almost surreal. He notes Colton's ownership of his control-freak tendencies and draws on his own experience playing defensive end to understand why risk calculation became Colton's dominant life skill. The episode closes with a clip of Josh Cavallo, the Australian footballer who became the world's first openly gay top-flight player, describing the violence and isolation he faced coming out — and the love that followed when his team rallied behind him. The juxtaposition of Colton's American story with Cavallo's Australian one underscores that the fight for inclusion in elite sport is far from over.