My Journey with the Walter Boys: Ashby Gentry on Navigating Love Triangle Challenges

Season 2 of My Life With the Walter Boys has finally arrived, and Ashby Gentry steps back into the complex role of the love triangle’s other guy. His character, Alex, features plenty of swoonworthy moments, but being the less favored romantic interest comes with its unique challenges — including heartbreak and backlash.

“I believe my body and mind are getting ready for people to start discussing me again,” Gentry, 26, told Us Weekly exclusively before the season 2 premiere on Thursday, August 28. “I don’t shy away from it because that seems pointless. I stay active on social media; limiting my life because of people’s comments isn’t something I want to do.”

He added, “Some actors take that route, and if it suits them, that’s great. While it doesn’t always affect me, it can hit hard sometimes. It would be unrealistic to claim that it doesn’t hurt me when people say certain things.”

Warning: Spoilers ahead for season 2 of My Life With the Walter Boys.

Since its premiere in 2023, Gentry has portrayed Alex Walter, a stable and thoughtful character, opposite Noah LaLonde’s brooding bad boy, Cole. Together, they form the emotional core of the show’s love triangle involving Nikki Rodriguez’s Jackie, who moves in with the family after suffering a tragic loss in a car accident. In Colorado, she finds herself torn between the dependable Alex and the thrilling Cole, a familiar dynamic in the teen drama genre that invites passionate scrutiny from a dedicated fanbase.

The challenge intensifies for actors portraying the less favored romantic interest. While Alex dates Jackie in both season 1 and season 2, she ultimately chooses Cole — not once, but twice. Their chemistry has gained immense fan support, leaving Alex in a vulnerable position.

“Our fanbase is predominantly young. They haven’t quite matured,” Gentry remarked. “Still, when the [season 2] trailer dropped, I felt genuinely disheartened. I thought, ‘Here we go again.’ … It was a bit like when Conrad says in The Summer I Turned Pretty, ‘My chest hurts, physically hurts.’ I felt that way seeing our trailer, like a weight on my chest.”

Interestingly, Gentry shared his empathy for star Gavin Casalegno, who portrays Jeremiah, the less popular side of another love triangle with Chris Briney’s more favored Conrad.

“Since we’re often compared to The Summer I Turned Pretty, discussing that connection seems fitting. I told some people recently, ‘I really feel for Gavin [Casalegno],’” Gentry admitted. “I don’t know him, but I think some of the hate I’ve received stems from feelings directed at Gavin, which is curious because our characters are quite different.”

Gentry understands Casalegno, 25, who is navigating his own experience in the show’s third and final season. “I know what it’s like to hear people say, ‘Wow, this guy’s the worst!’”

Like Casalegno, Gentry has learned to deal with the highs and lows of fandom reactions, which can sometimes feel close to home.

“The nature of this job makes it very personal. At the end of the day, it’s my identity. I saw someone comment when the [season 2] trailer came out, ‘No matter how attractive Alex gets, I can’t find him appealing because he’s 5’7 in real life.’ That’s their opinion, but have you never heard of the short king theory?” he joked. “The way I present myself is how I present myself. Negative feedback sticks with me longer. When people criticize Alex, it’s a bit more acceptable since my role is to reflect both his flaws and strengths.”

Gentry acknowledges that fan feedback is part of the process, but admitted that the intense divisions into relationship ‘teams’ in shows like MLWTWB were foreign to him prior to joining the cast.

“I’ve never seen The Vampire Diaries, and I’m not into that world, but people are very passionate about their alliances. I didn’t realize how much people rally behind their chosen characters,” he added, highlighting that fandom culture can be both “toxic” and “humorous,” especially since the narrative is predetermined before release.

“It’s not Love Island. Everything is scripted,” he said with a grin.

Yet Gentry admits it’s not always easy to disregard the noise. “Intellectually, I know that it’s not me, but rather the character I’ve created,” he stated. “Nonetheless, Alex’s heartbreak resonates deeply with me. His emotions are rooted in mine.”

Gentry’s connection to Alex has deepened while filming seasons 2 and 3, currently in production. “I’ve come to realize that I internalize the story more than I initially thought,” he observed. “I believe Alex is on three distinct journeys each season, and with each experience, I, Ashby, evolve and notice differing emotions.”

Alex’s most vulnerable experiences often leave him rattled. Gentry recounted filming the climactic moment of season 1 when Jackie kissed Cole behind Alex’s back. “It genuinely hurt me; I felt it deeply. While filming, all emotions are authentic,” he shared. “When I told her I loved her, and she didn’t reciprocate, that was real pain — as Ashby. The feelings are genuine, despite the fictional narrative.”

However, it’s this complexity that makes the experience rewarding. Although Alex may not always win the girl, he embodies depth, vulnerability, and humanity beyond the romantic entanglements. This is especially evident in season 2, where Alex emerges from a transformative summer in Montana, both physically and emotionally.

The trailer for season 2 marks a pivotal shift in public opinion about Alex, particularly due to his “glow up,” which showcases new outfits, a fresh hairstyle, and a sun-kissed glow.

Gentry expressed that he anticipated Alex’s physical transformation in the second season, aligning closely with the writers’ vision: “That’s a classic trope — getting hot post-breakup,” he explained. “I was intrigued by exploring this new facet of Alex. In season 1, I interpreted him as the less conventionally attractive brother.”

He further elaborated, “During the audition for the pilot, I was told, ‘You aren’t like Cole; he’s the conventional charmer. He’s the marble statue.’ I even shared this analogy with our costumer: ‘He’s the marble sculpture while I’m the cartoon stick figure.’ It wasn’t meant negatively; I saw both as attractive in different ways — one fitting a mainstream standard while the other exudes a more unique, alternative charm.”

Gentry disclosed that he actually altered his physicality more for season 1 than for the upgraded version of season 2, saying, “I lost weight and avoided the gym. Prior to filming season 1, I was in great shape, but I adjusted my routine because it didn’t fit Alex’s character, who is less athletic than Cole. Cole is the athlete; Alex is the bookworm.”

He even altered “how I walk and speak,” and applied more product to his hair. “The physical transformation for season 2 was essentially a reflection of my everyday life,” he added with a chuckle, “I wish someone had told me, ‘Don’t stress, Ashby; you’ll always finish second!’”

Although it’s heartening to see fans slowly gravitating towards Team Alex in season 2, Gentry wishes for viewers to appreciate Alex’s character beyond mere looks.

“I want to express this tactfully but truthfully,” he confided. “Upon viewing the [positive] reactions to Alex in the trailer, my thought was, ‘Don’t just choose the boy based on his looks!’ There is so much more to a relationship than physical attraction. Of course, attraction matters, but when fans say, ‘I’m switching teams,’ I hope they grasp the deeper essence.”

Choosing Alex based solely on appearance may not pose an issue for most viewers. While season 1 hinted at Alex’s conflicted feelings towards Jackie, season 2 establishes his sincere intentions. Not only does he forgive Jackie for cheating with his brother and disappearing to New York, but he also desires to rekindle their romance — only to surprise her with her confession of love for Cole once more.

Gentry admitted that Alex’s readiness to forgive and forget was unexpected yet intriguing for him as an actor. “Reading the script, I was astonished, ‘Are you serious?’ But the challenge is to embrace that. People often say, ‘You must like your character,’ but I entirely disagree. Disliking aspects of your character is fair; understanding their motivations is what matters. Season 2 pushed me to explore this complex emotional terrain, not only due to the physical transformations but also in navigating the fractured relationship with Jackie, which personally, I would struggle with.”

Yet, he perceives Alex’s affection as genuine; he is resolute that their connection could work.

“He recognizes something with Cole but is unfazed,” Gentry explained. “That’s what distinguishes me from Alex; he is willing to love her openly, while I wouldn’t pursue someone interested in another. Alex, however, simply loves Jackie and deeply desires her. It’s less about rivalry with Cole and more about mutual mistakes — he just wants to be with her.”

He also doesn’t cast blame on Jackie for her actions, believing she has her feelings for Alex, albeit in her own manner. “Jackie loves Alex; I don’t doubt that. However, she’s in love with Cole,” he contemplated. “I believe she does care for Alex.”

Regarding season 3, Gentry remains tight-lipped: season 2 concludes without Alex reacting to Jackie and Cole’s revelations before the credits roll. What he is willing to divulge is that he “didn’t anticipate” what’s to follow, hinting that some unresolved romantic threads from season 2 may linger.

“Does anything ever truly fade away with anyone?” he mused. “I think not.”

My Life With the Walter Boys season 2 is now streaming on Netflix.