Fresh off one of the biggest moments of his career, Timothée Chalamet didn’t head to another red carpet or press junket.
Instead, he slipped away to Cabo San Lucas with Kylie Jenner for a sun-soaked break that felt worlds away from awards season chaos.
The timing was telling — the trip came just a day after Chalamet secured his third Oscar nomination, making the getaway feel both celebratory and deeply personal.
Keeping It Cozy by the Water
The famously private pair were spotted at a secluded waterfront property, where the mood was relaxed and unmistakably intimate.
They lounged outdoors overlooking the water, sticking close as they chatted quietly and took in the scene.
Nothing flashy, nothing staged — just two people clearly comfortable in each other’s space.
Kylie’s Effortless Cabo Style
Jenner leaned into vacation mode, showing off her toned figure in a black triangle bikini top paired with loose black pants.
At one point, she casually wrapped a sweatshirt around her waist while scrolling through her phone poolside.
Her dark hair was slicked back, her look makeup-free, and the whole vibe screamed easy, unfussy luxury rather than glam spectacle.
Timothée’s Go-To Off-Duty Look
Chalamet matched the laid-back energy, opting for a black long-sleeve shirt, dark pants, and a camouflage baseball cap.
He often walked just behind Jenner, hands tucked into his pockets, quietly attentive and clearly at ease.
Observers noted how he stayed close, chatting softly and never straying far from her side.
From Dockside Strolls to Life on the Water
Later, the couple took a stroll along the dock before boarding a sleek luxury boat.
Once onboard, they appeared relaxed and familiar with the crew, blending in easily rather than demanding attention.
At one point, Jenner wore a black face mask and carried a large tan tote as Chalamet leaned in close, the two sharing what looked like a private conversation, seemingly oblivious to anyone else around them.
Quiet Moments Speak the Loudest
Not every moment was shared together. While Jenner answered messages on her phone, Chalamet took some time to himself, journaling quietly nearby.
The contrast felt intimate rather than distant — a snapshot of a couple comfortable enough to coexist without constant conversation.
A Rare Public Date the Night Before
The Cabo sighting followed a rare public date night just hours earlier.
According to TMZ, the couple celebrated Chalamet’s Oscar nomination with a long dinner at Flora Farms, a beloved celebrity hotspot.
An eyewitness said they spent over an hour laughing, chatting, and staying fully engaged with one another throughout the meal.
Smitten, Even Without the PDA
While there were no over-the-top displays of affection, the source described the pair as “totally into each other,” noting that Chalamet appeared especially smitten.
At one point, he was seen snapping photos of Jenner with a digital camera and reviewing the shots while she scrolled through her phone beside him.
Despite the packed restaurant, most diners were reportedly older and didn’t recognize the A-list duo.
A Place Hollywood Loves
Flora Farms has long been a favorite for celebrities seeking low-key luxury.
Adam Levine and Behati Prinsloo famously married there in 2014, and stars like Busy Philipps have also been spotted enjoying the venue — making it a fitting choice for a discreet celebration.
More Serious Than Fans Realized
The romantic escape came just days after reports revealed the couple had quietly traveled together even before the nomination news broke.
Earlier this month, a source told Page Six that Jenner and Chalamet have been living together in Los Angeles for over a year and behave “like they’re basically married already.”
“They’re obsessed with each other and always together,” the insider claimed, adding that Chalamet has become involved in the lives of Jenner’s children, Stormi, seven, and Aire, three, whom she shares with ex Travis Scott.
Awards Season Love Letters
This trip also followed a series of very public acknowledgments from Chalamet during awards season.
At the Golden Globes, he referred to Jenner as his “partner” in his acceptance speech, telling the audience, “To my parents and partner, I love you.”
Weeks later, while accepting Best Actor at the Critics Choice Awards, he doubled down.
“Thank you to my partner of three years,” he said.
“Thank you for our foundation. I love you. I couldn’t do this without you.”
Jenner was seen mouthing back, “I love you too,” before the couple shared a kiss.
From Rumored Split to Solid Front
The affectionate moments stood in stark contrast to reports late last year suggesting the relationship had cooled.
In November, a source claimed the couple were in a “cool-down cycle,” describing them as on-again, off-again rather than fully broken up.
“They cool down and they heat up,” the insider said at the time.
What the Experts Say
Psychologist Darren Stanton previously noted that the couple’s recent public closeness sends a clear message.
“They’re showing the relationship is real, secure and intentional,” he explained, adding that the timing of their appearances seems carefully considered amid intense media scrutiny.
Relationship psychologist Dr. Kathy Nickerson echoed that view, pointing out that celebrity couples function as brands as much as partners.
“When a high-profile relationship appears stable and affectionate, it reassures fans and partners alike,” she said.
“Visibility often works as reassurance signaling.”
Privacy Still Comes First
Despite the increased attention this awards season, Jenner and Chalamet continue to keep their romance largely off social media and out of interviews.
Both have repeatedly emphasized how important privacy is to them — Chalamet has said he “will not talk about” the relationship, while Jenner has stressed that keeping parts of her life private is “so important.”
What Comes Next?
With awards season still unfolding and their Cabo retreat now behind them, all eyes are on what’s next for Hollywood’s most quietly compelling couple.
If this trip was any indication, they’ll continue doing things their own way — close, intentional, and just out of the spotlight enough to keep everyone guessing.
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