Note: We’re revisiting this story, which originally made headlines in December 2024.
Even being the granddaughter of a U.S. president doesn’t protect you from classic family embarrassment.
In a candid YouTube Q&A, Kai Trump — daughter of Donald Trump Jr. and Vanessa Trump — shared a cringeworthy moment from a day on the golf course with her grandfather, former President Donald Trump.
Trump’s Teasing Leaves Kai Blushing on the Green
According to Kai, what started as a fun family outing quickly turned awkward when her grandfather made a playful comment that left her mortified. While she laughed it off during the Q&A, she admitted it was one of the most embarrassing moments she’s ever experienced with him.
Note: We’re revisiting this story, which originally made headlines in December 2024.
Even when your grandfather is a former U.S. president, you’re not safe from a little family embarrassment.
Kai Trump Reveals Her ‘Most Embarrassing’ Moment With Grandpa Donald on the Golf Course
President Donald Trump may be known for his bold personality—and according to his granddaughter Kai, that charisma can sometimes lead to hilariously awkward moments.
While answering fan questions during a recent YouTube Q&A, Kai, the daughter of Donald Trump Jr. and Vanessa Trump, opened up about a cringeworthy experience she had with her grandfather on the golf course.
“My most embarrassing moment with my grandpa was when I brought one of my guy friends to play golf,” Kai shared. “Right away, he goes, ‘Oh my God! Look how handsome your boyfriend is!’”
The unexpected comment left Kai visibly flustered.
“I was so embarrassed because, like, he has a girlfriend,” she added with a laugh. “That was just awkward. That’s my most embarrassing moment ever.”
Another Cringe—But This Time, She’s Staying Quiet
Kai also teased another awkward moment involving her grandfather meeting a guy she had been talking to—but this time, she chose to keep the story to herself.
“I won’t even get into that one,” she said, hinting that some memories are best left off the internet.
Photo Credit: President Trump posing with his granddaughter Kai on the golf course, via @kaitrumpgolfer / Instagram
Note: We’re revisiting this story, which originally made headlines in December 2024.
Kai Trump Spills on Her Most Embarrassing Grandpa Moment—And the Life Lesson She’ll Never Forget
Being the granddaughter of a former (and current) U.S. president might sound glamorous—but as Kai Trump proves, it comes with its own share of awkward family moments.
In a recent YouTube Q&A, Kai, daughter of Donald Trump Jr. and Vanessa Trump, gave fans a rare peek behind the curtain of life with her famous grandfather, former President Donald Trump. And yes—there were some cringe-worthy laughs along the way.
“Look How Handsome Your Boyfriend Is!”
One of Kai’s most memorable stories took place on the golf course, where Trump’s larger-than-life personality stole the spotlight.
“My most embarrassing moment with my grandpa was when I brought one of my guy friends to play golf,” she recalled. “Right away, he goes, ‘Oh my God! Look how handsome your boyfriend is!’”
The unexpected remark left Kai visibly mortified—especially since, as she quickly clarified, “He has a girlfriend!”
Laughing it off, she added, “That was just awkward. That’s my most embarrassing moment ever.”
Another Mystery Moment She’s Not Ready to Share
And that wasn’t the only time Grandpa Trump caused a little embarrassment.
“He embarrassed me again when he met a guy I was talking to,” Kai teased. “But I’m not telling what happened there.”
Whatever happened, she’s clearly keeping it under wraps—at least for now.
A Granddaughter’s Admiration for Her Grandfather
Despite the occasional awkward moment, it’s clear that Kai holds deep respect for her grandfather. During the Q&A, she reflected on one of the biggest life lessons she’s learned from him.
“He’s taught me to never give up,” she said. “If I have a dream, always try to achieve that dream and never stop trying, because one day, it will happen.”
She then pointed to his unlikely return to the White House as proof of that message.
“He’s president of the United States again, so never give up on your dreams!”
Kai’s Celebrity Crush? She’s Got Outer Banks Fever
In a lighter moment, Kai let fans in on her current celebrity crush—and it turns out she’s a big fan of Netflix’s hit show Outer Banks. Though she didn’t name names, fans were quick to guess she might be talking about heartthrob Chase Stokes, who plays John B.
Kai Trump Gets Candid: Celebrity Crushes, Blushing Moments & a Message to Her Grandpa
Kai didn’t hold back during her YouTube Q&A—from awkward golf course stories to her biggest celebrity crush, the 17-year-old let fans in on all the fun and feels.
Blushing Over Rafe Cameron
While chatting about her favorite shows, Kai couldn’t resist confessing her admiration for one particular Outer Banks star.
At first, she reached for her phone to double-check his name—but quickly laughed it off.
“Why do I need my phone?” she said with a grin. “He is Drew Starkey, and he’s on Outer Banks.”
Starkey, 31, plays the troubled (but undeniably good-looking) Rafe Cameron in the hit Netflix series. And judging by Kai’s reaction, the crush is real.
“Oh my God, I’m blushing now!” she giggled, covering her face.
A Proud Granddaughter After a Historic Comeback
Beyond the laughs and lighthearted moments, Kai also showed her serious side—especially when it came to her grandfather’s recent political triumph.
Following Donald Trump’s 2024 election victory over Kamala Harris, Kai took to social media with a heartfelt message.
“No one works harder or cares more about the American people,” she tweeted, shortly after the results were confirmed.
Now serving as both the 45th and 47th president of the United States, Trump’s historic return to the White House clearly left a strong impression on his granddaughter.
Kai Trump Shares Her Most Embarrassing Grandpa Moment—And the Powerful Lesson She’s Learned from Him
Being the granddaughter of a former—and now current—U.S. president comes with its own set of perks and pitfalls. For Kai Trump, daughter of Donald Trump Jr. and Vanessa Trump, it also means some seriously unforgettable (and awkward) memories with “Grandpa.”
In a recent YouTube Q&A, Kai opened up about everything from cringeworthy family moments to her celebrity crush—proving she’s not just part of a political dynasty, but a rising personality in her own right.
Golf Course Giggles: Grandpa’s Comment That Left Kai Mortified
“My most embarrassing moment with my grandpa was when I brought one of my guy friends to play golf,” Kai shared. “Right away, he goes, ‘Oh my God! Look how handsome your boyfriend is!’”
The moment left her blushing—especially since, as she pointed out with a laugh, “He has a girlfriend!”
But the embarrassing encounters didn’t end there.
“He embarrassed me again when he met a guy I was talking to,” she teased. “But I’m not telling what happened there.”
The Biggest Lesson from Grandpa Trump
Despite the occasional awkward moment, Kai made it clear she has deep admiration for her grandfather—and what he’s taught her about perseverance.
“He’s taught me to never give up,” she said. “If I have a dream, always try to achieve that dream and never stop trying, because one day, it will happen.”
She pointed to his historic political comeback to drive the message home:
“He’s president of the United States again, so never give up on your dreams!”
Celebrity Crush Confession: Blushing Over Outer Banks
Kai also gave fans a peek at her pop culture side—specifically her current celebrity crush.
While thinking out loud, she began to reach for her phone before stopping herself.
“Why do I need my phone?” she laughed. “He is Drew Starkey, and he’s on Outer Banks.”
Starkey, who plays bad boy Rafe Cameron in the Netflix hit, clearly made an impression.
“Oh my God, I’m blushing now!” she admitted, hiding her face as she giggled.
A Heartfelt Message After the 2024 Election Win
Following Donald Trump’s 2024 victory over Kamala Harris, Kai proudly celebrated her grandfather’s return to the White House.
“Congratulations Grandpa, I love you!” she wrote on social media.
She paired the message with a heartwarming family photo from the Trump campaign’s watch party in West Palm Beach, Florida—smiling beside her grandfather and other relatives as they celebrated his historic win.
A Rising Star in the Trump Family
With her mix of humor, authenticity, and clear admiration for her famous grandfather, Kai Trump is carving out her own spotlight—and quickly becoming a standout figure in the next generation of the Trump family.
