Signs Lauren Sánchez & Jeff Bezos Are Becoming Don Jr. & Kimberly Guilfoyle 2.0

One of the many strange things about Jeff Bezos and Lauren Sánchez's relationship is the fact that it shares lots of common ground with Donald Trump Jr.'s failed engagement to Kimberly Guilfoyle. Initially, both couples tried their best to convince everybody that their respective relationships were going swimmingly. For Valentine's Day 2022, the former Fox News host wrote Don Jr., whom she had been dating since 2018 by then, a short and sweet Instagram tribute. "Falling in love with my fiancé more and more every day," Guilfoyle penned while simultaneously confirming their engagement. "You're my best friend, my support system and my forever guy." 

Likewise, the Amazon founder and Sánchez also put on an equally loved-up display in the initial years of their romance. During a 2023 Wall Street Journal interview, Sánchez gushed, "We love to be together and we love to work together." She continued by proudly listing, "We fly together. We work out together. We're together all the time." Additionally, she shared that despite Bezos' demanding schedule, he still made her Betty Crocker pancakes every Sunday. 

The tech billionaire popped the question in 2023, four years after they first made their relationship public. On the other side, Don Jr. and Guilfoyle weren't faring as well since they parted ways in late 2024, and he wasted no time finding love with socialite Bettina Anderson. Although these relationships seem quite different on paper, they actually share a lot of the same red flags that lead us to believe that Bezos and Sánchez's relationship might not last either.

In 2022, an insider informed the Daily Mail that Donald Trump Jr. had popped the question to Kimberly Guilfoyle on his birthday, on New Year's Eve 2020. In an exclusive chat with The List, a diamond expert weighed in on the price tag of Guilfoyle's engagement ring from Don Jr. Olivia Landau, a 4th-generation diamond expert, a G.I.A. Graduate Gemologist (GG), and the founder and CEO of The Clear Cut, took a closer look at the massive rock and estimated that it would've made his pockets about $65,000 to $250,000 lighter. 

At the time, that eye-watering number led everyone to believe that Don Jr. couldn't have been more serious about his commitment to the former Fox News anchor. However, time told a different story because the celebrity couple didn't have any details of their big day locked down right up until their eventual split in December 2024. And sadly, Jeff Bezos and Lauren Sánchez seem to be faring similarly. While speaking to Vogue in December 2023, the helicopter pilot proudly declared that her beau popped the question in May.  

Similar to Don Jr., the Amazon founder spared no expense with the ring, going all out with a rare pink diamond. But as the years passed, they didn't seem to be making great strides with their wedding plans. However, in March 2025, a source confirmed to the Daily Mail that Sánchez and Bezos had set things in motion for a summer wedding. But it's worth noting that we heard a similar tale of them holding their nuptials in December 2024, which ultimately proved to be false.

In the months preceding Kimberly Guilfoyle's and Donald Trump Jr.'s split announcement, she shared some strange social media posts that made it abundantly clear that they had drifted apart. The media personality essentially stopped sharing any Instagram photos of just the two of them after June 2024. In the following months, Guilfoyle's social media posts made her seem like the queen of deflection because she continued to gush about Donald Trump while only posting awkward group photos with her fiancé. Lauren Sánchez has similarly made several Instagram posts that caused us to question if her relationship with Jeff Bezos was really thriving. 

For instance, Sánchez's 2025 Valentine's Day post accidentally revealed that her romance with Bezos may be running dry. The bestselling author shared an Instagram Story of her fiancé sitting at a desk and only wrote alongside it "Happy Valentine's Day my love," per People.  A few days prior, Sánchez added a rather cryptic caption to another photo of her in a helicopter: "Some years start with turbulence, but that's just the wind reminding you to spread your wings." Needless to say, the two posts could point to trouble in paradise for the celebrity couple. 

Further, the dry Valentine's Day tribute seems even more suspicious when we consider how much she gushed about Bezos for his birthday in January 2024. "Today is another day where your laughter fills our home, and that smile of yours lights up every room. Wishing you an abundance of simple joys and quiet moments of happiness," she wrote in a heartfelt Instagram tribute at the time. 

Shortly after Jeff Bezos and Mackenzie Scott shockingly announced the end of their 25-year marriage in January 2019, The National Enquirer shared explicit messages that the Amazon founder had purportedly sent to Lauren Sánchez. "I love you, alive girl. I will show you with my body, and my lips and my eyes, very soon," a then-married Bezos wrote in an April 2018 text, per Page Six. It's worth noting that Sánchez was also technically married to Patrick Whitesell at the time of the flirty text exchanges. 

According to a People source, though, the journalist and Whitesell's marriage had lost its spark around 2016, and they were living entirely separate lives. However, Sánchez and Whitesell only filed divorce papers to end their 14-year marriage in April 2019. Kimberly Guilfoyle and Donald Trump Jr.'s relationship stemmed from a similarly shaky past. In March 2018, a few days after Vanessa Trump, Don Jr.'s wife of 12 years, filed for divorce, Page Six reported that he had cheated on her with singer Aubrey O'Day. 

Insiders dished that the alleged infidelity occurred shortly after Don Jr. first laid eyes on O'Day on the set of "The Apprentice" back in 2011. The president's eldest son reportedly "pursued [Aubrey]" and "He told her that his marriage was already in the process of dissolving." However, Vanessa was actually pregnant with their third child, Tristan, around the same time. Insiders also claimed that the mother of Don Jr.'s five kids was completely heartbroken when he confessed that he wanted to end their marriage for O'Day.

Lauren Sánchez and Kimberly Guilfoyle notably come from similar professional backgrounds. While Guilfoyle appeared in several Fox News shows for over a decade, Sánchez worked for KTTV's Fox 11 News. However, that's not the only thing the two women have in common. They also share a deeply rooted love of sexy, borderline inappropriate outfits. In January 2025, Sánchez made headlines when she wasn't afraid to show skin at Donald Trump's inauguration (and Mark Zuckerberg took note). 

Although the helicopter pilot tried to stay in line with the formal theme by donning a white blazer, she completely derailed the look by only wearing a lacy bra top underneath it. To make matters worse, Sánchez has worn several outfits that are far more inappropriate than her inauguration day look. And Guilfoyle has been in the same boat numerous times. For instance, when the media personality visited the Trump National Golf Club Jupiter in November 2023, she donned a tightly fitted hot pink dress with a plunging neckline that didn't leave much to the imagination. 

However, Guilfoyle served up her most inappropriate look in a bizarre cooking video in September 2024. Although she set out to share a recipe for lamb chops, it was difficult to focus on anything she was saying because our minds quickly wandered off to try to make sense of her bizarre decision to wear a strapless floral dress instead of something more casual and fitting for the homely environment of the shoot. 

Forbes estimates that Jeff Bezos' net worth is somewhere in the region of a whopping $209 billion, and his lifestyle with Lauren Sánchez reflects it. In addition to owning several multi-million-dollar properties and private planes, the Amazon founder is also the proud owner of a luxurious super yacht, which came with an insanely large price tag of $500 million. Of course, he also doesn't spare any expense when showering his beloved fiancée with gifts either. During a 2024 chat with People, jewelry expert Briony Raymond estimated that the engagement ring he gave Sánchez was a 30-carat cushion-cut diamond that would have cost him at least $3 million and possibly even exceeded $5 million. 

According to Celebrity Net Worth, Donald Trump Jr. is worth an eye-watering $350 million, so he doesn't hold back when it comes to splurging on the finer things in life either. However, his and Kimberly Guilfoyle's interests were more peculiar than the average multi-millionaire. In 2019, an insider disclosed to the New York Post that the celebrity couple had bought a $4.4 million mansion in the Hamptons. Although the lavish 7-room property would have been enough to win most people over, Don Jr. apparently had a strange need that no ordinary home could fulfill. 

"One of the first questions Don Jr. asked was where he could store his guns," the insider divulged. Of course, the property didn't have that so-called amenity, so the couple decided to build an eighth room to serve this very specific purpose. Of course, Guilfoyle and Don Jr. also had the benefits of Donald Trump's luxurious properties and his private plane too.