How Many Times Has Lauren Sánchez Bezos Been Engaged?

Marrying and divorcing a spouse is one thing Lauren Sánchez Bezos and her current husband Jeff Bezos have in common. The tech billionaire was married to writer and philanthropist MacKenzie Scott for 25 years before they divorced in 2019. Lauren, meanwhile, was married to Hollywood agent Patrick Whitesell for 14 years before they called it quits that very same year. However, a little-known fact about Lauren Sánchez Bezos is that she was actually engaged more than once.

Out of all the men Lauren Sànchez Bezos dated before finding love with Jeff Bezos, she was engaged to five of them. But only two of those engagements — to Whitesell and the Amazon founder — ended in marriage. Sports journalist and radio broadcaster Rory Markas was the first man to make Lauren his fiancée. They met while she was a broadcast journalism intern in L.A. The couple ultimately broke up when she switched jobs, as an insider informed Page Six. She subsequently started dating NFL star Anthony Miller, while he was playing for the Denver Broncos in 1996. 

They were together for a total of four years and engaged for a year and a half before ending things in 2000. Miller told the Daily Mail in 2019 that she forced him to propose and was unfaithful to him, so he eventually dumped her. In 2002, Lauren got with "NYPD Blue" star Henry Simmons, but the couple split in 2004 after being engaged for most of their relationship. She allegedly started dating her now ex-husband Whitesell while still living with Simmons, according to Page Six and E! News.

Finding love after being in relationships that didn't work out is a wonderful thing, but Lauren Sánchez Bezos deals with more judgement than understanding from the public. Although the happy couple got married after knowing each other for six years and dating for at least five of them, famously, Jeff Bezos kickstarted his romance with Lauren Sánchez Bezos in a controversial way. The tech billionaire and helicopter pilot went public before finalizing their respective divorces. The official announcement understandably raised questions about how long they had been dating while still married to other people. Lauren Sánchez Bezos was also plagued by nasty relationship rumors chiefly because of her extensive, and complex, dating history.

Once the news broke, a source dished to Us Weekly, "Patrick [Whitesell] was totally blindsided. He had no idea how serious the affair was or how long it was going on for." They added, "Patrick had no idea she was having an affair with Jeff." Additionally, fellow former fiancé Anthony Miller discussed her supposed infidelity with the Daily Mail that very same month. Other reports on Lauren's love life allude to an overlap between her engagement to Henry Simmons and her relationship with Whitesell.

Although insider sources on the former journalist's side contested what the others said, the rumors still affected her reputation and possibly even caused tension in her marriage to Jeff. However, people judged him for allegedly dating Lauren while still married, so maybe they found common ground on that particular point.