All The Things Meghan Markle's Exes Have Spilled About Her

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In some people's view, one of the biggest red flags in Prince Harry and Meghan Markle's relationship is Meghan's dating record. Time and time again, royal biographers have perpetuated the idea that the "Suits" alum used to strategically date men to further her social standing. In Tina Brown's "The Palace Papers," she wrote that Meghan's estranged father, Thomas Markle, had told her that, although she could have dated just about anybody in college, Meghan was "always very clear about who she wanted." Thomas was also quoted as saying, "She's very, very effective with men" (via Express).

To make his point, Meghan's father claimed that she had pointed to a man when she was studying at Northwestern University and said that she would date him someday. It goes without saying that Meghan went on to do just that. Additionally, according to The Sun's relationship expert, Annabelle Knight, the future royal had used her college romance with the popular basketball player Steve Lepore to give herself a social boost amongst her peers. "It feels as though Steve was used as a currency for Meghan's progression, she aimed her sights high and didn't fail to meet her target," Knight said. 

When royal biographer Tom Bower appeared on GB News in July 2022, he claimed that Meghan had even done some in-depth research into Prince Harry before they met so that she could convince him that she was the one. However, based on what most of Meghan's exes have had to say about her, it's safe to say that most of them might not exactly agree with her being characterized as a calculated social climber.

In her freshman year at Northwestern University, Meghan Markle fell for basketball player Steve Lepore. In royal biographer Andrew Morton's "Meghan and the Unmasking of the Monarchy," he claimed that the relationship did wonders for Meghan's relationship with her Kappa Kappa Gamma sorority sisters, most of whom were impressed that she had managed to court an attractive man like Lepore. Additionally, in 2019, a source informed The Sun that Meghan would also regularly gush about her beau's looks, taking particular pride in his well-built chest. 

They also claimed that dating a star basketball player was an entirely different experience for someone like Meghan, who was used to hogging the spotlight. In Morton's book, he wrote that their relationship also faced some friction because the future Duchess of Sussex was all about partying it up in those days, while Lepore was razor-focused on his basketball career. Alas, the future royal's first serious adult relationship ended after only five months because the basketball player transferred to a different college.  

According to a Star Magazine insider, Meghan was quite "heartbroken" following the end of her relationship with Lepore (via RadarOnline). The source further divulged, "He wasn't royalty, but to have your first real, adult romance end suddenly, that's something that stays with you." On the outside, it's obvious that they have both moved on completely. According to EKUSports, Lepore is married and has two daughters. As a result, it's unsurprising that he didn't have much of a reaction to his ex-girlfriend's engagement to Prince Harry in 2018, telling RadarOnline: "Best of luck to her and Prince Harry."

After a 7-year courtship, Meghan Markle married Trevor Engelson in 2011. Despite that seemingly solid foundation, the couple ended up parting ways after only two years of marriage, citing "irreconcilable differences" in their court filings (via Business Insider). In Andrew Morton's 2018 book "Meghan: A Hollywood Princess," one insider claimed that Engelson was completely blindsided by his first wife's decision to end their marriage. Ninaki Priddy, the Duchess of Sussex's ex-best friend who was also her first maid of honor, similarly stated that she was under the impression that Meghan and Engelson were finding their way through their marital issues.

According to Priddy, she had cut off all ties with the royal after learning Engelson's version of why their marriage ended. One confidant even claimed that the producer eventually started "feeling like he was a piece of something stuck to the bottom of [Meghan's] shoe" (via Express). Meanwhile, in Tina Brown's "The Palace Papers," she claimed that Engelson had felt "used" by his first wife and had even told people that she had returned their wedding band and engagement ring through the mail (via Daily Mail).

As for Engelson himself, he has remained entirely tight-lipped about his marriage to Meghan. However, the producer's ex, Bethenny Frankel, publicly claimed that he had made a somewhat shady comment about his first wife. During a November 2025 appearance on "The Toast," the "RHONY" alum claimed that she had asked Engelson if Meghan would "close" the deal with Prince Harry. In response, he had supposedly said, "'Oh, she'll close." With that little tidbit, it appears that Engelson might have felt that marriages were more like business deals to his ex-wife.

In Tom Bower's 2022 book "Revenge," he shared that Meghan Markle began dating Cory Vitiello after dining at his restaurant with her "Suits" castmates in July 2014. At one point, their relationship was serious enough that they moved into a rented 3-bedroom apartment together. According to Bower, Meghan and Vitiello's relationship was basically done and dusted by the time she went on a blind date with Prince Harry. 

However, they hadn't officially called it quits, and the chef was still supposedly residing in their shared home while initial sparks flew between Harry and Meghan. Ultimately, the "Dater's Handbook" actor had reportedly only had the all-important talk with Vitiello after going on a blind date with the royal and seeing him for about a week. According to Bower, Meghan hadn't initially made her now ex-boyfriend aware of her connection with Harry.

Despite all that, the restaurateur has publicly maintained that they ended on good terms. When the Daily Mail tried to get him to spill the tea on whether or not Meghan used him to climb up the social ladder during an April 2018 chat, Vitiello replied, "I've got a lot of respect for Meghan and, from my end, to make it seem like I'm part of the story [of her elevation into the ranks of royalty] would seem self-serving and opportunistic." He also gushed about his ex-girlfriend, saying, "I'm pleased for Meghan. She's a great girl. There is no bitterness. ... Meghan's a wonderful girl, and I'm very proud of her." It was obvious that he valued Meghan's privacy, because he stayed mum when asked who had wanted out of their relationship more.

In May 2019, a confidant informed The Sun that Meghan Markle had a bit of an online fling with Matt Cardle, who notably won "The X-Factor" in 2010. It is all believed to have started in 2015, when the ex-contestant followed the actor on Instagram after recognizing her from "Suits." However, Cardle was in for a pleasant surprise as Meghan not only followed him back but also slid into his DMs with a message about admiring his music. 

After they exchanged messages for a short while, Meghan asked him if he would like to meet IRL. For better or for worse, things didn't go much further than that, as the source explained, "He met his girlfriend and knew it wasn't appropriate to keep talking to Meghan, so he ended up ghosting her ... He didn't reply to her last message." Needless to say, finding a new partner isn't an instance of when it's okay to ghost someone. According to the source, their connection could have very well been a case of the right person, wrong time. 

However, Cardle publicly maintained that his metaphorical crossing of paths with Meghan was no big deal at all. In fact, during a 2019 appearance on iTV's "Lorraine," he said, "It was absolutely nothing. It's quite funny how something can be made up from nothing" (via News.com.au). Meanwhile, in a December 2020 chat with The Sun, he claimed that the speculation surrounding his connection with Markle was "very odd" and something that seemingly sprang up out of nowhere. Overall, he found the whole ordeal quite laughable.

In Andrew Morton's "Meghan: A Hollywood Princess," he wrote Meghan Markle's first serious relationship was with classmate Luis Segura while they were in high school. According to Morton, Segura had deemed his ex-girlfriend "sweet and fun" (via Express). Those words could also be used to describe Meghan's teen romance, which came to an end after two years. During an April 2018 chat with the Daily Mail, Segura made it clear that he looked back on his relationship with Meghan fondly, saying, "I'd like to talk about our good times, but she's a very private person and it's a big deal with the royals. But she's great, and was always a wonderful actress." 

Another one of Meghan's beaus from school, Joshua Silverstein, similarly appeared to have nothing but admiration for her. During a May 2021 appearance on "Lorraine," Silverstein revealed that his friend group and Meghan's friend group had nudged them towards each other after learning they were both crushing on each other. The beatboxer also revealed that they split up right before they entered high school and remained on good terms afterward. 

When asked to share his feelings about Meghan's marriage to Prince Harry, Silverstein said, "I hope she's happy." Later on, he also stated that his ex-girlfriend and the royal made "an amazing couple." Silverstein couldn't help but appreciate Meghan and Harry for working with Oprah Winfrey to create a Netflix series that would shine a light on mental health issues. Suffice it to say that Meghan and Silverstein know all about how to have a successful friendship with an ex.