What Meghan Markle's Exes Have Said About Her

Sure, Meghan Markle was already a famous actor before becoming a duchess, but her marriage to Prince Harry shaped her into one of the most recognizable people in the world. The pair was splashed across global headlines following their 2018 wedding, and again in 2020 after announcing their decision to step down as working members of the royal family.

When the Duke and Duchess of Sussex relocated stateside, fans continued to dissect Harry's fractured relationship with his father and brother, at times even blaming Meghan for the perceived familial schism. Unfortunately for the couple, the scrutiny on their marriage just seemed to keep intensifying after they decided to blaze their own trail. "It's been a challenging time," a source told Us Weekly in August 2023. That said, Harry and Meghan continue to put on a united front. "Their relationship has challenges, but they are 100 percent committed to making their marriage work," the insider added.

With all the attention on their marriage, we can't help but think back to Meghan's previous relationships and what went wrong. Unlike Harry, the former "Suits" star was married once before — to film producer Trevor Engelson — and the breakup wasn't amicable. According to the Mirror, Engelson was reportedly "blindsided" by Meghan's request to divorce, and it took him years to get over her. "He's a good guy but Meghan crushed him when she demanded a divorce," the source explained. Here's what Engelson and Meghan's other exes had to say about her.

Meghan Markle met Trevor Engelson in 2004 and the pair was together for nearly a decade, even tying the knot in 2011. But once Meghan's acting career took off and she relocated to Canada to film "Suits," the distance reportedly put a strain on the relationship (via the Mirror). By 2013, it was over for good. In the book, "Meghan: A Hollywood Princess," biographer Andrew Morton wrote that Engelson "could barely contain his anger" when Meghan returned her engagement and wedding rings in the mail. The move had him feeling like "a piece of something stuck to the bottom of Meghan's shoe," and it didn't sit well with the estranged couple's friends, either. Ninaki Priddy, who had been the maid of honor at the Engelson-Markle wedding, was so horrified by her former bestie's actions that she reportedly no longer wished to "associate herself" with Meghan.

Since Meghan skyrocketed to international fame after marrying Prince Harry, there's been talk of Engelson releasing a tell-all memoir about the "years of hell" with his ex, touching on everything from "claims of an emotional affair" to "temper tantrums," per Life & Style. Apparently, Meghan changed completely after landing her breakout gig on "Suits." As a source told Woman's Day (via the Mirror), "Their split was sudden and so ruthlessly done" that Engelson "felt used" by Meghan. It's probably a chapter both Engelson and Meghan would like to put to bed for good.

Though not technically an ex, English footballer Ashley Cole and Meghan Markle made headlines for a potential love connection shortly after she split from Engelson. In 2013, the Daily Mail reported that Meghan had asked around about Cole, who'd "been trying really hard" to reach out to her. Meghan was warned about his notorious infidelity and that was that. But Ashley's brother, Matty Cole, took offense to the story. "It's nonsense, completely made up. [Ashley] definitely wouldn't have to beg Meghan Markle for a date," Matty told The Sun. "She's not the kind of girl he goes for anyway, and he's never fancied her."

In 2019, Ashley himself appeared to address the rumors around his infidelity, and more indirectly, around Meghan. "I'd say I've grown up," the ex-Chelsea defender told The Telegraph. "I was a young, angry kid at the time and now I've grown up and understand the things I did is life, it happens." Ashley went on to share that he has learned from his mistakes, and is happy with his choices. "These are the things I focus on now — my kids and my girlfriend," he added. "It's a different me, I'm more of a family man now."

Matt Cardle was crowned the winner of "The X Factor" in 2010, but he didn't catch Meghan Markle's eye until 2015. In fact, he'd just made his musical debut in "Memphis" when the future royal started following him on social media and they struck up a conversation. To hear Cardle tell the story, it was never a full-fledged relationship. "It was so little then and if not nothing now," the singer told ITV in 2019 (via the Daily Mail). "Yeah, like I say it was nothing, it was absolutely nothing. It's quite funny how something can be made up from nothing."

A year later, Cardle elaborated on their flirtation, explaining that it was a brief dalliance before both he and Meghan settled down with their current partners. "It was just a very weird situation — very odd. And I really don't know how it came about," he shared with The Sun. "Life's got a course and I was not on that one. I've laughed about it, but it's amazing thinking back."

Once Cardle met his girlfriend Amber Hernaman, he knew she was special and immediately cut ties with Meghan. "He met [Amber] 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," a source dished (via Good To Know).

The timing of Meghan Markle's relationship with restaurateur Cory Vitiello is a little murky, but biographer Tom Bower wrote in his book "Revenge: Harry, Meghan and the War Between The Windsors" (via Newsweek) that love was in the air beginning in the summer of 2014. That July, Bower noted that Meghan and the cast of "Suits" dined at Vitiello's restaurant in Toronto. Meghan later gushed over Vitiello in her now-defunct lifestyle blog, "The Tig." Bower wrote, "Shortly afterwards, Vitiello ended a relationship and started to date Meghan. Together they rented a three-bedroomed home in the city's Annex district."

Bower also claimed there was overlap in Meghan's relationships with Prince Harry and Vitiello, as the actor was still living with Vitiello when she was set up on a blind date with the Duke of Sussex. Per The Sun, Vitiello said, "I can't comment on that," responding to a question about whether he and Meghan split because of Prince Harry. However, that does seem to be the case. Prince Harry is believed to have flown out and visited Meghan in Toronto in July 2016, while she and Vitiello were still together. Apparently, Vitiello was "relieved" when Meghan initiated the split because "the final months [together] had been unpleasant" (via Page Six).

When Fashion magazine caught up with Cory Vitiello in March 2018, he refused to take any bait from an interviewer who kicked off their convo by fishing for Meghan Markle tea. After it was pointed out to him how "crazy" it was that he had a chain of chicken restaurants and Prince Harry had proposed to Meghan Markle while they were roasting a chicken (that's a bit of a stretch, but, sure), the chef shut down that line of questioning by saying, "I appreciate the respect and privacy on both ends."

Vitiello's cooking came up again the following month when his mother spoke to the Daily Mail. She expressed skepticism over a rumor that Meghan had told dinner guests that the pasta they were eating was her recipe when it was actually her then-boyfriend's. The Daily Mail didn't get Vitiello to confirm or deny this rumor, but the outlet did get him to weigh in on its conclusion that Meghan improved her social status by dating him. '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 said. He also refused to say which party had done the dumping, stating, "I'll let the public forum debate that!"

Like many of Meghan's other exes, Vitiello likely disappointed the Duchess of Sussex's haters by giving them no ammo to use against her. On the contrary, he described himself as her "friend" and said of her new life, "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."

Like many of Meghan Markle's exes, her college boyfriend, Steve Lepore (pictured above), has avoided kicking the hornets' nest by sharing any intimate details about their relationship with the press. However, Radar did score a brief comment from him after Meghan and Prince Harry got engaged in 2018. He wished the couple well, saying, "Best of luck to her and Prince Harry."

Before she started scoring TV roles regularly, Meghan met Lepore in 1999 during her freshman year at Northwestern University. He was on the basketball team and considered a "hottie" by Meghan's sorority sisters, according to Andrew Morton's book, "Meghan: and the Unmasking of the Monarchy." Morton writes that the two had different approaches to college life, with Meghan being a bit of a party girl and Lepore being too focused on his budding athletic career to join her on her weekend outings. But what reportedly ended their relationship was Lepore transferring to another school. His hard work paid off, as he was named associate head coach of Eastern Kentucky University in 2025.

Going back a little further in her romantic history, one of Meghan's high school boyfriends, Luis Segura, told Daily Mail Weekend that he didn't want to say too much about her out of respect for her privacy, but did state that they had some "good times" together. "She's great, and was always a wonderful actress," he added. Segura is now a real estate agent, and when he spoke to the publication in 2018, he and Meghan were reportedly still keeping in touch with each other.

One of the exes who has had the most to say about Meghan Markle is one of her earliest boyfriends. In a 2013 appearance on "Larry King Now," Meghan revealed that she was 13 years old when she had her first kiss at summer camp. "And I kissed him," she said. The recipient of the smooch was Joshua Silverstein, who later became a pro beatboxer and showcased his skills on the show "Drop the Mic." On "Lorraine," Silverstein revealed he and Meghan didn't just kiss but had a brief teenage romance. "She told her friends she liked me; I told my friends I liked her," he said of how they became a couple.

Silverstein had a lot of praise for his ex, calling Meghan "courageous" for opening up to Oprah Winfrey about her most painful experiences as a royal. He also called out the royal family for its "history of racism" and lauded Meghan for speaking out about the racist behavior she said she witnessed firsthand. "The fact that Meghan is going to get on TV and bravely talk about that is awesome," he said.

After Meghan was accused of bullying royal staff members in 2021, Silverstein told Us Weekly he gave no credence to the claims and argued that Meghan's behavior had been misconstrued. "When you find women of color — particularly Black women — standing up for themselves and speaking out and speaking against what they feel [is] disrespect or oppression, often times whiteness tends to classify that in negative ways because they don't want that to happen," he said. Silverstein guessed that the royals didn't exactly roll out the welcome mat for Meghan, suggesting that she was just doing what it took to endure being in that environment.