Meghan Markle's dating history includes a basketball player, chef, and a quiet divorce

Prince Harry and Meghan Markle’s romance is only the most recent of Meghan’s relationship past

Meghan Markle and Prince Harry’s royal love story sometimes seems far too perfect, but Meghan has had prior relationships that totally flatlined, including a mysterious divorce

Before marrying Prince Harry, of course Meghan Markle played the field a little bit.

The actress went through plenty of relationships before landing on her Prince charming. In fact, she was even married to another showbiz success story. On the other hand, this is Prince Harry’s first marriage so he definitely had a lot to learn.

Meghan’s relationship history includes some puppy dog love, celebrity connections, and more. We’ve put together a list of those she’s been involved with in the past, including how some of them feel about her current romance. After all, it can’t be easy to see that your ex moved on to British royalty.

Luis Segura

Meghan had a sweet high school relationship ( Image: Getty Images)
Meghan’s relationship history started sweet and innocent like it so often does. Her high school boyfriend was named Luis Segura, according to Andrew Morton’s book, Meghan: A Hollywood Princess. They dated for two years after being set up by his sister. Meghan and Luis had the classic high school relationship, including a date night to prom. However, they split when Meghan became college bound.

Steve Lepore

Steve and Meghan split when he transferred schools ( Image: Getty Images)
It didn’t take her too long to move on as she began dating Steve Lepore during her freshman year at Northwestern University. Steve transferred to Wake Forest University for basketball. Meghan’s social status benefitted from her relationship with Steve her sorority, Kappa Kappa Gamma, was enthralled by him. The biography said “[Meghan’s] association with Lepore raised her stock with her Kappa Kappa Gamma sorority sisters, who were impressed that she had snared such a hottie.”

Shaun Zaken

Shaun wrote a royal story ( Image: Getty Images)

After Steve, she moved on to another Northwestern student, but this time they linked after they graduated. They dated for six moths, according to the Daily Mail and Shaun because a comedy writer. He doesn’t seem to be involved in Hollywood anymore. During his career, he co-wrote the show Two Princes which is suspiciously about royals. In the story, a modern day Prince lives in California which is very similar to Prince Harry’s life in Montecito.

Brett Ryland

Brett Ryland appears to have exited Hollywood ( Image: Getty Images for Invictus Games Dusseldorf 2023)

His book suspiciously has parallels to Harry ( Image: Getty Images for Invictus Games Dusseldorf 2023)
Meghan moved onto another Hollywood star, just not one quite as famous as the actress-turned-Duchess. She was linked with Brett Ryland after her college relationships. They were together for only five months. Thea actor, writer, and producer lives out in Los Angeles and was on shows like Mother’s Little Helpers and South of Nowhere. He also wrote for the show Two Broke Girls and some Disney Channel originals as well. He left entertainment to work as a business consultant.

Trevor Engelson

Trevor and Meghan are quiet about their divorce ( Image: Getty Images)
Not everyone knows that Meghan was married before Prince Harry. She met Trevor Enbelson in 2004 and dated for years before tying the knot in 2011. Their split was over “irreconcilable differences” and ruled a “no fault” divorce. Neither of the Hollywood stars have divulged details about what really went down beyond what the court documents showed which simply wasn’t much.

Cory Vitiello

Cory and Meghan don’t seem to have bad blood ( Image: Toronto Star via Getty Images)

Meghan then moved on to celebrity chef Cory Vitello, dating for two yeas. It wasn’t long after their break up that Meghan met Prince Harry and began her whirlwind romance with the royal.

Cory spoke with the Daily Mail about the relationship, explaining: “I’ve got a lot of respect for Meghan and, from my end, to make it seem like I’m part of the story would seem self-serving and opportunistic. I’m pleased for Meghan. She’s a great girl. There is no bitterness. I respect people’s private and personal lives, and although she has put herself in the public spectrum, I still hold to that.”

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Meghan Markle’s dating history includes a basketball player, chef, and a quiet divorce

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