Joshua Goldman
Joshua Goldman
min read · September 28, 2025 · Entertainment

Meghan Markle's Love Life Before Harry: From Starry Ambitions to Royal Romance

Meghan Markle is pictured with her father, Thomas Markle, at her college graduation

Meghan's Rise to Royalty: A Star is Born

In the City of Angels, Meghan Markle grew up with a burning desire to shine bright on stage and screen. As a young girl from Los Angeles, she was no stranger to the world of entertainment. Her father, Thomas Markle, a successful TV lighting director, spared no expense in giving his daughter the best of everything. He even took her as his plus one to the Emmy Awards when he was nominated.

But Meghan's privileged upbringing and connections didn't shield her from making mistakes. Insiders claim that she had her pick of college basketball heartthrobs, and her father revealed that she once pointed out a guy in class and declared, "That boy is going to be my boyfriend!" And guess what? She got her man!

Tina Brown wrote in her book, The Palace Papers: 'At college, she had her pick of the sought-after basketball hunks'

Meghan's first serious relationship was with Steve Lepore, a college basketball star from Northwestern University. The couple dated for five months before calling it quits when Steve accepted an offer to attend college in North Carolina. But sources close to the couple described them as "quite the pair" and Meghan's ambition and drive were already making waves.

The duchess-to-be later dated fellow actor Shaun Zaken, whom she met while studying at Northwestern. Their six-month romance in 2003 was just one of several high-profile relationships that would make headlines years later. She also dated Brett Ryland for five months before meeting Trevor Engelson, a successful American film producer.

Meghan and Trevor's whirlwind romance began when they met in a bar when both were just 23. Sources claim that Meghan was immediately drawn to Trevor's "tender dynamic" but was frustrated by his lack of ambition on her behalf. The couple got married in 2011, with Trevor's friends and family questioning Meghan's sudden request for no social media at the wedding.

Before meeting Harry, Meghan was dating American film producer Trevor Engelson. The two reportedly met in a bar when they were 23, with Brown describing them as having a 'tender dynamic'

But it seemed Meghan had bigger aspirations than being a Hollywood wife. She left Trevor after two years of marriage, citing "irreconcilable differences" and eventually divorcing him in 2013.

The duchess's last relationship before meeting Prince Harry was with Canadian chef Cory Vitiello, whom she dated for two years until their breakup in 2016. But when it comes to her romance with the Prince of Wales, Meghan's claims about being a "blank slate" and doing no research on Harry have been met with skepticism.

Insiders claim that both Meghan and Harry did their homework before meeting at Dean Street Townhouse in 2016. They even Googled each other! Tom Fitzgerald, a commentator for Vanity Fair, stated, "Meghan is the type of woman who would check a menu out online before going to a restaurant... so the idea that she didn't know she was supposed to curtsy for the Queen just doesn't ring true."

Biographers Carolyn Durand and Omid Scobie stated in their book, Finding Freedom, that Meghan and Harry would have both done 'their homework' on one another before meeting

But what's truly astonishing about Meghan's rise to royalty is how quickly she adapted to her new role. Sources close to the couple claim that she was fascinated by the Royal Family even as a child, and had Diana: Her True Story on her bookshelf. In fact, Meghan once wrote about having childhood fantasies of being a princess!

Fast-forward to 2023, and Meghan has become a global superstar with her own Netflix series, lifestyle brand, and podcasts. She's successfully navigated the world of royal protocol while also maintaining her Hollywood edge.

As she settles into her grand Montecito mansion with Prince Harry by her side, it seems like Meghan Markle is living her ultimate fairy tale. And judging from her dazzling public image and enviable lifestyle, who can blame her?

References:

  • TheScholarlyNote.com
  • Carolyn Durand and Omid Scobie's book Finding Freedom
  • Tom Fitzgerald's comments for Vanity Fair
  • Ninaki's interview with thescholarlynote.com in 2018