Since she joined The Real Housewives of New York City, we’ve seen Tinsley Mortimer date both a preppy boy toy and a bear-ish nerd.

Both cute, TBH. Both, however, are a stark contrast from the type of men Tinsley was linked to prior to RHONY. The mid-2000s darling of the New York tabloids has a torrid, strange, and very public record of dating rich, powerful, and occasionally famous men.

Let’s meet a few of her former suitors…

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Photo: Getty Images

Topper Mortimer
Age: 42
Gig: Finance guy, oil heir
Relationship: High school sweetheart

Tinsley and Topper’s love story reads like a pulpy teen romance from a bygone era. They met at at a tony prep school and fell so wildly in love that they ran off and got married in secret. The marriage, however, was short lived – his parents made them get an annulment when they found out.

Years later, when they got hitched again, they earned a coveted mention in the Style section of The New York Times. The Mortimer name, linked both to the Standard Oil fortune and to the very first Governor of New York colony, helped launch Tinsley on the New York social scene.

When Tinsley started doing the red carpet rounds, though, Topper was openly – and publicly – dismissive of her aspirations for fame, saying women who went to “good colleges” should have something better to do than be photographed at parties.

Tinsley started appearing alone more and more, both at charity functions and in the pages of Vogue, Vanity Fair and W. By 2009, there were reports of a split and allegations of cheating tossed at both parties.

The couple was, oddly, officially married for another four years, despite publicly date throughout their separation.

Which brings us to the Prince…

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Photo: The CW

Casimir Sayn-Wittgenstein-Sayn (a.k.a. Prince Casi)
Age: 41
Gig: German Royal
Relationship: Tinsley’s attempt at becoming Grace Kelly 

When Tinsley made her public debut with Prince Casimir, there were whispers the pair got together while Tins was still with Topper. Tinsley’s mother even told the press Topper asked Casimir to step aside so they could work on their marriage. Apparently he refused.

From what viewers saw on Tinsley’s short-lived reality show, High Society, the Prince was far from charming. He was openly hostile with Tinsley, yelling at her in public, and, according to her mom, was completely controlling her and even reading her emails.

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Photo: Getty Images

Constantine Maroulis
Age: 41
Gig: Broadway rocker, American Idol castoff
Relationship: Publicity-fuelled fling, high society detour

If Tinsley’s marriage to Topper was a teenage dream, her fling with six-place American Idol runner-up Constantine was more like a Glee arc. The most popular girl in school slums it with a theatre geek only to discover their worlds are too different.

At the time they dated, Constantine was on the up – his Broadshow show, Rock of Ages, was a smash success and he’d just been nominated for a Tony. Still, it was a minor scandal in New York when the Park Avenue Princess jumped from her high society husband to a literal Prince to… that curly haired guy from American Idol.

By most accounts, the relationship was simply fodder for Tinsley’s show, on which Constantine eventually appeared, but they continued to appear at events together for several months after filming.

On camera, Constantine was good to Tinsley, but just three months after they split, news broke he was having a child with one of the chorus members from his show. That relationship eventually turned sour: In 2015, the woman, Angel, alleged that he viciously assaulted her. The next year, a pickup at their daughter’s school turned physical, leading to Angel’s arrest.

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Photo: Getty Images

Lorenzo Borghese
Age: 45
Gig: Businessman, former Bachelor
Relationship: Photo fling

In 2010, Tinsley was briefly romantically linked to Bachelor star Lorenzo Borghese. The news was yet another romantic scandal, since Lorenzo had previously dated Tinsley’s sister Dabney. It turned out the sisters don’t really share everything, though –  it seems like these were simply pals who posed for a few photos together. (No word on whether the same is true for Sonja Morgan, who was also captured in photos looking cozy with Lorenzo.)

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Photo: Getty Images

Brian Mazza
Age: 32
Gig: Nightclub owner, party promoter
Relationship: Tinsley’s first taste of arm candy

Brian was Tinsley’s first younger boyfriend. They dated for just over a year without any real scandals. Mostly, they seemed to spend a lot of time on the beach, looking hot together.

Alexander “Nico” Fanjul
Age: 31
Gig: Billionaire sugar heir
Relationship: Toxic

After leaving New York for Palm Beach, Tinsley got together with a rich kid 10 years her junior. As Tinsley’s discussed on RHONY, the relationship eventually led to her arrest for trespassing on Nico’s property. But even before that, there were very serious problems, including serious allegations of abuse.

Over the span of their four-year relationship, the couple was the subject of four police reports and a written warning from the cops. After one incident, Tinsley reportedly had to get three staples in the back of her head. She also claimed he tried to smother her with a pillow.