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All the men Paris Hilton almost walked down the aisle with

Congratulations Paris and Carter!


Jovita Trujillo
Jovita Trujillo - Los Angeles
Senior WriterLos Angeles
NOVEMBER 12, 2021 7:19 PM EST

America’s royal wedding is all the world can talk about as Paris Hilton tied the knot with Carter Reum on Friday. While it is Paris’s first wedding, it’s not the first time she has had a diamond ring on her left hand. The heiress has been engaged 3 times in her 40 years on earth with short-lived hopes of forever. Her story is testimony that just because the diamond is huge it’s going to work out because Reum’s ring was actually one of the more humble diamonds she has received, estimated at $1 million. Take a look back at the men who thought they would be the ones walking the DJ down the aisle:

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JASON SHAW (2002)

Hilton first said yes when she was 20 to model Jason Shaw who was 8 years older than her. Their engagement only lasted a few months and they called it off in 2003. He proposed with a large pear-shaped diamond set on a gold band.

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PARIS LATSIS (2005)

After calling off her first engagement it only took 3 years before the reality star said yes for the second time. In May 2005 she got engaged to Paris Latsis. They only dated for 8 months before Latsis knew he wanted to marry Hilton. The Greek shipping heir brought Hilton 15 different engagement rings from high-end jewelers for her to choose from, per E! Online. She reportedly chose a 24-carat $5 million ring which is her most expensive by far, per Brides. Just a few months later in September Hilton revealed, “I‘m sad to announce that I’ve called off my engagement. Over the last couple months, I‘ve realized that this is the right decision for me. We remain best of friends, and I’ll always love him. I hope people will respect my privacy during this emotional time.”

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CHRIS ZYLKA (2018)

The third time isn’t always a charm. Hilton announced her engagement to actor Chris Zylka who proposed with a gorgeous 20-carat ring It featured a pear-cut center stone surrounded by a halo of diamonds and set on a double diamond pavé band, per Brides. It was one of her longest engagements, lasting 10 months before they split in November of that year. At the time, Paris talked to Entertainment Tonight and revealed her maid of honor would be her sister Nicky Hilton. “It’s just obvious,” she said. “She’s my best friend and she’s, like, my other half. I love her so much. So, of course, she’s going to be my maid of honor.” While Paris never walked down the aisle with Zylka, Nicky was her maid of honor today.