When someone heads to prison, you never expect them to find romance, but Gypsy Rose Blanchard made it happen. A family friend, Fancy Marcelli, revealed to InTouch Weekly that Blanchard had developed relationships with multiple men during her ten-year prison run. She shared, “These are guys from the support groups, the Gypsy support groups. They attached themselves to Gypsy, and a lot of them just want fame … Some of the guys have even gone to the prison to meet Gypsy.”

One of these men who attempted to get to know Gypsy was “The Bachelorette” alumni Josh Seiter. According to InTouch Weekly, Seiter sent Gypsy a flirty email in prison, but she was in a relationship and didn’t find the reality star’s pursuit of her genuine. She reportedly wrote back, “I don’t know who you are, or why you chose ME to try and find your 15 minutes of fame, but I have friends everywhere and I know what lies you’ve told online.” While she wasn’t interested in Seiter, Gypsy did eventually develop a strong connection that turned pretty serious.

According to E! News, in 2019, Gypsy accepted a proposal from a longtime pen pal, Ken. Ken would visit Gypsy in prison and even met her father and stepmother. Although Gypsy may have thought she found her happily ever after, her engagement didn’t last long. Her stepmother confirmed to InTouch Weekly that she called it quits with Ken months after he popped the question.

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