‘The Challenge’ Star Tony Raines Is Engaged: ‘Real World’ Alum Proposes To His ‘Skeleton’ Alyssa

Alyssa Giacone went from ‘skeleton’ to fiancé! ‘The Challenge’ star Tony Raines announced his engagement to his baby mama on Oct. 13, and here’s how they feel about it.

High school sweethearts Tony Raines and Alyssa Giacone will soon share Mr. and Mrs. titles! The Challenge star announced the happy news with a PDA picture on Oct. 13. His fiancé, whom he shares one-year-old Isla Rose with, had no clue he was going to pop the question. “Oh my god, I had no idea,” Alyssa admitted to MTV News. “I’m over the moon, and I can’t wait for him to be my husband.” And the future groom revealed how long he’s been planning to get down on one knee!

“I’ve been thinking about this [proposal] since Dirty 30,” Tony revealed to MTV News, referring to Season 30 of The Challenge. “I had a conversation with CT [Tamburello] while filming Dirty 30 about him marrying Lili [Solares] and me marrying Alyssa.” Tony’s referring to his castmate, CT, who just got married on Sept. 9! “When we won Champs vs. Stars together, he gave me the trip as an engagement or honeymoon gift. Alyssa and I were invited to his wedding and had a blast there. You’ve all seen me grow so much over the seasons. Now, proposing here to Alyssa and getting engaged feels like the perfect ending to the Trilogy.” HollywoodLife even had an EXCLUSIVE chat with Tony after he won the show with CT!

Tony and Alyssa were going eight year strong before she became one of Tony’s “skeletons” on The Real World: Skeletons, which aired from 2014 to 2015. They had another hiccup when Tony was caught cheating with The Challenge co-star Camila Nakagawa on the Dirty 30, aired for all to see. Yes, awkward, considering that’s when he started to consider marriage with Alyssa! He tweeted an apology letter in September of 2017. “I’m beyond upset at myself and regardless of how it comes across on air I blame no one but myself,” part of the statement read. “Maybe I’ve apologized too many times or not enough about all the mistakes I’ve made but I am very aware of my issues and everyday I’m growing and maturing.”

We’re just thrilled Tony and Alyssa were able to reconcile their relationship! Tony shares one other child with former Real World co-star Madison Channing Walls.

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