When you have a season of The Challenge as dramatic as Final Reckoning was, you know the reunion is going to be, as the kids say, fire. The promos for the two-part reunion special promise all kinds of confrontations that fans have been waiting for all season, but also what looks like a proposal. So does someone get engaged during The Challenge: Final Reckoning reunion? It would be a small ray of sunshine in an otherwise winner-take-all kind of season. In one of the promos for the reunion, Tony Raines gets down on one knee in front of his high school sweetheart Alyssa Giacone, who he also shares a two-year-old daughter with. And while the preview doesn't show what he says or if it is indeed a marriage proposal, according to Tony’s Instagram, he and Alyssa are engaged and loving it.
In October, around the same tie the reunion was likely filmed, Tony posted a photo of himself with Alyssa sporting a pear-shaped solitaire and the caption, "We’re engaged!" and tagged Times Square, where the reunion was more than likely filmed. In another photo of the newly engaged couple, Alyssa is wearing the same green jumpsuit she’s seen wearing at the reunion, so it's definitely possible that the they got engaged at The Challenge: Final Reckoning reunion taping.
Tony’s first taste of MTV came back in 2014 when he appeared in Real World: Skeletons and hooked up with fellow cast member Madison Channing Walls before his skeletons arrived in the form of two ex-girlfriends, including Alyssa. Although they’d been broken up at the time, it was still tough for him to have Alyssa and his other ex in the house while he was falling for Madison. He still managed to have a relationship with Madison outside of the house and they now have a two-year-old daughter, but shortly after, he rekindled things with Alyssa.
Things weren't always so smooth for the couple. During his time on The Challenge: XXX which aired in 2017, he was caught cheating with a co-star. At the time, he called Alyssa to deny what had happened on-camera, but later tweeted a public apology to his now-fiancée. "I'm beyond upset at myself and regardless of how it comes across on air I blame no one but myself," he wrote. "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 up and maturing."
Despite the ups and downs of their relationship that unfortunately played out on social media and on TV more often than not, it looks like Alyssa and Tony are doing better than ever and seem to have a healthy relationship with Madison. Alyssa and Tony regularly post photos with both of Tony’s daughters and they seem to be one happy blended family. So while this season of The Challenge may have been full of some serious animosity among competitors, Tony’s proposal at the reunion was one of the good things to come from it.
While the couple hasn't yet set a date, they could potentially follow in the footsteps of fellow Challenge star C.T. Tamburello, whose wedding special, The Challenge: CT’s Getting Married, will air on MTV on Dec. 11. Real World and The Challenge fans alike might remember CT from his years in and out of the separate franchises and if he can get his own TV special, then maybe Tony and Alyssa will get the same star treatment. Right now, however, it looks like they’re just enjoying being engaged.
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