The Challenge: Tony Raines and Alyssa Giacone announce wedding date after five-year engagement

tony raines in the challenge final reckoning on mtv
Tony Raines during his Final Reckoning season of The Challenge. Pic credit: @TheChallenge/YouTube

Former The Challenge finalist and Real World: Skeletons star Tony Raines is “finally” getting married after an engagement that lasted five years.

The 34-year-old shared the big news this past week that he’s set a wedding date with fiancee Alyssa Giacone, whom he met before his reality TV days and continued dating off-and-on during his time on MTV.

Based on Tony’s Instagram share, they’ll “officially be Mr. & Mrs. Raines” on Saturday, October 14.

Along with his announcement, Tony shared a heartfelt video slideshow featuring engagement photos set to Morgan Wallen’s song Cover Me Up.

In several photos, Tony wears a crisp light-blue button-up shirt and blue jeans, while Alyssa wears a stunning pink shoulder-less dress. 

In other images, Tony has on a white button-up along with grey slacks, while Alyssa wears a beautiful white dress with a floral pattern and sheer look to part of it.

They’re shown walking together and embracing in the woods, the water, or on the beach. One shot shows the couple holding hands with an engagement ring visible.

“Big thank you to our photographer @tiffinihelg ? Our engagement pics couldn’t have turned out better!” he wrote in the caption, including hashtags such as #BlessTheRaines, #LetsGetMarried, #Love, and #TieTheKnot.

According to E! Online, Alyssa and Tony have one daughter together, Isla Rose, and also share Tony’s daughter Harper London, whom he had with his ex Madison Walls.

Castmates and Challenge alum react to Tony’s announcement

Tony’s big announcement on Instagram caught the attention of many fans and friends, including some of the stars of The Challenge. Among those dropping by to offer congratulatory comments or jokes were Kyle Christie, Mark Long, and Jemmye Carroll.

“Congratulations I can’t wait to be the best man!” Kyle joked with his Challenge castmate.

Michaela and Mark each offered congratulations, while Jemmye wrote, “My heart is so full for y’all.”

stars of the challenge comment on tony and alyssa news
The Challenge stars congratulate Tony and Alyssa. Pic credit: @t_raines/Instagram

Tony’s friend Derrick Kosinski gave an ecstatic “Wooo hooooo!!!” while Ruthie Alcaide left four heart emojis to show the love for the couple’s announcement.

As of this writing, Tony’s IG announcement post with its sweet slideshow video had over 20,000 likes and 220-plus comments, as many others expressed congratulations and good wishes to the couple.

Tony’s news arrived around the same time as other big news from The Challenge. Multi-time champion Wes Bergman shared Baby Bergmann is on the way, as his wife Amanda is carrying their first child.

Tony proposed to Alyssa at The Challenge reunion special five years ago

Tony began dating Alyssa before he ever appeared on any MTV reality TV programs. However, their situation changed before his debut on Real World: Skeletons, which also featured future Challenge alum Nicole Zanatta and Sylvia Elsrode as castmates.

Alyssa was Tony’s ex then and showed up as one of the “skeletons” from his past for the unique Real World theme. At the time, Tony had been attempting to get with his RW castmate, Madison.

Tony continued to appear on reality TV with MTV’s The Challenge, with his relationships with Madison or Alyssa often part of his spotlighted story during the seasons.

Ultimately, he proposed to Alyssa during The Challenge: Final Reckoning reunion special five years ago. During part of the event, he got down on one knee and popped the question with castmates there to cheer him on and offer congratulations after she said “yes.”

Monsters and Critics previously reported about Tony and his family’s rough time during Hurricane Ida. The storm caused damage to their home and resulted in Alyssa suffering some tough injuries requiring medical treatment, including surgery.

They’ve been through thick and thin for over five years, but their relationship has endured. They’ll officially become husband and wife in October, with friends and family, likely including some Challenge castmates, at their wedding ceremony.

The Challenge: World Championship episodes arrive Wednesdays on Paramount Plus.

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