On top of their surprising connection, Ish is also more than 20 years older than Madisson — which is bound to make some viewers question their relationship.
After facing the initial onslaught of judgment from friends and viewers alike, are Madisson and Ish still together?
Ish and Madisson of 'Siesta Key' fame survived the questioning and are still together today.
It looks as though the couple are still happily together, even after they faced flack. On Valentine's Day, Ish shared a photo with Madisson, captioning it, "My valentine now and forever!!"
Madisson has also continued to share shots of her and her sweetheart on her feed. On Jan. 14, after the season premiere, she shared a photo with Ish, updating everyone on their relationship. "Update: still happy #siestakey," she said.
She knows that not everyone is willing to accept her relationship — and sharing it with the Siesta Key viewers definitely adds extra judgment to their coupling.
"I get it. It's a big age difference but I would hope that after everyone initially judges it, will come around and see it's a real relationship with real feelings and he is good to me," she told E! News. "It's a healthy relationship."
To each their own, but if Madisson seems happy, it's really not our business to tell her otherwise.
What does her dad think of the relationship?
In the second episode of the season, we found out that Madisson's dad was less-than-pleased with her new man.
"Is he a father figure to you?" he asked on the show. "I think [the relationship] is a mistake, he's too old. This guy is going to be an old man when you're 39 years old. My hope would be that you would keep an open mind."
It was a hard conversation to have, and having it all filmed while it plays out doesn't make it any easier. But Madisson said that while the conversation was hard, she agreed to have it all play out on the show and share it with viewers.
"I have to give the show credit and production credit that it was all caught very organically on camera," she told Entertainment Tonight. "And I have to give Ish props for coming into this situation because he easily could have said no ... I have agreed to do this on camera and I have agreed to be truthful about my life and he wants to be with me and so he said, 'All right, if, whatever you want to do, I'm all in.'"
Fortunately, it seems like her dad is coming around to his daughter's new relationship, albeit slowly.
"He is coming around slowly but I think I need to give him more time than I was initially wanting to," she told the outlet. "Obviously, I want my dad to approve and want him to welcome my relationship with open arms and I didn't get that ... but I am learning that I need to also give him some space and time with that and I can't just expect him to come around right away."
But from the sounds of it, they're working on it, and hopefully her dad will see that she feels happy and healthy with Ish.
"You just get to see a whole deeper side to me. I feel like Ish brings out a really authentic part of me," she said. "I'm more open to love and have a stronger connection than I think I have ever had on television. I think all of my friendships have been real, but I think Ish brings out a whole different side of me."
Now they're in it for the long haul — Madisson and Ish are engaged!
In August 2020, Madisson took to Instagram to announce that Ish had asked her to marry him — and she said yes! "I have never felt as safe and as loved as I do when I'm with Ish," she told People. "He reminds me every single day how special I am and he makes me want to be the best possible version of myself. Our love story is anything but traditional, but it's OUR love story, and I can't wait to see how it plays out. I'm on such a high! I still can't believe it ... I've found my forever."
During the virtual Siesta Key reunion, Madisson shared the details behind the romantic proposal, which happened on the very first day that they spent together in their new home in Los Angeles. "So we bought our house, and then it was the first day that we spent in our house together," she said. "I was like, taking a selfie or something, and I turn around and he's on one knee. It was perfect."
There's no word yet on when they'll be tying the knot, but we'll definitely be staying tuned for more details. Congrats to the happy couple!