"I Don't Regret Anything": The Craziest Video Messages in Temptation Island History

One of the highlights of Temptation Island is the video messages that the couples send to each other from their respective villa. As we’ve already seen in past seasons leading up to Season 5, things can take a sharp turn and cause even more drama after couples are permitted to "speak" to one another again — albeit briefly and not in person. Viewers know there's a catch when it comes to couples sending videos: They don’t have to send one to their significant other if they don’t want to, which often results in hurt feelings and more confusion than before.

Season 5 introduced a new element to the videos in previous weeks by allowing the singles to send video messages to anyone in the other villa, and it’s already been awkward, explosive, and tugged at the emotional heartstrings.

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Hall’s message to Kaitlin was not what anyone was expecting from him. It was dry and void of emotion as he told her he admired her strength and beauty, but that he had also found true happiness in himself. Single Makayla also sent a message to Kaitlin to thank her for bringing Hall to the island. And on the opposite end of the spectrum, Kaitlin’s message to Hall was full of love and hope as she expressed she was hurt by his questioning of their relationship. Hall, stunned, immediately demanded to see Kaitlin, leaving viewers with a cliffhanger for the Temptation Island record book ...

So, in honor of Hall and Kaitlin's potentially explosive back-and-forth, here’s a look back at some of the craziest video messages in Temptation Island history. 

Season 1: Evan Ignores Kaci

In Season 1 of Temptation Island, there was one video message that was loud and clear. Evan didn’t send his girlfriend Kaci a message at all. The hurt she felt over the silence was intense. Meanwhile, she sent him a tearful video message saying she wanted him to be the man she knows he can be and not to give up on her or their relationship. Evan broke down in tears and said she doesn’t deserve this, and he said he could see “that poor girl” is hurting so bad. Ultimately, they went their separate ways by the end of the season. 

Season 2: Casey's Fake Ugly Cry

In season 2, Casey attempted an ugly cry during his video for Ashley H., but the tears were missing. He told her he wanted to marry her and have a family and declared how much he loved her.

Ashley wasn’t here for his dramatics. She had been waiting for Casey to say those things, but it took him bringing her to Temptation Island to do it. That just wasn't good enough. In her video message back to him, she thanked him for bringing her to the island because she gained her confidence and shed any jealousy and insecurity. “I don’t regret anything,” was the final blow heard around the world. He was shook, and cried into his hands while saying, “she didn’t say 'I love you.'"

Season 3: Kendal's Excuses

There was already drama surrounding Kendal, Nickole, and Alexcys and the threesome that shocked everyone in Season 3. Kendal's girlfriend Erica was hoping he didn’t send her a message but unfortunately for her, he was full of excuses and saying he was fully embracing the experience on the island to cover for his actions. Of course, he flipped it back on her by saying he hoped she would turn into the woman he knew she could be, and they would leave stronger together. Erica was shocked that he believed they would leave together, so to drive that notion into the ground, she didn’t bother sending him a video.

Season 4: Ashley Outgrows Lascelles

Temptation Island Season 4 featured one jaw-dropping video message that caused a ripple of applause across the internet after it aired. Ashley Rodriguez sent her then-boyfriend, Lascelles Lagares, a passive-aggressive video message stating that she deserved better than what she was given in their relationship. She also said that she was not hiding the truth anymore and was happy with the woman she was becoming day by day. She demanded respect as she shared her feelings, which made fans happy. Meanwhile, Lascelles sent her a message declaring his love for her — but Ashley didn’t believe him. 

Temptation Island airs Wednesdays at 9/8c on USA Network. Catch up on past episodes on Peacock now.