Johnny DePhillipo Opens Up About His Direct Message to Jennifer Aniston and Exposes His Admiration for the 'Golden Bachelor'

Following his tumultuous breakup with former fiancee Victoria Fuller, Johnny DePhillipo has been relishing his single status. The Bachelor Nation ​star took a daring step by messaging Jennifer Aniston in an attempt to woo her, and also confessed his interest in April Kirkwood from The Golden Bachelor.

"I must admit, I did send a Direct Message to Jennifer Aniston. I couldn't resist, she's my dream woman," the 27-year-old Johnny confessed to Page Six during a game of truth or dare, over drinks published on Tuesday, December 19. "I think I told her something like, ‘You are beautiful.’ I'm not clear."

The Bachelor in Paradise alum checked his phone only to find that the Friends star, aged 54, had not responded, and he had withdrawn his message. He then sent her another Direct Message expressing for the second time how "beautiful" she is.

After a few shots of tequila, Johnny revealed his wish to date someone from the Bachelor Nation, and surprisingly, it wasn't Hunter Haag, with whom he had been exchanging messages for quite some time.

"The new season's April is kind of attractive," he admitted, before adding that he needs an older woman or "cougar" in his life and toasting to her.

"April, you've experienced the old, now it's time for the young," he suggested, referencing Gerry Turner from The Golden Bachelor. "Take a leap of faith. April, you're beautiful.”

Fans were first introduced to Johnny during Gabby Windey and Rachel Recchia's duo season of The Bachelorette. After Gabby, 32, rejected him, he joined the season 8 cast of Bachelor in Paradise and fell into a whirlwind relationship with Victoria, 30, after pairing up at the second rose ceremony of the season.

The couple maintained their engagement post filming with Bachelor Nation fans catching a glimpse of Johnny in an Instagram video by Victoria in August 2022. Two months later, Zachary Reality revealed that a BiP engaged couple had "already separated", and everything indicated Johnny and Victoria.

Subsequently, former medical sales rep found herself amidst cheating rumors with her current boyfriend Greg Grippo after fans noticed them together in Italy. Victoria negated the allegations on Johnny, but confirmed her association with Greg, 27, in November 2022 during BiP season 8 reunion.

During the reunion, Johnny and Victoria addressed their split, but had different takes on it. The influencer stated she would have dissolved the engagement had their arguments been "this incessant, this early and this toxic." Contrarily, Johnny stated termed Victoria’s involvement with Greg as “switching sides” and blatant emotional cheating.

"Interacting with someone else while we are trying to resolve our issues, be it emotional, I still see it as cheating," Johnny told Victoria. "I wish you the best in life and I think it's time for me to take a step back and restructure myself.”