Love Bites! Celebrities With Major Relationship Regrets: Taylor Swift, Kim Kardashian and More

Taylor Swift

In Taylor’s song “Invisible String” off her eighth studio album, Folklore, she sings, “Cold was the steel of my axe to grind/ For the boys who broke my heart/ Now I send their babies presents,” and many fans believe she’s referencing Joe. 

Nikki Bella

“I have many regrets about that relationship. The primary one is that I wish I’d known myself better before I got into it,” the Total Bellas author penned in her 2020 memoir, Incomparable, referring to ex-fiancé John Cena. 

“I wish I’d understood how the patterns in my life, and my relationship with my own father, informed how I react to love, boundaries and feelings of abandonment. I think I could have averted some of what happened,” Nikki added. “Because my dad left when I was 15, I learned how to fill in the holes. I expect to be left behind and to find a way to not confront or acknowledge those feelings of loneliness and abandonment.”

Nicole Kidman

During a 2016 interview with Red, the Big Little Lies actress reflected on her marriage to Tom Cruise. “I look back now and I’m like, ‘What?’ You look at Taylor Swift, I mean how old is she? She’s 26,” Nicole expressed. “I had two kids by the time I was 27 and I’d been married for four years. But that’s what I wanted.”

Kris Jenner

“The one regret, if I had to do it over, would be divorcing Robert Kardashian … But then there wouldn’t have been Kendall and Kylie, so that’s the way I look at it,” the former Keeping Up With the Kardashians star previously told New You, referring to daughters Kylie Jenner and Kendall Jenner, whom she shares with ex Caitlyn Jenner. “Everything happens for a reason, and we learn from our mistakes. I thought I was so smart when I was young; I was fearless.”

Kim Kardashian

Although the KKW Beauty mogul is in the process of divorcing estranged husband, she once said she wished she settled down with him sooner.

“There’s just something [now] where I feel I’m so equal with my husband, like, ‘This is my best friend.’ And I think it helps that we were friends for so long and knew each other for almost 10 years. There was flirting before, so it was obvious there was attraction, but there was a moment in my mind that clicked when I was like, ‘I’m going to give this a shot.’ I was probably so tired of bulls–t in the past. I’d gone through a divorce six months before. And I was like, ‘This guy has never bulls–tted me. He had made it clear that this is what he wants, why don’t I give it a shot?’ I went through so many mistakes that must have hurt Kanye, watching me get married, knowing, that’s not the right situation for you,” Kim recalled to Glamour in 2015.

“So, it was a great feeling when I was finally like, ‘OK, this is it.’ My only regret is that I didn’t give it a shot sooner,” she added. “It would have saved so much BS. I feel like I got the fairytale. I should have had even higher expectations, because I got the fairytale.”

Gwyneth Paltrow

The Goop founder doesn’t have a specific relationship regret, per se. “I’ve f–ked up so many relationships, so many. I’m actually a pretty good friend, and a good sister and a daughter and a mother, but I’m at my potentially most vulnerable and f—ked up in the romantic slice of the pie,” Gwyneth revealing during a 2017 episode of the “Girl Boss” podcast. “So, it’s taken me a lot of, a lot of work to get to the place where I have a good romantic relationship.”

Calvin Harris

The Scottish DJ opened up about his breakup from Taylor Swift in 2016 interview with British GQ.

“The aftermath of the relationship was way more heavily publicized than the relationship itself. When we were together, we were very careful for it not to be a media circus. She respected my feelings in that sense. I’m not good at being a celebrity … but when it ended, all hell broke loose,” Calvin recalled. “Now, I see that Twitter thing as a result of me succumbing to pressure. It took me a minute to realize that none of that matters. I’m a positive guy. For both of us it was the wrong situation. It clearly wasn’t right, so it ended.”

Madonna

Madonna first married Sean Penn in 1985, and the two called it quits just four years later in 1989. She then went on to marry director and actor Guy Richie in 2000, but that relationship also ended in divorce.

Promoting her ​2022 album, Finally Enough Love, the singer allowed people to ask her questions on her YouTube Channel. One fan asked if she had any regrets in her life.

“Getting married. Both times,” Madonna quipped.

Kristen Stewart

Kristen Stewart and Robert Pattinson first met during their audition for the film Twilight, and it didn’t take long before the two developed a connection. However, it wasn’t until almost three years later in 2010 that their relationship was officially confirmed.

On July 24, 2012, while filming the movie Snow White and the Huntsman, Kristen was photographed kissing the director of the film, Rupert Sanders.

The next day, the MK Ultra star issued an apology to Robert.

“I’m deeply sorry for the hurt and embarrassment I’ve caused to those close to me and everyone this has affected. This momentary indiscretion has jeopardized the most important thing in my life, the person I love and respect the most, Rob. I love him, I love him, I’m so sorry,” Kristen said in the statement.

In May 2013, the couple split for good.

Jude Law

Jude Law met Sienna Miller when they both filmed the 2004 film, Alfie. In December of that same year, Jude proposed to Sienna, but they never made it down the aisle. In May 2005, Jude was revealed to be having an affair with his children’s nanny, a decision he ultimately regretted.

“Following the reports in today’s papers, I just want to say I am deeply ashamed and upset that I’ve hurt Sienna and the people most close to us,” Jude told the British Press Association. “I want to publicly apologize to Sienna and our respective families for the pain that I have caused. There is no defense for my actions which I sincerely regret and I ask that you respect our privacy at this very difficult time.”

Melissa Joan Hart

Melissa Joan Hart popped up on the Hollywood scene with her hit ​’90s Nickelodeon show, Clarissa Explains It All. She later went on to become the titular star in the series Sabrina the Teenage Witch, which spurred a 1996 TV movie of the same name.

Ryan Reynolds was cast as the object of Sabrina’s affection in the film, and Melissa admitted that she regrets not going on a date with the Deadpool star.

“I had a boyfriend at the time,” Melissa told Australia’s Studio 10 talk show. “Ryan probably would have been a great boyfriend. And I didn’t end up with the other guy, so maybe I should have taken a chance!”