Kenny Chesney is one of the most successful country singers on earth; there’s no doubt about that. But he hasn’t been very successful in love as he has been in music. He went to a divorce that led to nasty rumors. He had a series of failed relationships and, finally, one that is going steady today. Is it going to be forever with Kenny Chesney?

Let’s take a look back at the “When The Sun Goes Down” singer’s intriguing dating life.

His Ex-Wife Divorced Him After Four Months Of Being Married

Kenny Chesney and Renée Zellweger took the world by surprise when they got hitched in May 2005 after knowing each other for only five months. But the bigger surprise came when the two decided to have their marriage annulled just four months later — with the actress citing “fraud” as the reason.

In 2010, Kenny went on Oprah, and he has addressed their short-lived relationship. When Oprah Winfrey asked the “There Goes My Life” singer if the lack of time contributed to their annulment, Kenny responded, “that and the fact that I panicked.”

“I panicked, there’s no doubt about it,” he said about his reaction to the overwhelming media attention that came with his marriage. “I did the only thing I knew to do — I ran. I pushed her away … I didn’t have any clue as to what true marriage meant. I was so used to committing to one thing — music –and then I had to totally commit to a second thing, marriage. I didn’t know how to commit to both of them.”

Is Kenny Chesney Gay? We Don’t Think So

Kenny Chesney’s divorce has led to one big question, is he gay? Well, the answer is that he is straight as an arrow. You can ask the more than 100 women he’s bedded!

The rumors started after the wording on the Reneé Zellweger’s annulment papers, which cited “fraud” as a reason for their split. Later on, Kenny explained that Renée checked the “fraud” box on the annulment documents because they believed it was the “least harmful.” 

“The only fraud that was committed was me thinking that I knew what it was going to be like, that I really understood what it was like to be married, and I really didn’t.”

In 2016, Renée also clarified while speaking with The Advocate that the term “fraud” was “simply a legal term and is not a reflection of Kenny’s character.” She also said that the rumors about Kenny made her sad.

“It made me sad that somehow people were using that as a way to be cruel and calling someone gay as a pejorative, which has fateful consequences. Of course, there’s the bigger-picture problem of why anyone had to make up a story at all.”

The country superstar has also opened up about the gay rumors.

“What guy who loves girls wouldn’t be angry about that? I didn’t sign up for that,” Chesney told Playboy magazine of his reaction to the rumors. “I’m pretty confident in the fact that I love girls [laughs]. I’ve got a long line of girls who could testify that I’m not gay.”

There’s indeed a long line.

“There were years when I had a better summer than A-Rod,” Chesney boasted, adding that he’s been with “over 100” women. “My first five years on the road were intense because I was the guy in college who never got laid until I started playing guitar.”

Series of Failed Relationships

After going through a divorce, Kenny Chesney was not in the best shape. Luckily, he met Amy Colley, a burn-unit nurse, and was also Miss Tennessee 2005. Amy was the next lucky girl to call Chesney her boyfriend, and she absolutely revived his spirits.  

The two were often spotted several times happily vacationing on the clear beaches of the Malibu and Bahamas. The relationship eventually became serious that they even took each other to Thanksgiving vacations with one another’s families.

However, Kenny and Amy’s relationship started to fall apart slowly. The final straw was when Chesney had been spotted hanging out with another woman in Cancun, Jenn Brown. Brown started as a Division One college athlete and eventually made it to becoming a successful ESPN broadcaster. She has been on the sidelines of several massive college football games as well. She once made history when she became the first female correspondent of Inside The NFL. Amy, on the other hand, after being Kenny’s devoted lover for two years, was devastated to found out about Kenny Chesney’s affair with Jenn. 

Rumors also spread once that Chesney was dating Miranda Lambert, but it turned out to be a folk tale.

He Found A New Love

At present, Kenny Chesney is happily in a relationship with his girlfriend, Mary Nolan, who he has been together with since 2012. Nolan has been seen beside Chesney in a couple of awards shows they attended together, such as the CMA Awards and the Country Countdown Awards. 

She was also seen kissing Kenny Chesney on the cheeks after the country singer has received the Pinnacle Award. Things seem to be going steady and serious for the couple as rumors also abound of engagement between the two happening soon. Guess we’ll have to wait and see.