Who is Kenny Chesney Dating Now? A Look at His Past and Present Relationships


Kenny Chesney is a renowned American country music singer and songwriter, known for hits such as “No Shoes, No Shirt, No Problems” and “She’s Got It All.” Over the years, he has been linked to several women, and his dating life has been the subject of many tabloid rumors. In this article, we’ll take a closer look at Kenny Chesney’s past and present relationships, as well as any rumors and facts surrounding his dating life.


Relationship Wiki Table:

Name Relationship Type Dates
Renee Zellweger Marriage May 2005 – Dec 2005
Amy Colley Relationship 2008 – 2010
Jamie Hill Relationship 2008
Jenn Brown Relationship 2011
Mary Nolan Relationship 2012
Adrianna Costa Rumor 2013
Vanessa Millon Relationship 2013 – 2015
Jamie Hill Fuller Rumor 2016
Caroline Jones Rumor 2018 – 2019
Mary Poppins Fictional Rumor N/A


Past Relationships:

Kenny Chesney was famously married to actress Renee Zellweger for just four months in 2005. The couple met in January of that year, and Chesney proposed to Zellweger in April. They tied the knot on May 9, 2005, in a private ceremony in the Virgin Islands. However, in September of that year, they announced their separation, with Zellweger citing “fraud” as the reason for their split. The annulment was finalized in December of that year.

Following his marriage to Zellweger, Chesney dated several women, including Amy Colley, Jamie Hill, Jenn Brown, and Mary Nolan


Current Relationship Status:

Kenny Chesney’s current relationship status is unknown, as he has not publicly confirmed any relationships since his breakup with Vanessa Millon in 2015.



Over the years, there have been several rumors about Kenny Chesney’s dating life. In 2013, it was rumored that he was dating TV personality Adrianna Costa, but the rumors were never confirmed. In 2016, there were rumors that he was dating his ex-girlfriend Jamie Hill Fuller, but again, there was no confirmation.

In 2018 and 2019, there were rumors that Chesney was dating singer-songwriter Caroline Jones, who had previously opened for him on tour. However, the rumors were never confirmed, and both Chesney and Jones remained tight-lipped about their alleged relationship.



Kenny Chesney’s most recent confirmed relationship was with Mary Nolan, whom he dated in 2012. However, the couple reportedly split later that year.



  • Kenny Chesney was born on March 26, 1968, in Knoxville, Tennessee.
  • He has won several awards throughout his career, including four CMA Awards and six ACM Awards.
  • Chesney has sold over 30 million albums worldwide, making him one of the best-selling music artists of all time.
  • He is known for his philanthropy, particularly his work to help the victims of Hurricane Irma in 2017.
  • Despite rumors to the contrary, Chesney has never been romantically linked to the fictional character Mary Poppins.