Kellie’s songwriter boyfriend, Kyle Jacobs, proposed to her on a beach at sunset after dated for over two years. She said yes. Kellie and Kyle got married in a surprise wedding on New Year's Day 2011 in the Caribbean.
After two and a half years of dating, Pickler became engaged to songwriter Kyle Jacobs on June 15, 2010, the day of her late grandmother's birthday, after he proposed on a beach at sunset. Pickler related for a background piece on Dancing with the Stars that the couple had planned an elaborate ceremony, but as the date approached, "I looked at him and said, 'Baby, this ain't us.'" On January 1, 2011, she and Jacobs eloped and married in a "small, intimate ceremony on a private island in the Caribbean".