The first thing that attracted The Pioneer Woman to this cowboy was his salt and pepper hair on his young face, but she recalls in a 2017 essay that it was his hands that sealed the deal, “They were big and strong,". Drummond calls her husband "The Marlboro Man" because of his masculine, country appearance.

They hit it off the night they met, talking into the night, to the bemusement of her friends. Ree didn’t know Ladd’s name when they first met, and weeks went by with no word from the handsome stranger. After four months she decided to move to Chicago when the handsome stranger called and she finally had a name, Ladd Drummond.

When he asked her on a date, she said "yes" with some hesitation as she was all set to leave for the city. Ladd Drummond — a fourth-generation rancher and owner of Drummond Land and Cattle Company — picked her up in a F-250 diesel truck. "At the end of the evening ...I knew there was nowhere else on earth I wanted to be," she said.

Two weeks later, Ladd told Ree he loved her, and they married in September 1996 and twenty-five years later, their marriage is still going strong. Drummond is glad her plans to live in a big city never came to fruition because her life was meant to be just where she was in Oklahoma with the love of her life.