What The Pioneer Woman's First Date With Her Husband Ladd Was Like

Ree Drummond, better known as Food Network star "The Pioneer Woman," has been married to her husband Ladd Drummond since 1996. Theirs is one of those special partnerships that has done more than just stand the test of time. Over the decades, their marriage has flourished into an empire. Drummond Ranch, their Oklahoma abode, is more than just a home: It's also a place for Drummond to shoot her show, and a sprawling agricultural estate, too — over 400,000 acres of Osage land, to be exact.

Long before the ranch life with their five children, there was a first date memorable enough to set the stage for everything to come. The Drummonds' story began at a local bar in Oklahoma, not long after the Pioneer Woman returned home from living in Los Angeles. After graduating from the University of Southern California, she was fully preparing to move to Chicago. That's when fate intervened.

One evening, a young Ree Drummond glanced across the bar she just so happened to be at that night. Her eyes caught something she never would have seen back in LA or northeast in Chicago: A tall, strong, and mysterious cowboy. That cowboy, sipping a bottle of beer and dressed in jeans and boots, would later become her husband Ladd Drummond. Ree opened about the chance encounter in a 2017 issue of The Pioneer Woman Magazine (via Country Living): Their connection was immediate, and the two talked for hours that night.

Despite the instant chemistry, it would take four months for Ladd to finally call Ree and ask for an official first date. (Little did he know that this one phone call would mark the beginning of something monumental: the future Pioneer Woman brand.) On their first date, Ree experienced a moment that would change her life forever. She remembers their first kiss vividly, saying, "I don't know how long we stood there in the first embrace of our lives together. But I do know that when that kiss was over, my life as I'd always imagined it was over, too."

Fast forward to the present day, the Pioneer Woman and her husband, Ladd Drummond are still going as strong as ever. The couple has five children, including their foster son Jamar, and the two have cultivated a life filled with love, laughter, and lots of good food along the way. Their epic journey together — from that heart-eyed first meeting in an Oklahoma bar to raising a family and building an empire — is a testament to their enduring bond.

In September 2023, Ree Drummond shared a story on Instagram from a date night that showed off that same lightheartedness that first brought her and her husband together: While out at a restaurant, the pair had a small disagreement over onion rings or fries, which ended with them both sharing each other's sides. (Some things never really change, do they?) And to think: It all started in a small town bar with an unmissable cowboy and an unforgettable kiss.