Former Bachelor Brad Womack had two seasons to find love filled with tons of eligible ladies. Who did he choose? Deanna Pappas and Jenni Croft both left heartbroken during season 11 along with Chantal O’Brien in season 15. However, Emily Maynard managed to steal the leading man’s heart … for a bit. Take a look back at his journey below. 

Brad was a 34-year-old winemaker when he appeared on the franchise the first time. The finale left Deanna and Jenni — and fans at home — scratching their heads. He first eliminated Jenni, which left Deanna as the last contestant standing. Surprisingly, Brad admitted his feelings weren’t strong enough to continue things off-camera and broke things off with the Georgia native. 

Brad Womack and Deanna Pappas During the Bachelor Finale

The restauranteur’s decision is still puzzling to Deanna, who went on to become the Bachelorette during season 4 and is now happily married to Stephen Stagliano, whom she did not meet on the show. 

“I was the girl that everyone thought he was going to choose. And then at the last minute, he decided not to choose anyone and that really shifted the way the franchise works,” the Bachelor Nation babe told Us Weekly on the “Here for the Right Reasons” podcast. “I remember saying when all of that stuff happened, like, I was so confused, I don’t know why he did all of this, but now it means so different to me, because had he not done that, it would have changed the really the path of life that brought me to where I am now.”

However, that wasn’t the end of Brad’s journey. He took the reins of season 15. Many notable contestants from the franchise were featured, like Emily, Chantal, Michelle MoneyAshley Spivey and Ashley Hebert, who became season 7’s Bachelorette

Brad Womack and Emily Maynard on The Bachelor
ABC/Rick Rowell

He proposed to Emily during the finale, but they split eight months later. After leaving the show together, the reality pair had “a bumpy couple of months” at the beginning, Brad admitted at the time. “We’ve thrown in the towel, broken up. But at the end of every day, I’d call and say, ‘I know you might not like me today, but I love you,’” he said.

Brad told People their “demise” was “completely [his] fault.” The West Virginia native also confessed watching the show back made things difficult. “He had a tendency to say the same thing to a couple girls. So I felt less and less special,” she expressed. 

Emily became the Bachelorette during season 8, but broke things off with winner Jef Holm shortly after. She is now married to Tyler Johnson, whom she met at church.

As for Brad, he still appears to be single and stays busy with his booming career as a bar and restaurant owner in Austin, Texas.

It’s been a wild ride!