The Bachelor season rankings: All Bachelor seasons ranked

4 and 5: Brad Womack: Season 11 and Season 15

Brad Womack was lucky enough to be the Bachelor not once, but twice. His journey is a riveting one which left Bachelor Nation puzzled over their thoughts of him. In his first go-around as lead, Womack joined season 11 with high hopes of finding his one true love.

However, his season ended with him picking…no one at all. Yes, that’s right, no one. He became the first Bachelor to ever reject both finalists, and it left viewers scratching their heads and in total shock and awe over his decision to do so.

DeAnna Pappas and Jenni Croft were the final two women in Brad’s first season and were quite confused over his decision to leave the season solo. Back in 2007, it was quite a controversial way to end an entire season based on the premise of finding your life partner.

As luck would have it, Brad Womack got another shot at being the Bachelor in season 15, and this time around, he did get down on one knee and proposed to winner Emily Maynard. Unfortunately, the pair didn’t last very long, creating yet another unsuccessful Bachelor Nation engagement. Side note: Does anyone have statistics on the number of couples that actually make it long-term? I’m rather curious about this!

During this summer’s The Bachelor: Greatest Seasons Ever, Womack’s journey on The Bachelor was revisited in all its awkward, gut-wrenching glory. But Womack stopped by with some great news for Bachelor Nation–he’s been in a relationship for the last three years with girlfriend Jena Mays–and boy, are they adorable!