Before Arie Luyendyk Jr. was named the next Bachelor star, he was wooing Emily Maynard on her Bachelorette season. But Arie was hardly the first (or second) franchise man in Emily’s life — that honor went to Brad Womack!

The Bachelor star met the single mom during his second shot at love on Season 15. With her emotional backstory and Southern belle charm, the blonde beauty won over Brad — and the rest of America — and they got engaged in the 2011-airing finale. Yet, months later, they ended their engagement, leaving fans to wonder what really happened between these two.

Now that Arie is returning to TV to date 25-plus women, we should refresh ourselves on what went down between Emily and her first on-screen ex. Read on for a timeline of their romance.

September 2010 — The First Impression

In their first meeting, Brad couldn’t stop mentioning how “very beautiful” Emily looked in her off-the-shoulder black gown. The feeling was mutual, as she gushed about how happy she was that he was the lead. In their first chat, she told him she had “everything lined up” except for that “somebody special.” Brad then confessed to the cameras, “She’s so sincere in everything that she says so I’m very confident that she’s here for the right reasons.”

Fall 2010 — Their On-Screen Romance

Emily and Brad’s Bachelor “journey” got off to a slower start, as she didn’t get a one-on-one until Episode 3. She further gained his attention in Episode 5's race car group date — where she opened up about her fiancé and NASCAR driver Ricky Hendrick’s death — and on another beach one-on-one in Week 7 in Anguilla. After that, she brought him home to meet daughter Ricki, and days later, they traveled to South Africa to spend the night together in the fantasy suite. Not long after he chose her over Chantal O’Brien in the finale.

Though their love story was picture perfect, in her 2016 memoir, I Said Yes, Emily admitted they lacked chemistry. She wrote, “I liked him. He was warm, kind, sweet, a gentleman… Yet, he wasn’t as funny as I wanted him to be and even though we had a great time together, he always seemed a big uptight.”

November 2010 — The Proposal

In the November-filmed (and March-airing) finale, Brad and Emily went on a helicopter tour over Cape Town. Sometime during that date, he decided he wanted to propose to the 24-year-old over Chantal O.. She accepted his proposal, and the two celebrated their engagement. Then, in the “After the Final Rose” special, fans saw that she was no longer wearing her ring because it “needed to be re-sized” — a telling sign for their relationship.

emily maynard brad womack — abc via getty
ABC via Getty Images

Winter 2011 — The Real-World Relationship

Emily and Brad were open about their romantic issues following the show. Right after the finale aired, Brad admitted it had been “a bumpy couple of months,” and that the two had split a couple of times already. He added, “We've thrown in the towel, broken up. But at end of every day I'd call and say, 'I know you might not like me today, but I love you.’” Emily later revealed Brad tried to end things in an email with the producers, saying “Sorry but things didn’t work out with Emily and I. It wasn’t the fairy tale I thought it would be.”

The root of their issues stemmed from watching the Bachelor season back, and seeing Brad with the other women. Emily explained at the time, “He had a tendency to say the same thing to a couple girls. So I felt less and less special.” That jealousy only worsened when rumors spread that the Bachelor had spent Thanksgiving with his runner-up, Chantal, though he firmly denied the story.

July 2011 — The Breakup

Eight months after the couple got engaged, Emily announced they'd split in an emotional interview with Chris Harrison. Brad didn’t appear in the sit-down, but he did tell People that the “demise of our relationship was completely my fault.” His ex remained cordial, responding that there were no hard feelings and that “just because we love each other doesn’t mean we’re right for each other.”

emily maynard interview — abc
ABC

Fall 2011 and Spring 2012 — The Aftermath

Though their breakup was amicable, a little bit of bad blood did come out in the months ensuing — especially when Emily was announced as the next Bachelorette star in spring 2012. “I think I dodged a bullet with that relationship,” Brad said at the time, adding that he had “no interest” in watching her season.

Both parties quickly moved on to dating others in Bachelor Nation. She got engaged to her Bachelorette winner Jef Holm, and later was rumored to have had a fling with runner-up Arie following their split. Meanwhile, he dated Sean Lowe’s finalist, AshLee Frazier, in 2013. She married Tyler Johnson in Sept. 2014, while, 45-year-old Brad is, by all accounts, still single.