Bachelor Nation first met Brad Womack when he became Season 11’s Bachelor. Brad is famously the only person ever to be the Bachelor twice, returning as the lead for Season 15 after not choosing either of his two finalists on Season 11.

Now, it’s been 14 years since his first season. This week in Bachelor Nation history, fans saw all the drama unfold when he headed to Hometowns with his final four women — Jenni, Sheena, Bettina, and DeAnna — to meet their families.

In hindsight, it might not be shocking that he left the show single. From getting grilled by Jenni’s grandma and facing a very tense dinner with Bettina’s parents to Sheena’s mom already planning their wedding, Brad really saw it all.

From the moment Sheena’s mom Beverly met Brad and saw his relationship with her daughter, she said “the stars lined up” and that she felt “like I’ve known him forever and that he’s already my son-in-law.”

During their one-on-one conversation, Beverly told Brad, “I knew [Sheena] was the one. Whether she’s your one or somebody else’s one, I know she’s the one. I think you guys are great.”

Beverly added, “We are ready to commit. She is ready to commit. She is ready to be one man’s everything. Every mom wants her daughter to be married.”

Before Brad could get a word in, Beverly said, “Let’s get the ring! Move it forward! You would have the best wedding ever. We have a flower girl, we have the bridesmaids. Let’s get the wedding planned!”

But things didn’t go as smoothly with all of the Hometowns.

When Brad met Bettina’s parents, her dad Robert said Brad dropping out of college to pursue his own business as a bar owner was a “great disappointment,” and he was upset about Brad’s “level of education that he has at this point.”

Bettina’s stepmother Anne also chimed in, saying, “Do I like my stepdaughter being hooked up with a guy who runs a bunch of bars? No.”

They continued to grill the Bachelor throughout dinner about working late nights at his bars, and he finally said, “I felt like I was being judged. I felt almost like there was an agenda here. Basically they were asking, ‘Who are you to be with my daughter?’”

Bettina tried to defend Brad to her family, saying, “Some of the most successful people I know in my life don’t have college degrees — including one of your own daughters.”

But her family wasn’t swayed; her dad stood his ground that Brad’s business was “an issue” and he still questioned his education.

After meeting her family, Brad told Bettina, “I might not have education, but I’m intelligent enough not to judge anyone,” and said he was upset that he didn’t feel welcomed by them.

Despite everything they went through during her Hometown, Bettina still received a rose and Sheena was sent home.

And while Sheena’s mom’s dream wedding for her daughter and Brad didn’t come to be, he didn’t end up proposing to any of the other women either.

To take a trip down memory lane and look back at Brad Womack’s first season on “The Bachelor,” scroll through the photos below.