The Bachelor: Greatest Seasons Ever: The weirdest moments from Brad Womack’s seasons

The Bachelor: Greatest Seasons ever looks back on Brad Womack!

The Bachelor: Greatest Seasons Ever took us back to an interesting moment in Bachelor Nation’s history–to the very first Bachelor who do it twice. Brad Womack was back on our television screens Monday night as we had the chance to relive the glorious sexpot and his double down journey to find love.

Taking it back to 2007

Yes, Chris Harrison took us to 2007 where Brad found not one, but two women he sorta, maybe thought were “The One” only to break both of their hearts at the last second in, of course, dramatic fashion. Bachelor Nation was not happy, but that didn’t stop Brad from reopening that heart wound and taking another shot at disappointing America by dishing out roses once again.

There was weird, there was awkward, and there was just plain badness. Let’s see what memorable moments made Brad’s seasons so great.

Webbed toes, dirty talk–and more

It’s no surprise that the weirdness always pops out on night one and Brad’s first round of ladies definitely brought a little bit of the crazy. We had the girl with webbed toes who decided to put her foot up on the table to display her unique features. A fun party trick! We had the girl who stripped down to a bikini and took a dip in the pool. At least she came prepared?

And who could forget later on in the season when Hillary Reisinger went on a dirty talk rampage and told producers in full detail everything she wanted Brad to do to her? Hillary, this is a wholesome show about true love! Keep those thoughts to yourself. Or at least off of national television where you know your mother is watching.

The one where Jenni Croft AND DeAnna Papas are dumped

Worst moments wise, it is hard to not pick Brad dumping Jenni at the final rose ceremony, but somehow our boy Brad made it much worse when he struggled to break-up with DeAnna immediately following round one of emotional trauma.

Things started out fine and then Brad needed a moment and had to walk away from the floral surrounded platform aka he started heavy breathing and slightly hyperventilating at the idea of crushing not one, but two women who were clearly in love with him. It was awkward AF and I felt terrible for poor DeAnna who had to know the rest of this moment would not go well. (P.S. it did not.)

DeAnna was heartbroken and confused and asked our Bachelor if he really only got friend vibes from the relationship. He said no, but that he couldn’t love her like she needed and it was time to say goodbye. And America had a new enemy.

The slap heard around the world

Weird moments the second time around also happened quickly when Chantal O’Brien came in super hot and started night one with the slap heard round the world straight to Brad’s face. It was amazing and much appreciated by Bachelor Nation. And to be honest, only helped her chances as she made it all the way to the top two.

Madison Garton also challenged the norm with her very, very pointy fangs that seemed to bother everyone except her. Brad was confused and scared and did not recall putting “vampire” on his list of ideal qualities in a significant other. The nightmare was short-lived, however, and she was sent back to her haunted castle.

Michelle Money

The worst moment was not a moment, but yet again a whole person who ruined everyone’s day. Michelle Money was a woman to be reckoned with as the most aggressive lady in the mansion who stole Brad from anyone at anytime. Not to mention when she locked him in a room, sat on his lap and sucked on his face as she threatened him that he needed to send other girls home ASAP. Yikes.

The psycho was endearing for a while until Brad saw too much of his own crazy reflecting back in her spinning eyes and Michelle did not receive a rose and pouted her way to the limo where she refused to speak and instead laid down for a little post break-up nap on her journey home. Sweet dreams, Michelle!

We are off again next week, but tune in in two weeks for Ali Fedotowsky’s season of The Bachelorette.

Are there any moments we missed from Brad Womack’s episode of The Bachelor: Greatest Seasons Ever? Share with us in the comments below!