The Weirdest Dates in Bachelorette History

Jenn Tran’s season of The Bachelorette kicked off on Monday, July 8 with a dramatic premiere. Next week, Jen will go on her first dates with the men. While we wait to see what the dates will entail, let’s take a look back at some of the most memorable dates in the show’s history.

Here are the weirdest Bachelorette dates of all time…

Desiree’s rap video, a very weird date

In Season 9 of The Bachelorette, Desiree Hartsock and her suitors were joined by rapper Soulja Boy to create a rap video. The season wasn’t exactly diverse, which made the date feel pretty awkward. None of the contestants were good at rapping or dancing, so it was a snooze. While it was cool to have a celebrity on the show, the date itself was a bad idea.

Ashley’s roast, particularly weird date

Ashley Hebert’s roast date went down in infamy as one of the worst Bachelorette dates of all time. Typically, the lead is held up on a pedestal. Contestants shower them with compliments and profess their undying love to a woman they met a few weeks ago. But in Season 7, Ashley was hung out to dry. Producers decided it would be “fun” for the contestants to roast the Bachelorette. While it may have sounded like a good idea, in theory, the execution was horrific. The men made comments about her body, dating history, and hurled several other insults at her in the name of “comedy.” One contestant even called her “another man’s trash.” It was brutal.

JoJo’s stand-up date, super weird

In Season 12, JoJo Fletcher took her men to a local LA theatre to perform stand-up comedy. The men were asked to tell a raunchy story about their love lives in front of the woman they are trying to marry. If that wasn’t uncomfortable enough, one of the contestants used his set to imply the cast villain, Chad Johnson, suffered from erectile dysfunction. The comedy bit appeared to make everyone uncomfortable and upset the short-tempered villain. It was hard to watch.

Hannah’s bungee jumping date, no thank you weird

In Season 15, Hannah Brown surprised contestant Garrett Powell with a naked bungee jumping date. It was a bit intense for a first date, especially since there wasn’t much chemistry between the two. The outing also sent contestant Luke Parker into a jealous rage, which viewers didn’t love.

Kaitlyn’s mock wake, immediately no weird

Kaitlyn Bristowe played dead during a group date in Season 11. The Bachelorette lay down in a coffin while the men mourned their fake dead girlfriend. It was so odd. Kaitlyn couldn’t stop laughing and the men seemed confused by the premise. It wasn’t a home run for the franchise.

Rachel’s mud wrestling date, eye-roll weird

Rachel Lindsay’s men had to get down and dirty during a group date in Season 13. The mud wrestling date is often regarded as one of the worst group date ideas in the show’s history. It wasn’t sexy and it reminded us how truly insane the show can be. How is a mud wrestling victory an indicator of who will be a good husband?

Clare’s strip dodgeball date, just weird

Clare Crawley’s strip dodgeball game was a total disaster. During the date, host Chris Harrison revealed that the losing team would be fully nude by the end of the game. While the comment was meant to incentivize the contestants to be competitive, it wasn’t received well by viewers. Fans pointed out that producers would never ask women to be fully nude on television. It felt like a double standard. To make matters worse, the concept upset contestant Yosef Aborady, who wasn’t even on the date. He called out Clare for the date and said he wouldn’t want his daughter to see him stripping on television. It was so awkward.

Rachel’s spelling bee date, wholesome weird

Rachel Lindsay’s season featured a spelling bee that didn’t go so well. The idea felt like a ploy to humiliate the contestants. They missed easy words and had to spell some dirty words as well. The point of a group date is to bond with the Bachelorette but on this date, Rachel sat off on the sidelines, judging the men’s unfortunate spelling abilities.

TELL US – DID WE MISS ANY WEIRD DATES? WHAT DO YOU THINK IS THE WEIRDEST DATE IN BACHELORETTE HISTORY?

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