One of the most-dreaded outings on The Bachelor is the two-on-one date. The producers use this opportunity to throw two women together and have them compete over one rose. Two will enter and one will be sent packing, so Bachelor two-on-one dates are always super dramatic. Not only are the women both trying to get the one rose, but often the date will feature two women who hate each other.
Even having your name selected for a two-on-one is basically a death sentence. Former Bachelorette Ali Fedotowsky said that on her season, she let the producers pick which one of the men stayed because she didn't care about either of them. She went into detail about the tricky date in her E! News Bachelor blog.
You either know who you are sending home before the date or you bring two people you're not into at all so you don't care who goes home. Think about it: Why would you ever bring two people that you really like, knowing you have to send one of them home? Makes no sense.
So, it's not usually a good thing to be invited on a two-on-one, but that doesn't stop it from being a dramatic date to watch. Through all the seasons of The Bachelor there have been a number of crazy showdowns between the two chosen women. So, while not every season contains this infamously terrible date, I've ranked the 11 of them from least to most dramatic. Can you guess which one made the top of my list? Read on to find out.
Jesse Palmer - Mandy J. & Trish (Season 5)
Back in Season 5, the two-on-one dates worked a little differently. There were still two women on the date, but it wasn't a one-rose-only situation. Instead it functioned as a smaller group date, but the women would still be up for roses during the ceremony later that week. Jesse took both Mandy and Trish on his two-on-one, and he spent time kissing each lady during their brief alone time. At the end of the week they both got roses. Oh how things have changed since the early and simple days of the show's beginning.
Brad Womack - DeAnna & Jade (Season 11)
Jade and DeAnna were known to not get along when~surprise~they were both selected for the two-on-one date. It was a pretty standard date, and it was clear DeAnna and Brad had more chemistry. When Jade was eventually sent home she lamented that she let her conflict with DeAnna get in the way of her time with Brad. (Isn't that how it always goes on these dates?) The most dramatic part of the date was when Brad sent Jade home and then proceeded to make out with DeAnna in a hot tub as Jade walked away. Awkward!
Matt Grant - Marshana & Holly (Season 12)
No one was more shocked by Matt's two-on-one choices than Holly herself. She had been the recipient of a one-on-one date the previous week and was surprised to be going on another date so soon. "Honestly I thought, 'Maybe he just wants to spend more time with me and it's an easy way to get rid of somebody else,'" she said after the show.
But Matt shocked fans everywhere when he sent Holly home and kept Marshana, despite their limited time spent together. "Marshana hadn't spent any one-on-one time with him, had not received a kiss," Holly said. "I thought for sure that I was staying." But as is sometimes the case on Bachelor land, overconfidence eventually leads to disappointment and Holly was sent home to her surprise and that of the fans. These darn Bachelors are so unpredictable with their choices sometimes.
Jason Mesnick - Nikki & Stephanie (Season 13)
Nikki really struggled with the idea of competing against Stephanie because Stephanie was also a single parent and Nikki felt like she and Jason were going to bond over that. Then when it came time for the ladies to dance with Jason, Nikki was dismayed that he and Stephanie were tearing up the dance floor together.
In general, Nikki was a real Debbie Downer about the date and ended up sabotaging herself when she waited to tell Jason about her previous 11-year-long relationship. He seemed upset that she hadn't shared that earlier since it was obviously such a huge part of her life. In the end Nikki's prediction came true and she was sent home. Although I can't help but think if she were a little more honest and a little less negative, things could have gone differently.
Andy Baldwin - Peyton & Tessa (Season 10)
Andy sent Peyton home on this date when he realized his chemistry with Tessa was stronger. Then poor Peyton was forced to watch Andy and Tessa take off in a helicopter together while Peyton was left stranded on the deck of a ship. (Who knows? She could still be there today.) It wasn't super dramatic as far as eliminations go, but the send-off with Peyton watching the two of them fly off together made the date a little heart-wrenching.
Ben Flajnik - Blakeley & Rachel (Season 16)
As per usual, the producers sent along two women who didn't like each other to draw in viewers. During the dancing portion of the date, Blakeley drew upon her sexuality to try to captivate Ben, while Rachel slut-shamed her to the camera. “I think Blakeley is f***ing tacky,” she said while Blakeley was dancing with Ben. The Bachelor called his two-on-one "excruciating" because he dreaded having to hurt one of the women's feelings.
But it was excruciating for so many other reasons too, mostly because Blakelely had a meltdown when she was sent home. Ben sat there awkwardly while she sobbed about having to leave even though she'd opened her heart up to him. (Earlier in the evening Blakeley showed Ben a scrapbook she'd made of what their life could be like if she was his wife.) It was all a little much for him and for viewers, so I'm not surprised she was eliminated.
Brad Womack - Ashley S. & Ashley H. (Season 15)
For his second season and second two-on-one, the show thought it would be entertaining to send two Ashleys along for the ride. (Maybe Brad thought it would be easier to keep them straight since they both have the same name?) But even worse than Ashley Hebert and Ashley Spivey sharing the date and their names, was the fact that they were also best friends.
"Maybe this is kind of messed up for me to say this, actually, you know, I was more in love with Ashley H. than Brad," Ashley Spivey admitted to Wet Paint after the show. She said the two-on-one was very difficult "because if Ashley H. got sent home, who was my best friend in the house, I would just be completely distraught," Spivey said. "But then, however, I’d be really broken-hearted if I got sent home, ‘cause I was looking forward to getting to know him better."
It was just a lose-lose situation either way and both ladies were sad when Ashley S. was sent packing.
Jake Pavelka - Ella & Kathryn (Season 14)
Jake became the first Bachelor in history to send both of the women on the date home. The break in standard protocol shocked viewers, and the ladies on the date who were both confused. But Jake just wasn't feeling it with either of them, and he sent them packing even though nothing particularly crazy had gone down.
Sean Lowe - Tierra & Jackie (Season 17)
The Season 17 villain was Tierra so of course the producers sent her on the two-on-one date. She was joined by Jackie, who couldn't stand her. Jackie made the age-old mistake of telling Sean what she thought about Tierra. She was very diplomatic about it saying, "I would hate for you to fall in love with somebody who's not their true self."
But in the end, the warnings didn't matter. After Tierra told her sob story about her ex who was in and out of rehab, Sean sent tattle-tale Jackie home and kept Tierra much to the dismay of the house. Later when he reflected on the date, Sean said he wished he'd kept Jackie around instead because he felt like Tierra "duped" him.
Byron Velvick - Heather & Mary (Season 6)
ABC decided to really change things up for Byron's two-on-one and they made it a blind date with two ladies from previous seasons. Byron opened a mystery door to discover Heather from Season 2 and Mary from Season 4. Then both women had a brief chance to speak with him before the impending rose ceremony. Though neither woman was eliminated during the two-on-one blind date, he sent Heather home during the rose ceremony and kept Mary. (Good thing too, because he ended up choosing her as the winner of the season.)
The surprise aspect of the two-on-one was interesting, but was lost a bit on Byron because he'd never seen The Bachelor before and didn't know either of them. But I think it's pretty dramatic to bring in two contestants from former seasons for a mystery two-on-one, so ABC should consider that strategy again in the future.
Chris Soules - Kelsey & Ashley I. (Season 19)
The most recent Bachelor season truly carried with it one of the most dramatic two-on-one dates ever. Although the word "dramatic" is thrown around lightly on the show, this date embodied the essence of the word in every sense. Not only were two of the season's most-controversial women brought on the date, but they were both sent home. It's only the second time in Bachelor history that both women on the two-on-one were eliminated.
It wasn't just that which made it crazy to watch, though. Watching Chris probe Ashley for information about Kelsey and then running back to tell Kelsey what Ashley just said was a move that shocked even host Chris Harrison. Chris Soules basically threw Ashley I. under the bus and then left both ladies on a bed together in the middle of the desert. "I know what you did," a menacing Kelsey told Ashley who didn't respond and calmly took a sip of her wine.
You can't write that kind of drama, and when it all culminated in Chris flying out of the canyon in a helicopter while leaving the two women stranded—it was reality television gold. I feel bad for the ladies that they had to endure such an obvious set up (the producers knew they would butt heads), but I can't deny that it made for extremely dramatic television.
Images: ABC screengrab (4); Getty Images (5); Rick Rowell, Craig Sjodin, Isaac Brekken/ABC