The 7 Most Intense Two-on-One Dates in 'Bachelor' History
The 7 Most Intense Two-on-One Dates in 'Bachelor' History
Derek Stauffer
Derek Stauffer
Contributing Writer, BuddyTV
They haven't been with the franchise since the very beginning and not every season has included one. However, the Two-on-One date has become one of the most memorable features of The Bachelor (and The Bachelorette.) It's an event that the contestants dread but the audience revels in experiencing. The Two-on-One is typically the point in the season where the "villain" is thrown out and as such, these dates result in some of the most dramatic moments of the series and the franchise as a whole. Here are seven of the most intense two-on-one dates in Bachelor Nation history.


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Kasey Gets a Tattoo ... and Is Left to Freeze to Death

The women of The Bachelor tend to be more responsible for the big dramatic Two-on-One dates. However, the men of The Bachelorette are far from drama-free and innocent. This incident from The Bachelorette season 6 is more notable for how it played out (and what followed) than any of the behavior that either of the men exhibited. 

Bachelorette Ali Fedotowsky took contestants Justin R. and Kasey into a wild winter setting for their showdown. It was hardly the most romantic setting, being austerely white and frozen, but things got much colder when it came time for Ali to cut one of them. 

It's never a good idea to get a tattoo based on a relationship. It's downright insane to get one for a relationship on a reality show. Yet Kasey, to prove his devotion to Ali, got a tattoo for her and she was less than impressed. Kasey revealed the tattoo to Ali on the date and she responded by setting off in a helicopter with Justin and leaving Kasey alone, on a glacier.

Even worse, in the very next episode it was revealed Justin had a girlfriend at home. When confronted by Ali, Justin refused to talk about it, making it seem like maybe Ali should have given Kasey and his tattoo another chance.


Corinne and Taylor's Battle in the Bayou

Corinne Olympios is one of the stranger Bachelor contestants. Corinne was clearly positioned as the villain of the season. Yet against all odds, Corinne became so outlandish and over-the-top that she ended up becoming an unconventional fan favorite. This fits in with the outcome of Corinne's Two-on-One date when she stayed and fellow contestant Taylor went home. 

Even though Corinne came across as a crazy person and severely spoiled, Taylor was a whiny terror on the Two-on-One date. Taylor spent all her time criticizing Corinne about her "emotional intelligence" and seeming supremely condescending in the process. 

The date was awkward but not in a fun melodramatic way. The primary reaction while watching Nick Viall interact with both Corinne and Taylor is a desire that all three would be left in the swamp to slowly be consumed by wildlife. 

 
The Twin Takes out Olivia (in the Middle of the Ocean)

Since her appearance on The Bachelor, Olivia Caridi has been through a bit of redemption. The villain of season 20, Olivia has since become one of the most beloved and funny Bachelor alums, thanks to her live-tweeting of each episode. On the show itself though, Olivia was an over-confident terror. It was no surprise when she was chosen for a Two-On-One date by Ben Higgins to be accompanied by one of the Ferguson twins, Haley or Emily (it doesn't matter which one.)

No matter which twin accompanied Olivia, they were determined to take her out on the Two-on-One. It's a task that they succeeded in by exposing to poor, innocent Ben some of Olivia's more outrageous behavior in the house. 


Left with few options that wouldn't make him seem like a total idiot, Ben dumped Olivia on an island. Then Ben proceeded to get in a boat with the twin, leaving a devastated Olivia to weep as massive waves crashed all around her. 

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Alex and Chad's Wilderness Showdown

Chad Johnson is one of the most infamous villains, not only from The Bachelorette but Bachelor Nation as a whole. Chad, whose Bachelor journey ended with him getting so drunk during Bachelor in Paradise that he soiled himself and had to be removed from the series, made his villainous name on Bachelorette season 12. 

All the men in JoJo's season of Bachelorette hated Chad and it all resulted in him going on a Two-on-One with one of his biggest rivals, pint-sized former Marine Alex. The date occurred in the middle of the Pennsylvanian woods and it was, for all intents and purposes, shot like a horror film. It was obvious Chad was going out but it was unclear when, and how much damage he would do before that happened. 

The highlight of the date was right before JoJo sent Chad packing. Left alone, Alex and Chad had a bizarre exchange of idioms. The two guys couldn't stand each other and were so close to punching each in the face. Yet all they could do was swap bizarre phrases like "Life ain't all blueberries and paper airplanes, you know what I mean?" and "Hay's in the barn." Toxic masculinity at its finest. 

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Kendall and Krystal's 'Heart-to-Heart'

Krystal is the most recent villain in Bachelor history but it's easy to see her going down as one of the most infamous. Krystal was a nightmare on The Bachelor season 22 and there was every reason to expect her Two-on-One date with Kendall would be just as explosive as Krystal's many personalities. The date was intense but not for the typical Bachelor reasons. 

Krystal, like many villains before her, tried to throw Kendall under the bus by suggesting to Arie that Kendall wasn't ready for marriage. The ploy, however, blew up in Krystal's face as Kendall learned about it immediately. Instead of attacking Krystal, Kendall just told her she felt sorry for her and that is unhealthy to lash out others. Krystal, with her confrontational drama queen brain, couldn't handle someone being a mature and empathetic person and she just stared at Kendall. It was unclear whether Krystal's head was going to explode from the effort or if she would just lash out even harder and physically attack Kendall. 

This confusion lasted the rest of the date until Arie, mercifully, cut Krystal. Krystal proceeded to watch the two of them leave, like a femme fatale in crappy James Bond movie. 



Lee's Confident and Racist Lies About Kenny

Two-on-One dates can get tense but usually they're all in good fun. This was not the case in Bachelorette season 13 when Rachel took Kenny and Lee on their Two-on-One. 

Throughout season 13, Lee had done some and said some very questionable things, most of them based in racial prejudice. On the Two-on-One date things boiled over as Lee casually and confidently lied about Kenny attempting to pull him out a van and attack him. 

When Kenny learned of the lie he confronted Lee but, cowardly, Lee denied it. Lee lied as easily as he had when he first confessed to the big "fight." It was awful, cruel and crossed about every line that can be imagined. Kenny didn't end up decking Lee, before the latter was eliminated, but he would've been more than justified in doing it. 

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Ashley I. and Kelsey's Two-on-One Badlands Break-Up

The crown jewel of Bachelor Two-on-One dates is the confrontation that happened between Ashley I. and Kelsey Poe during Chris Soules' season. The setting, the outcome and the ladies involved resulted in a perfect storm of Bachelor trashy showmanship. 


Before Kelsey made it to the Two-on-One she was already causing trouble by talking (non-stop) about her dead husband. Yet on the date itself, which with a true lack of subtlety, happened in the Badlands, every weird and unusual thing about Kelsey came out, courtesy of Ashley I. 

Yet even though Ashley I. wasn't the villain, Bachelor Chris Soules wasn't too impressed with her either. After having Ashley I. deal with a scary and vindictive Kelsey, Chris decided to break up with both Ashley and Kelsey, in that order. The two ladies who despised one another were left in the Badlands with no one but their crying selves for company. 

Obviously they survived as Ashley has gone to cry on every show in the franchise but The Bachelorette. How they made it out without killing each other is anyone's guess. 



What do you consider some of the most memorable Two-on-One dates from the Bachelor franchise? Did we miss any big ones? Where would you rank these dates?

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