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3. Ashley I. and 4. Kelsey Poe

The Bachelor
Ashley I. and Kelsey Poe on The Bachelor | ABC

This two-on-one date went terribly, but it is also one of the most memorable moments of the show! In Season 19 the two went on a date with Chris Soules in the Badlands. There, Ashley spent her alone time with Chris telling him that the rest of the girls think Kelsey is fake. Chris then went to spend time with Kelsey and told her everything Ashley said. This led to some very awkward alone time between the girls before Chris hopped in a helicopter and left them behind.