A Romantic trip to Colorado takes a windy turn when Jason pushes Tayler, despite her hesitation, to summit Mt. Democrat in 70 mph winds and -19 degree weather.

Jason loves mountain biking; Tayler prefers to read a book; Jason is up for any adventure tossed at him; Tayler likes to be a bit more prepared; Will the adventures that await in Arkansas leave the couple questioning if they have anything in common?

Tayler and Jason travel to Eureka Springs, Ark., a town with a rich history and home to one of the most haunted hotels in America -- the Crescent; Jason convinces Tayler to stay the night.

Jason experiences insecurity about challenges that the couple are dropped into, from falling out of the sky to a rappel into a dark cave.

The couple head to southwestern Oklahoma to climb Quartz Mountain, but when Jason's confidence is shaken during a failed slab climb, Tayler realizes she may need to prepare to carry a larger load on their journey out west.

When everything seems to have gone wrong on their road trip in Oklahoma, Tayler and Jason question their ambitions as they head to Wyoming.