On this episode of Ruin Your Night, Caitlyn talks about her trip to Chicago and all the fun that ensued. Then, the girls move onto a new segment they're calling "Cuestions & Janswers", where Caitlyn asks Jess totally normal questions that surely won't make you question her sanity. Jess may or may not have regretted agreeing to it. Special guest appearance by Jess's boyfriend, who well, is used to their quirks and just goes with it. Grab a drink, lower your expectations, and enjoy!





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