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The Most Shocking Celebrity Breakups And Sweetest Matchups Of 2020

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47. Breakup: Colton Underwood And Cassie Randolph
Colton Underwood and Cassie Randolph met on Underwood's season of The Bachelor, but after a year and half together, they decided to call it quits. 

Underwood said on Instagram, "Its been a crazy few months to say the least, Cass and I have been doing a lot of self-reflecting. Sometimes people are just meant to be friends - and that’s okay. We both have grown immensely and been through so much together - so this isn’t the end of our story, it’s the start of a whole new chapter for us." 

What seemed like an amicable split, became messy real quick. Randolph ended up requesting a restraining order against Underwood, who she said was harassing her and had even put a GPS tracker on her car. They ended up settling outside of course.