Bart and Cheryl actually met on a blind date, set up through their mutual friend Lisa. Bart surprised Cheryl with a not-so-traditional first date: an “Old School”-themed party where he was the featured guest, Frank the Tank. Through the time they were dating, they continued to have fun together- dressing up as the SNL Spartan Cheerleaders for Halloween, heading to Key West for Fantasy Fest, and organizing New Years Eve parties and pub crawls for their friends. Bart proposed, to Cheryl’s surprise, while on vacation in Playa del Carmen, Mexico on a rooftop deck overlooking the ocean.