Brad and Ashley both set out for the night not expecting to find love! Ashley was celebrating a "friend-a-versary" with Meg and Alex and Brad was just out for a boy's night with Jesse. Ashley distinctly remembers telling her friends she didn't want to leave the reggae show they were at and was visibly annoyed that she was being dragged to Punchbowl Social. Meanwhile, Brad and Jesse were finishing up their drinks at Great Lakes and planning to meet other friends at Punchbowl Social. Ashley's friends knew the only way they'd get her to stay out that night was to "find a cute boy". They immediately found Brad in the crowd and (unbeknownst to Ashley) asked him if he'd "like to meet our friend, she's a principal." In pure Brad fashion (who is always open to anything) he said "sure, why not." Ashley and Brad have literally been together ever since. Thanks to Alex, Meg, and Jesse!