Thanks, friend! I hasten to disclaim any credentials as a Shakespearean, but I suspect that your prompt may be the set-up for the first meeting of Sir Andrew Aguecheek (the most hapless person!) and whoever it is whose existence allows him to say “I was adored once too.” I like imagining Sir Andrew as a good tipper. I like to think things work out for him, in the long run. He is, obviously, pretty oblivious, but unless I’m forgetting something, he seems far kindlier than Sir Toby.
To more properly answer your question: unlike many of the Shakespeeps around here, I don’t do modern AUs, but, if I were to try to make that prompt work for Henry and Cate, he’d be the bartender, while she’d be fed up with parental expectations and also Men Generally. If for Beatrice and Benedick, she’d be the bartender (obviously) and kind of annoyed by how attractive she actually finds him, even when he’s sloshed.