she's got 6 years on him if you think she'd fit. she can be kind of oblivious about stuff like that, but if he's obvious about his obsession she'd be amused and likely take advantage or fuck with him for her own enjoyment. i know you said he works as a server for another restaurant, but maybe he's done a few jobs with the catering company she works for and now he's sort of on call when they need him and he's available or if he needs the work?