I do like the idea of him having met her at the club. He basically hates this place and that he's back and a good portion of the people there, so I can see him having spent a bit of time there when he came back in 2017. Maybe they met there and, while I wouldn't call them friends, are friendly enough that she gives him constant shit and he just rolls his eyes and has picked her up more than once when she's needed a ride from work. Basically he just sees her as less awful that most.