If you don't want to go this direction, please feel free to veto this. You know me - I'm easy to accommodate. XD
Unfortunately or otherwise, here is someone he does know, at least a little. Laurel doesn't come to the bar often (at least not without Ivy, the time or two they've been), but she feels like she could use a drink after a particularly long day. She had several customers from hell in a row, and her retail smile was wearing a bit thin, by the end.
She doesn't see him right away, mostly because she's not expecting to. But her older self, the one she dreams about, has been closer to the surface since her encounter with Gary, and there's a twinge of recognition, then echoed by her actual recognition. She actually feels relieved to see him, first, then a bit worried since he looks upset, then finally uncertain. Where they left things, saying hello should be fine, but for some reason she hesitates.