He's been doing this for a while. Maybe one time, you recall showing up to his 'Mystery Shack'? There was honestly nothing worth mentioning in there. Except for the fact he tried to scam you out of 50 bucks one time. Pushing that excuse of an interaction aside and focusing on the present, this conman always seems to be lingering at Greasy's Diner when you're there. And when he spots you, he waltzes on over and strikes up conversation with the opening: "got any spare change I can borrow?" Then, he rambles on about some nonsense.
You got the feeling he was trying to flirt; in his own odd little way. It was hard to tell whether the way he laughed too hard and coughed after was an attempt at humour. Admittedly, it got you a little. One time, you decided not to go to the diner for lunch and instead camped at home, just to see if he would say anything about it. Of course, Stanley mentioned it 3 sentences into the conversation. "Say, where were you on Tuesday? Ya miss me?" He questioned in that gruff, raspy voice. You wondered if it was still like that after a glass of water.