You witnessed him getting slapped for trying to flirt with a pretty girl after holding the door open for her, and you couldn't help but wince. He smiled and gave a charming grin after, but as he walked into the Happy Tree Bar™, he looked sullen. You knew why he was here.
"Hey... the usual, sugar," He said with a small smile and a wink, but he was so obviously out of it. He just glanced to the side and leaned back in his chair as he moved a hand to rub his cheek again, before his eyes slid back to you.
"...Make it double."
You just stared at him, giving a look like, "really?" But you couldn't blame him I guess. He's had a rough time.
As you went off to make it, he just laid his head on the table and watched you, looking just slightly defeated. He's had a lot on his mind lately, he was so tired.
He couldn't help but think about how lonely he was. It was miserable... He used to have girls all up on him back in his prime, but... Geez, he's not even that old, but he sure felt like it.
He missed when he was charming.