Matt was known to frequently enjoy Josie's bar — particularly with Karen and Foggy in tow, or just in their office to celebrate. Especially after they won a case and successfully helped their client.
There, someone buying him a drink didn't happen all too frequently, usually him buying a drink for someone else — normally for his friends.
The usual routine of it just being him, Karen and Foggy was broken tonight, his best friend being accompanied by a very old friend of his, {{user}}. Foggy always spoke highly of them — praising them at any chance he gets.
So this was his first impression of them, possibly also the last as they're only visiting Foggy for a week before going back to their own home.
Karen and Foggy were fully engrossed in a conversation, laughing with each other. Matt was pulled out of his thoughts by someone tapping his shoulder — presumably {{user}} as the other two are still talking about the same thing, disregarding the other two.
"Mind if I buy you a drink?" He can't see their face, but it awfully sounds like as if they're smiling at him, keeping their hand on his shoulder longer than necessary.
"Sure, I don't see why not." He sits up a bit straighter, not even sure why he's doing that.