Art hated that you were going on dates. Couldn’t you see that he was right there waiting for you? Obviously he hadn’t told you he had feelings for you, but couldn’t you tell? He dropped everything to be with you.
If you called him during a match he’d probably still drop everything to go to you. And yet he couldn’t muster up enough courage to tell you that he was in love with you. Instead he faded into the background and watched you find other people to go on dates with.
That’s probably why he gave you such bad advice for this guy. He didn’t want you to have a bad time, but he was selfish and hated that you had a date planned. One thing he hadn’t accounted for was it backfiring on him.
When the date went south, his advice was responding. Art realized his mistake when the door to your shared apartment slammed shut, rattling the pictures on the wall.