Bosko should have stayed in bed!
The short opens with Honey trying to teach Wilber to play the violin. He's 'playing' "In the Shade of the Old Apple Tree"-mangling it is probably closer to being an accurate description. Wilber is particularly obnoxious here and Honey decides to call up Bosko, who is sleeping, so his dog Bruno answers the phone and then wakes up Bosko so he can talk to Honey on the phone. She invites Bosko over.
The best part of the short is Bosko riding over to Honey with Bruno following. The different events which take place on the bike ride are ultimately most of the highlights of the short, so I won't spoil them here.
When Bosko gets to Honey's, he hears Wilber's scratchy attempt on violin and then pulls out a saxophone (watch this scene closely) and plays the same notes better than Wilber can manage. Honey then comes out and she and Bosko do a number, Bosko playing and Honey singing, until Wilber douses Bosko with a tub full of water.
Then comes a sudden shift-the last part of the short is the "date" in the title. It's a picnic, which is essentially rained out. Though there are some decent gags in the last minute and a half or so of the short, it feels almost tacked on in order to justify the title. It's largely anticlimactic and not terribly interesting.