50s Charlbert Headcanon 2: Robert has only ever seen Charley in t-shirts and jeans. Occasionally he’ll wear trousers and a button up shirt, but generally he has the overall appearance of a greaser.
So when Charley asks Robert on a date to the Parker House (perhaps his dad has a banquet there and he has to go, or Charley just really wants to introduce Robert to Boston Cream Pie), Robert was expecting pretty much the same. Until he shows up in front of Charley’s house and sees Charley decked out in a perfectly tailored 3-piece suit and overcoat, and it takes Robert all his has not to jump Charley on the spot.
Suffice to say, they end up renting a room at the Parker House that night.