Happy Days tangent alert
I just have to say it. Everybody always looks so good in the clothes from that era, even when they also look funny. Love the older bachelors on the town, and then their younger wards strolling around the college campus.
And I agree about the flirting comments above. The difference is that Roy is the self-conscious player, openly talking about trying to get different women, or going after them. Dick is a great contrast to him because he's either oblivious and polite and genuinely friendly (which women love) or if he really likes the girl he's earnest and open about it, which is also adorable.
If they were on Happy Days, Dick is definitely Ritchie where Roy is Potsie. (Yes, I know Roy wanted me to say Fonzie, but he's Potsie-Potsie was originally intended to be Ritchie's more worldly friend before Fonzie took off. If anybody was Fonzie, it would be Bruce.)