I think you answered your own question, Rilchiam.
The conversation between Simon and girl with the pink flowered dress went something like this:
Simon: What would do with the money?
Pink Girl: I think I would buy a Thunderbird, vintage model, convertible. But I want it in pink. I would look so cute in that.
Simon: Honest answer. I like that.
In comparison, the conversation between Simon and the “Isn’t She Lovely” guy went something like this:
Simon: That was good.
ISLG: Simon, that was great… (random bullshit ~ BIG mistake)
Simon: (put off now because ISLG wasn’t humble about the praise) No, it was good. Not great, good.
ISLG: (more random bullshit)
Simon: (sniffing for trouble) What would you do with the million dollars?
ISLG: I would give 100 000 to charity …
Simon: (thinking, bullshit but that’s the standard 10%, give him a chance)
ISLG: Then I would take 200 to put aside and live … (presumably off interest, which wouldn’t pay that much)
Simon: (thinking, not only is he a bad bullshitter, he’s dumb)
ISLG: Then I would take some more and put in charity.
Simon: (thinking: Ok that’s it) NO!
The guy can’t think on his feet. If I were investing in someone, he’d have to show me some kind of business sense. He was “good”, not great. Could have been great with time. But just not smart enough for this cut throat business. Pink Girl didn’t have to think on her feet so much, cause she was honest. Probably not smart for a cut throat business either. But in this case, it wasn’t a question that warranted a huge fabrication.
ISLG said as he was walking out of the building, “That question’s gonna haunt me for the rest of my life.” He’ll be searching and searching for what the RIGHT thing was to say. In fact, the RIGHT thing to have said was right after Simon said, “That was good.” And the RIGHT thing to say at that point was ABSOLUTELY NOTHING except “Thank you”.
As for the cheerleader, “nice girl, pretty girl, good singer, good dancer…can’t possibly win this competition” I think I know where he’s going with this. Usually someone who is good at everything is great at nothing. And usually someone who is great at something, really sucks at something else. But the same seems to apply to Scooter Girl, yet she had practically a whole segment dedicated to her.