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I’d suggest another reading into Rashi’s words:
The gentile was asking for the rule that sums up the whole Torah. What he was thinking was that there is an underlying rule that once you know that, everything else is understood by itself. In reality there is no such thing. When you give a child five rules about something, they can often be consolidated into one idea, to an adult. The Torah comes from a “place” much higher than any Malach can perceive. How can you expect to be able to give one concept that would de-necessitate the whole Torah?
When you look at the rest of that Gemara, you see a few stories of how people came with certain assumptions about the Torah and Mitzvos. In all instances, Shamai didn’t accept them because they had the wrong notion of what Yiddishkeit is all about. Hillel, knowing that once they are exposed to the Torah in a real way they’ll come around, tricked them by having them think that he’s accepting them on their terms. Once, they integrated, they understood what their mistake was, in a way that would never have been possible before they became fully learned.
Here too, Shamai sent him packing for there is no such thing as giving the essence of the whole Torah in one sentence, when we still havn’t got to the bottom of it all these years. Hillel, on the other hand, played the same trick as in the other stories. He answered something that was mostly true and told him that he must learn through the Torah just to know how to apply this rule. Obviously, once he heard and liked what Hillel told him, he started learning Torah, and realized on his own how far from reality he was when starting out.