Shy unpopular guy to date a outgoing popular girl?

So if there is a shy guy who's very mellow, not easy to talk too because he has not much to say since he's not outgoing with girls, or much less anybody, and he is not popular at all, he is kind of standoffish, it is popular to he is able to date a girl who is very popular with a group of friends, almost to the point where she is clicky with her group, and may be standoffish to other people, not necessarily the shy guy. Or are those two completely different and even a first date who not work at all. ?
Shy unpopular guy to date a outgoing popular girl?
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