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There are two big issues with this whole thing...
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These don't sound like issues, just endings that you're not happy with. You're asking us, should you let these sleeping dogs lie or change their outcomes so that Caleb falls in love with you and/or you find the random guy to live happily every after? Sounds a little bit like the Lady or the Tiger...
Why don't you use these two issues/endings to examine your own impulses? Obviously, you're not happy with the sex from random, so it would probably take a good, deep emotional connection to make the sex !awesome! Or a lot of communication. Do you feel like pursuing an emotional connection with a guy where you already know what the sex is like, you were not impressed, and it would take a lot of moxie and charm to own up to the fact that you don't remember his name?
Two, sex is obviously important to you. You enjoy it and have definately opinions about how it should go down (see: comments of size, etc.) Are you sure a virgin is a great match with you at this point in your life? There is absolutely nothing wrong with having sex, whether you want to get down in a relationship or a one night stand. Caleb is definately going to feel very differently about sex and all the latter bases that come before a home run. He might know nothing about what happened with you that night, but you and him might not match up when it comes to your own beliefs about sex before marriage - and these opinions are a huge part of relationship and differing opinions can be a huge stress on a relationship.
Last, if you're nervous about talking to guys that you like, and you find comfort in getting drunk, I recommend finding a balance to your two selves and letting Caleb and random be.