Q21: What if I never see him again?

From "Trying to Go Out With a Bang" via Blog Comment:

Dear Beaver, I've had a crush on this guy for nearly a year now, but have never been able to work up the courage to actually ask him out. Thing is, the situation is changing--and I'll probably never see him again. I realize that the smart thing to do in this case is to get over him, but like I said, I've had a crush on him for a long time, so that's sort of hard to do. What should I do? How do I get over him?
- Trying to Go Out With a Bang

The short answer to your question is this: there are two types of regret (regret for having done something, and regret for not having done something), and you have to decide which of those regrets will hurt more.  In my opinion, the latter regret is more painful.  Also, I tend to think that in matters of love, we should risk rather than restrain.  

But is a crush on the same level as love?  No.  (This is the long answer.) There are plenty of risks to pursuing this crush in the short term—do you actually know who this person is?  I personally have discovered multiple times that my crush is not the person I previously imagined her to be.  We tend to create an image of our crush, rather than see the person as s/he truly is.  In other words, be a little bit skeptical of your own tendency to place another person on a pedestal (we all do it).

On the other hand, you can learn a lot by following your desires and stumbling along the way (the stumbling is inevitable).  Even if pursuing your crush turns out to be a mistake, as long as you are open to the lessons such a mistake offers, it won't be a total loss.

Another possibility: picture someone you truly admire, and ask yourself what that person would do if s/he was in your position.

In the end, you have to decide for yourself.  Terrifying, isn't it?  Truly listen to yourself, striving to be honest, and then make the best possible choice.  Take some time alone to think.

(From another staffer): If all you want is some action, then go for it. The easiest way (as bad as it sounds) is probably to get drunk, confess your affections, and go at it. However, you do have to think about what would happen in the long run. If this crush is a really good friend of yours, then this confess-your-feelings thing might make your whole relationship a bit awkward. True, you'd never see him again, but when you do keep in touch, it might be painful. And who knows? You might see him again, be able to laugh about a crush that you once had, and gain a deeper relationship. Also, gauge the signals: how does he feel about you? Would you be willing to risk what you've got now for a fling? Would it be incredibly awkward after that fling? Would you feel immensely fulfilled, or just want something more that you can't have? Either way, it'll probably feel empty. Long story short: If you're attracted to each other, and relatively comfortable with each other, then go for it. If not, just keep in touch over the years.

As usual, be safe, and have a great summer!

[Note]: If this didn't answer your question, or if you want more details, feel free to post/email/ask again!