There’s this girl that I’ve had a major crush on for a really long time, and that I’ve never worked up the guts to ask out. For a while I couldn’t do anything about it because she had a boyfriend, and other times I couldn’t do anything because I was just too chicken. Actually, that seems to be my problem with almost anyone I’ve ever wanted to ask out: I just am so risk-averse that I can’t seem to take that step and spit out that stupid little question. The worst thing about it is, I’ll become friends with these girls and then that brings about a whole new obstacle. Do I risk a friendship by telling my secret about having a crush on this girl, or is it better to just forget about dating altogether and have a lot of friends?
I know how you feel. In fact, I’ve been through this same situation too many times to count. After much careful thought and thoughtful planning, I believe I have come up with the ideal solution to your problem.
Here’s the plan: I call it the “Self Improvement Survey,” and it allows you to be perfectly ambiguous and hypothetical in your probing of a subject (the potential date) as to whether or not you will get the desired response. The first step is to make up a bunch of questionnaires asking a couple of simple questions: (1) What would you say if I asked you out? and (2) Why not? (This one could have a list of multiple-choice answers such as (a) You have a boyfriend (b) You don’t like me (c) You like me, but as a friend (the killer) and (d) other.) You should also provide a space for comments, and encourage them to provide you with a few changes you could make to your personality/appearance in order to make you more desirable. Then proceed to bring this survey to any girl that you’ve ever thought about asking out, but were unable to due to your wussy-ass nature. This should allow you to gather any information you may need before popping the question (including what the answer will be), and hopefully you will find at least one that doesn’t add a comment like “You’re an ugly dork and too hopeless to improve upon, so just give it up, Creep!” Hopefully.