Quote Originally Posted by Astral Avenger View Post
Situation in a nutshell:
I like a girl who I've been (cross country) skiing with for the past 5-6 years. Right now we are both (technically) seniors in high school, but taking all our classes through two local colleges through a state sponsored program (I go to one college, she is going to another) and are effectively freshmen at the two schools. We've been friends since we originally joined the high school team back in 7th grade. Next year, she is going to switch to the college I'm currently in, and I'm either going to stay in the college or go to UW Madison, haven't decided yet. We're both going to be gone for about two months this summer on various trips too, I'm going on a 45 day canoe trip to far northern canada, she is going on a ~40 day backpacking trip in Utah/Colorado. Of course, all that matters is that I just have to psych myself up enough to ask her out.

So, any tricks for convincing yourself that its better to just ask and (hopefully not) get rejected than to just go on wondering?
Well by actually asking her out the only thing you really risk is a hit to your ego, which is not really a biggie. On the other hand you stand to gain a date with a lady you seem to dig. That is a pretty good ratio of win-to-lose!

Also not doing it is in the long run likely to be a bigger ego-bruising what with the 'what ifs' and 'woulda shoulda coulda' style thoughts that can take over when you have the glasses of hindsight on.