Ran into a kid riding Amtrak this weekend, kicking off the Spring break, and somehow he opened up about a conundrum he had with a "romantic interest" -- the boy was smitten but paralyzed! ( btw, Hi :-) Not going to share personal details but let me know how it went, or didn't!)
The details don't matter but it was like looking in a mirror for me and here's why: chasing anything -- a job you really want, a college application, or someone to reciprocate unconditional love and admiration with -- chasing anything that you think you desire always feels nerve-wracking and paralyzing! And the more you care, the bigger the stakes become!
You're anxious BECAUSE you care a lot about the outcome. This doesn't make you weak, it's a sign of your strength of character. We're only able to give a fuck in the first place if we do care. Don't stop caring; in fact acknowledging that you care deeply and that this is important to you (it doesn't matter what other people think)
You care; now as you try to make it happen, be excited for the future and curious about the outcomes -- you'll still have the butterflies in the stomach and feel sweaty and clammy but think for a second: what is the difference between "anxiety" and "EXCITEMENT"? How about "dread" and "CURIOSITY"? This is where it's easier to stop caring about what you think other people think than it is to confront what YOU think about what you think...
Pulling a lever one more time on a slot machine that's been paying out is the extreme of you feeling curiosity and excitement versus feeling dread and anxiety -- so, yes, it is possible to go too far the other way if it becomes a problem like gambling addiction but RIGHT NOW that's not where you're at, so overcoming any self-paralysis that's keeping you from "pulling the lever" is just the last but most important thing, taking the easiest possible action just to see what will happen.
People like people like you and your crush wants to be asked just like the lever wants to be pulled.
(I don't think you can go wrong to start with, "May I ask you something?" And, if yes, follow up with a compliment-share-ask like, "You always do your hair really nice! Believe it or not, I've noticed you for weeks now and have been wanting to get to know you better -- you free now or this afternoon to share a nachos at the Mexican restaurant?"
You get a reality check if she says, "No" to the first one but also it's important that you're establishing that you respect her consent -- don't be creepy! And the ask is framed where she can say no, and you can respect that and now you know, but she if she changes her mind the balls in her court to approach you and say, "how about those nachos?" -- the door's still open if it's meant to be.)
I tutor highschoolers in various academic subjects: Spanish, Algebras and Geometry, Business and SAT prep -- but getting into a good college and trying to find out what you want to do with your life is only half the challenges of life being faced when people are that age (tbh highschool academics is the EASY half)... across all domains and even as you get older, it's the same attitude and skill set (your "soft skills" they call it). Kids in 2008 are over diagnosed with anxiety as a mental health disorder, it seems, but paralyzing anxiety is real and you have to assume that people will like you (my #1 here). "Not giving a fuck" is popular nowadays but just lying to yourself that it's NOT important to you actually makes you more anxious X-) ...it's better to instead acknowledge that you care deeply about the outcome, that caring is a sign that you're a great human being and not give a flying fuck if other people judge you for it because if they do they're wrong -- then move forward by checking if you're excited and curious -- it doesn't matter how anxious or depressed you feel, take the easiest possible action that makes you feel excited and curious about the outcome.