Replying to Pushing a relationship

Made this in ask a girl cult but figured no one would look at it.  Advice will be thanked

I've been getting fed up with being single and I've found someone that I like but I feel like it won't work.  Would you rather be told that you don't think it will work or just let it go?

Also, I've had relationships with people and I really don't feel like I connect with them.  So far I haven't had one girl that truely understood how much skiing meant to me.  And I haven't found someone that I can really connect with about skiing.  Is it best to just wait it out and hope that I find someone skiing or something?