Is it okay to express your feelings for someone even if you don't think they reciprocate

Yeah, love is only for people you're in a relationship with and those you aren't seeking a relationship with. You can say you love your best friend, but if you start dating them, while the intensity of your feelings for each other may increase, the relationship is back to an early stage, just in a new track. You haven't built that track up enough for that word to feel safe and comfortable.

When you're pining over a friend you're partly thinking of them in the romantic relationship track. This means professing love doesn't just come off as "I care deeply for you" or "I'm interested in romance", it comes off as "we're getting pretty serious in my head, you should get in on it."

In general mismatched feelings are deeply uncomfortable and the more mismatched they are the less comfortable.

People do not appreciate having the love of people they don't feel the same towards. It's awkward and it feels like an obligation or expectation. It makes you overanalyze every interaction and want to pull back.

"Hey, I've been developing some feelings for you and was wondering if you felt the same way?" - normal, low expectation, allows rejection or acceptance without pressure

"I love you (and want a romantic relationship)" - intense and uncomfortable, high expectation, high pressure, may leave them wondering if you'll take no for an answer

I realized that if someone was young enough and expressed their interest I'd be weirded out by that

Shit an actual cautionary tale that's applicable to my situation. Most people assume I'm trying to gain a romantic relationship.

If someone else asks I guess I should play it off? I assume if they figured out through third party it would be weird

So flirting. Quite a bit people recommend I go the flirting route which seems perfectly acceptable. I just suck at flirting and I still communicate in a stiff and direct way

Good luck.