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

It's always a tough situation since rejection can hurt a lot, but at the same time if you never tried at all you may never know. So I think it's worth it to pursue your desire in almost every (romantic) situation if you believe your feelings are true, because the unknown can haunt you for a much longer time

Or the pain of rejection is part of life

Sad but true, so the better equipped we are to deal with it healthier we will be

Probably the best thing I've learned in life is to disassociate actions from results. Stop wanting so much, especially things the world can't possibly promise. Do things because they feel right to you, not because you expect something out of it. In this way you will never be disappointed.

In this particular scenario, are you confessing your feelings because you want them to know, or because you want them to like you back? If it's the former, go for it and then move on with your life. If it's the latter, prepare to be miserable over and over forever.

they telling me it's cute

Exactly at this point you should take it as a "NO".

No further explanations needed.

there's a right to free speech, you can tell them how you feel. whether it makes sense is another story. for me personally, i would be flattered if somebody walks up to me and tells me that they like me.

Not enough context to give a nuanced answer. But this is the internet and you're asking strangers with no skin in the game for life advice.

So here is my piece, one or the other has to be true:

1. This is your only chance. You need to tell them or you will be forever alone.

2. There will be many more chances. If you get rejected you'll feel like crap for a while and then someone else comes along.

Nobody normal handles rejection well. Some show it less than others, but it always hurts.

Yeah that's true, I suppose I mean to face it instead of avoiding situations where it could occur

If you say anything and the other doesn't want to go farther they are likely to handle this by not having anything more to do with you. That is as soon as you say anything there are two responses: they agree and you move forward, or you never see them again!

Unfortunately every advice I (or anyone else that I've seen) can get you is right for some situations/people and wrong for others. Move too slow and they give up on you if interested, move too fast and even if they are interested they get scared off. Good luck figuring this out for your exact relationship. Even if you get it right for some relationship that doesn't mean the same thing will work for the next.

I’m generally of the opinion that it’s better to express your feelings for someone at some point than to hold back and continue spending time with them in a way that becomes a form of torture for yourself. Better to hear a no and move on than to waste time on something that won’t happen. Maybe don’t ask immediately, give yourself time to try to see if your feelings are real or a passing crush. And try to figure out if they’re even generally open to a relationship. Assuming they’re not already in a relationship with someone, is it because they are happy being single and not looking? Have they recently gotten out of a relationship and want to take time to focus on themselves? If they’re not likely to want a relationship with anyone right now, save yourself some awkwardness and try to move on. Otherwise, if it seems like an appropriate time, see what happens.

If it comes up or is obvious. Not before. You risk this person ghosting you otherwise.

My take is that you're already too invested.

Good luck. It's not an easy position to figure out.

I think it’s okay to tell someone your feelings for them, if and only if you don’t make it their responsibility to manage and regulate those feelings.

All relationships are reciprocal to a degree. Liking someone is normal, if they don’t reciprocate those feelings that’s okay, doesn’t mean anything has to change. If you respect them as a person and don’t just see them as someone to fill a role in your life then you should be able to sublimate romantic feelings into a healthy plutonic feelings.

Don’t force anything, pay attention to expressed boundaries and learn to differentiate for yourself when you’re giving too much.

Okay here’s an alternative route:

Rather than trying to express this with words, do it through meaningful action. Go out of your way to spend time with this person. Suggest things you can do together even if it’s just going out for coffee or shopping or whatever. When they open up and share, listen in earnest and express empathy. This will allow your feelings to show themselves organically without you having to concoct some awkward-ass monologue about it. This will also provide you with nonverbal feedback about how they feel, and you can proceed accordingly.

Took me decades to figure this out myself btw.