How can I tell someone how I'm feeling without looking silly or weak?

Be confident in your feelings. Talk about them decisively and concisely. Feelings are not silly, so believe that.

You need to understand that telling someone how you feel is neither silly nor weak. The other person's perception of you isn't who you are. You should only answer your own conscience. Let not another discern who or what you are.

Ask first if they're available to talk about something serious. I personally don't think the bravery of asking for help or coming out with your feelings is weak or silly in any way, but sometimes people don't understand and that's why my advice would be to ask first if they'd be okay to listen.

In face to face encounters, taking a moment to acknowledge that we all have basic shared needs can relieve us of the notion that "I am alone." The self-critical voice of our own mind tells us we look silly or weak. Is that helping us meet basic need? That you can see for yourself, but the need to understand and to be understood is undoubtedly one of our most powerful universal needs. If we request someone to listen in that mood, such a life-affirming request can make both us and the listener feel more wonderful. If I'm shy to speak face to face, there are always trained non-judgmental listeners on this site who are happy offer emotional support, and no one can see me if I get embarrassed!

The ability to be open about emotions, in my opinion, the opposite of weak. To admit when you feel upset, nervous, happy, etc. is not an attribute many have in this age and it's quite the breath of fresh air for the people around you to understand and know what you're feeling.

Talk to someone you trust or who trusts you. Those who care about you will not judge you based on how you're feeling. Those that do aren't meant having around.

It's difficult to let people know of your feelings. It can make you feel vulnerable. If you want to share your feelings be confident. State your feelings with nonchalance.

Explain to them about how hard it was to tell them in the first place; it takes courage to expose one's feelings, after all. If your friends think that it's silly or weak to talk about how you feel, you really should reconsider who your friends are.

I don't think you can ever feel silly or weak for sharing your feelings! I think you are extremely strong for wanting to tell someone how you are feeling! You will never look stupid or weak for telling people how you will feel

Telling someone how you feel is a very big step to more things to come, or not. Telling this person should come scary at first but if the person is respectful and right for you then they will accept your feelings and exchange them for their own. If they do not feel the same try not to be bummed, instead look at this as another opportunity to find the right person that you were meant to be with all along.