I have been hanging out recently with someone I have known for a long time. We went to school together but we were both the kind of people that wouldn’t start a conversation unless someone started it with us so we never really became good friends. After school however things have changed and now we’ve started hanging out. I have strong feelings, and the outings generally go really well. But every single time it’s over and I drop her off I just get this miserable feeling on my shoulders. It’s not something I am used to with people. Is this a bad sign? What does it mean?
Hi there. To me, it sounds like it could be any number of things. You could simply be worried that the friendship will fall apart, or you could just like her.
If you like her, and that's what I think is happening here, and you guys are close and have known each other for a bit, maybe think of asking her out. If she was shy before, she will most likely not approach the topic of dating first! You're going to need to act on the feelings this time if you don't want to lose her.
I'm not saying that telling her you have feelings for her or asking her out will guarantee a yes, but that's what will get you your answer. All of this of course depends on how often you see each other, if she has any other friends and if she feels for you the same way generally without outside influences.
I would explore how you feel, and act on that. Once you know if you like her as more than a friend, or if you're just afraid you may lose the friendship for any other reason, it will be easier to see what it is you really do need to do. All the best etc.