Should I just tell him how I feel?

Illustration/Uday Mohite

My friends have been giving me all kinds of advice about a guy I have a serious crush on. He is a year or so older and we have been in the same college for over two years. We know each other, and he is single, but I don't think he likes me or thinks of me with any intentions of getting into a relationship. I have given him a few hints, but I don't think he gets them because we have never had a serious conversation, so he probably thinks I am just being flirtatious. My friends think I should drop it and give him time to develop feelings for me, but how is he supposed to just do that? They say if he doesn't express interest, I can't force him to like me. I believe the opposite makes more sense. If I tell him how I feel directly, he will have no choice but to start looking at me differently. I don't know if this will backfire though, which is why I am not saying or doing anything. Should I listen to my friends and just wait?
What stops you from asking him out and initiating a real conversation? You know each other, and if he isn't interested in getting to know you better, that's already some kind of answer. The state of limbo makes no sense after a point because if he hasn't said anything to you yet, he's obviously not thinking along the same lines as you are. Ask him out and take it from there.

There are some things my boyfriend does that make me worry about his character. There is something shady about him, which I don't pay attention to because things are great between us. I don't know if this is a smart thing to do. Should I confront him?
If you aren't comfortable about something, you should always speak up irrespective of whether it involves your relationship directly. If you believe something about him his shady, always trust your instinct.

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