Should I just ask him out?

Illustration/Uday Mohite

I like a guy from college who is a year older than me. He is incredibly shy so whenever we meet each other, he smiles but never says anything to me. I am convinced he likes me but don't know if I should ask him out because he may get too anxious to have a conversation. My friends tell me he has never been in a relationship because he struggles with social situations, but that is why I want to try and take the lead and encourage him to come out of his shell if possible. Is this a bad idea? I don't want to ruin a potentially good thing by coming across as too pushy. At the same time, if I don't do anything, I'm pretty sure he won't say a word.
If you want to take the first step, you should. If he can't handle social anxiety, you can try taking it as slow as possible, provided you understand that this cannot work if you're the only one doing the heavy lifting. It's also possible that you misconstrue his friendliness, so figuring out if he is interested ought to be the first thing you do before planning how to navigate this situation going forward. Try opening a conversation with him and starting with small talk. If that doesn't happen, or is too difficult to pull off, you may have to temper your enthusiasm about the possibility of a relationship.

Is it normal to be in love with someone who is still clearly in love with her ex? My girlfriend is with me, and wants to be with me, but can't get her ex out of her mind and this just causes a lot of depression that I can't manage. Should I assume she is with me only because she can't be with him?
Why assume when you can ask her directly? If she isn't as committed to this relationship as you are, and cannot put her past behind, your exasperation may soon tip over into resentment.

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