Well first of all you cannot stop someone else doing something. All you can do is control what you do.
You also cannot control how they react.
My impression (and I'm only hearing your viewpoint, of course) is that your friend is trying very hard to do something they're not good at (develop friendships). This may be one of several things :
- They're just trying too hard and don't understand this
- They're possibly not aware of the need to listen (it's an art people do not practice enough)
- You may not be good at listening. :-)
- They could be romantically interested in you (not enough info to do more than speculate).
- They could be a very needy personality which can be hard to deal with.
A few comments :
I feel like he is trying to make conversation just for the sake of talking
People do need to talk. People who are lonely or insecure often need to talk more than most and are often the least equipped to do it well.
, and very rarely about anything I'm actually interested about.
This points to a weakness in your mindset.
The way to make friends is to force yourself to take an interest (whether it's real or not) in what the other person regards as important.
This is the art of listening and feeding back to them that you accept that.
I am quite certain I bore the pants of some of my oldest and dearest friends with my interests, but I am equally certain that they listen and laugh with me because I do the same for them.
You may not fully grasp this mechanism. Give it some thought.
All he does is ask me never-ending questions and sometimes it becomes both annoying and exhausting.
Someone who has minimal friend-making skills would probably consider asking you questions as the best way to expand your friendship. Them asking questions is them trying to demonstrate an interest in you.
I have tried to hint that I am not interested by responding with one-word messages or short phrases, or, sometimes, by not responding whatsoever.
Have you tried asking questions back ?
For example :
I'm into football. What about yourself - are you interested in sports at all ?
In a way you are expecting them to do all the work in a conversation.
I have a friend very active and interested in a particular sport which I have absolutely no personal interest in whatsoever. Nonetheless I listen and discuss this with him when I see him. From what you've said your reaction would be to try and turn off the conversation because it doesn't interest you - that's not how friends should interact.
He's still pushing conversation, even it feels like I'm being interrogated (he isn't great at keeping an engaging conversation).
It takes two to tango !
Are you making engaging conversation from his point of view ?
He is also very emotionally sensitive: a while ago, I requested that he give me a bit of space because I was going through a hard time (true, not an excuse). He then went to a mutual friend and started worrying about if I hated him.
The picture you paint is of someone reaching out to you and being rejected by you in a relatively cold way.
The other person may or may not be being oversensitive (I can't properly evaluate that based on what you said alone), but if you said that to them they may simply have picked up (quite correctly it seems to me) that you don't want to be friendly to them and are trying to discourage them.
So you may be the person with the inappropriate viewpoint here. The other person seems to understand exactly the message you're sending - you're sending "get lost", BTW.
How do I stop him without hurting his feelings
Bit late for that. You've clearly already done that.
You should probably give some thought to whether you want to try and heal the rift (which means properly engaging them and helping them have a conversation) or actually want to drive them away, in which case keep doing what you're doing.