Aw hunni. I feel you. If he’s shy that might mean he’s ok with comfortable silence so sometimes just not talking can be good. But try and talk about anything. Make a list of thinks that are relevant to both of you that are good conversation topics. If you can’t memorize it that’s fine you can always check your phone. If you can’t think of any good things to talk about in the moment just look around and comment about things. Like how cute some girls dress is or whatever. Or how so and so seems to be cuddling up to so and so and how cute of a couple they would be. Or how the school decided to change a thing in the halls. I don’t know. Random shit and gossip. Talk about a funny thing that happened in a class. Or something someone said. Oh and important. Don’t talk about you all the time. Ask him questions too. Abouthow his day was and how he’s handling certain classes. Grades are always good topics. Teachers too.
And that’s my experience hope that helps!

I’m pretty shy and usually okay with silence. I think if you just ask a few questions about him and you are genuinely interested in a response he’ll notice your interest and maybe the conversation can unfold. I feel like everytime I try to plan a conversation it never works

Ask some questions! Ask him what his favorite type of music is, favorite movie, favorite show, favorite book, if he has any pets, and then maybe a conversation will spring from that! Good luck op.

Just hang out with him, he'll appreciate your company.

Yes good luck let us know how it goes

Aw thank you guys for the great advice! The thing is is that he gives really straightfoward responses so it's hard for me to kind of play off of it.

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