>>33908352
It's okay to have silences. If it's on a voice call, count to 20 in your head when the silence begins. More often than not, they'll usually fill it with something.
It's also okay to just say how you feel sometimes. All of the stuff you said here for example, is okay to say. Worst thing you could get out of him is boredom. Anger, sadness, happiness, out of all the possible emotional reactions he could have to something you said, the worst will always be apathy.
So start by saying stuff like my mind is going blank if that's what it's doing. Most conversations are based around specific sets of ideas. A sentence will have specific things you can elicit and pathways you can follow. For example let's say I said "oh my dog is going to the vet today because he hasn't been feeling well".
This sentence has a bunch of things you can ask me a question about. Dog. Vet. Today. He. Feeling well.
You could ask about whether he likes dogs more than cats. Ask about whether the vet is close or further away. Ask about whether he's going in the afternoon or the morning today. Ask about whether it's harder having a boy dog than a girl dog. Ask why the dog's not feeling well.
Recognize those data points. Have a set of canned questions. Rudyard Kipling's got those 5 critical thinking questions. Who. What. Where. When. Why and How. Pick a data point, pick a critical question, follow that path for a bit. In between things, pepper in your own stories. You can find parallels in your own lived experience that might resonate with what the other person is saying anon. Going back to the dog sentence...
"Omg you must be so SAD. I remember being really sad when my [insert pet, sibling, parent, etc. here] was feeling bad". People grow closer to you when they feel like you resonate with them.