So you want to try create the right moments for deeper conversation, I think that would be more likely away from his mates? I don’t know them so just guessing.

With that in mind, maybe Google around for anything interesting or different happening in the area. A gardening or book faire, wine or coffee festival, anything relaxed. Then ask him if he wants to go. Ideally something quiet that has some walking around?

That might create helpful conditions.

Tricky, but you could take the approach of just putting it on the table:

"Hey, I have a weird random question… " And then ask if he thinks there is life elsewhere in the universe or what he thinks is going on with flat earthers or whatever. It isn’t bad to be a bit random in timing.

In terms of timing specifics though, you don’t want to do it in the middle of some other discussion, so you normally wait for a quiet moment or a lull in the current conversation. Typically depends on what’s going on. I find something like building puzzles together is great for this, because you’ve both got something to do but it’s not so intense as to block easy conversation that just meanders a bit. Just an example though.

When you are together, what are you normally doing? Long drives are easier to find ok moments, studying in the library or in the middle of a dentist appointment less so

You could try asking some deep questions, see what comes out of that.

Snuggling? Uh, that’s a hard no. I can’t imagine that. I’d be extremely uncomfortable.

Hugging? Yup, lots of hugging in my friends and family.

I don’t wish for more physical affection among males, seems good as is.

I had the impression that people running for office in Mexico were being assassinated a lot, if she is real force for good then I hope she’s safe

People down voting have no sense of humor.

Take it as a meditation challenge, just be alone and quiet with nothing but your thoughts.