Play drinking games. Or just sit around and get plain old drunk with each other.
Alcohol: Bringing people together since forever.

>>17166152
Personally I'm not much of a drinker, but sure, I could give that a shot! (ba dum tss.)

>>17166123
i have no advice for you that doesnt involve some variety of intoxication, but i kek'd audibly at your image. so thanks for that.

>>17166169
No problem, anon; glad to know I'm not the only one that finds these feathery little bastards hilarious.

Maybe he actually just isn't that talkative. If this were true would he bore you?

>>17166123

You might be over thinking it. Just ask him.

Or if you don't want to take that approach, find situations where your questions won't feel out of place or forced.

If you're watching a movie: "What's your favorite movie of all time?"

Something to that effect.

>>17166324
Not at all! I'm comfortable how we are, we spend time together and communicate really well.

It's not really a problem that he's so private, but rather I'd just like to feel closer and know him better. But after a while, asking him direct questions about himself starts to feel interrogative.

>>17166123
How long have you been together?

>>17166333
Yeah, I think this is my issue, with questions feeling too forced; I'll just have to watch out for more appropriate times to pry a little more about him. Thank you for the advice, anon!

>>17166347
Not terribly long, about 5 and a half months! Still lots of time to get to know one another, but he's the first person I've dated to be so reserved, so I try to tread carefully and don't want to accidentally overstep any boundaries.

>>17166353
I think he'll open up more in time.

>>17166362
Hopefully so! He's opened up drastically (going on what he's told me) in the time we have been together, so I just need to be patient.