I just feel so stupid

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Hey, don't feel stupid. My advice to you would be to really listen and just to ask questions about him when there is a puase in a conversation. When he asks you a question reply and possibly ask the same question back. It's a way of knowing when questions can be asked. Don't feel shy, if you have a question and the opportunity to ask it. I would tell you to go with it. Try to make the conversations even between your experiences and his. Try to turn things around so he can answer them too. If that makes sense. I hope this helps you a little bit.