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This may be not great advice but try thinking of a few questions you’d want to ask him if there is ever a lull in the convo. It could be surface level stuff or more personal stuff that you know about him from his profile or through messaging.
If you have a close friend, call them up and ask to kinda simulate a normal date convo with you. Try and work in some banter or flirting if you think that’ll go well too on your date.
I’m also really shy but I realized after a while that if you always stay shy you’ll never get to show the person who you’re interested in who you really are. Be bold! Be funny! Be mysterious! But above all be yourself! It’ll be hard at first but hopefully there’s chemistry there + reciprocation on his end. Good luck!
I suggest instead of dinner dates (i know this isn’t necessarily an answer that fits your question but it will help down the road) go to the arcade, bowling, events, places where you guys aren’t just staring at each other and interviewing yourselves. That will keep the pressure off and introduce an element of fun without the awkward moments. You’ll definitely find something interesting to say when the pressure is off while you two do fun things together. Just a thought for next time! good luck with everything