How to hangout with a shy guy and make things not awkward?

This guy asked me to hangout just us this weekend, the thing is, when we hangout its usually in a small group which makes things better. were both sort of awkward, but just when we are talking, just because we like eachother and we have trouble keeping conversation. And the last time we hungout we both had some drinks which made us waaay more outgoing. so I guess my question is how do I make things less awkward? and how do I keep conversation without it getting boring. I am a pretty confident and outgoing person around anyone but him for some reason. so please help!!!


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  • Just have a couple of drinks to loosen each other up then talk about mutual interests


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