My crush likes me.. but its awkward. What do I do?

background: this guy i had an on and off crush on for 3? years now recently just texted me 2 weeks ago. when he did, i completely forgot who he was lol. the last time i talked to him was in march? he has a twin sister whos my friend, which makes matters both worse and better. the sister and another friend asked him if he liked me, and he said yes. since then, he has been texting me daily, (although very very dry convos), facetiming with another friend, and we hung out once with him, his sister, our mutual friend, and me. that mutual friend is a girl who has also been texting him advice and stuff around me LOL.

i know he likes me, but it's extremely awkward. when we hung out, we did the sweatshirt and scrunchie exchange and he did the counting shoulders thing.. but our convo was really dry and we were both obviously nervous, yet being with other people helped relieve the stress. he's planning on asking me out before Christmas, but i'm not sure how it's going to work. we are both shy people and even just the thought of being alone with him scares me. any tips on flirting? holding convo and getting closer? any advice on this situation?
My crush likes me.. but its awkward. What do I do?
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