How can I help him feel comfortable/confident enough to make a move?

I can tell he likes me and I try to encourage him and boost his confidence as best I can but he just seems so scared to make any kind of a big move! He gets nervous around me which I think is adorable... but I want him to feel comfortable too. Like I said, I try my best to let him know I'm into him, but I don't know, maybe I'm not sending the right signals or am doing something wrong? Last time he asked me out, I could tell he was thinking about it for awhile and then it was like he just spit it out really fast (like ripping a bandaid or something) and seemed SO relieved when I said yes.

Another thing is he'll make a suggestion when we're together in public, like going somewhere kind of romantic alone after, and I'll say "yeah, sure!" but I guess I'm not convincing enough or something because when the time comes to actually go, he'll hesitate and then just act like he never suggested we go up to the rooftop or whatever it was. I figure maybe he's changed his mind so I'll wait for him to take initiative (which, he didn't) but then he acts kinda hurt/defeated... I don't get it? Any insight would be appreciated.

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  • he mgiht want more reassurance because he is kind of insecure. did you call him on it every time he hesistated?

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  • This guy seems super shy or awkward.

    Maybe try complimenting him on things... flirt with him a little bit more that kind of thing to suggest your more interested.

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