Do guys psych themselves out over making the first move and how long does it take you to get up the courage?

I'm asking for guys who don't consider themselves super confident with women and girls who have dated guys like that. I've been seeing a guy for over a month (date count: 6) and while we have a great time on every date and we haven't gone more than a day without texting, he still hasn't kissed me or even held my hand. He warned me he wanted to take things slow since his last couple experiences didn't go so well, and he shows interest in me through conversation and body language, as well as trying to extend the time we spend together, but at the end of every date I get a hug, asked out for another date and then another hug. The hugs have at least gone from awkward, short one-armed to two arms and more than 5 seconds :P This guy is very different from all of the guys I've dated in the past, in a good way, but also in that he's the first that hasn't tried to make a move on the first date (or 6th...). I've also wanted to make the first move but I've chickened out myself. Could I be giving him signs of disinterest? Or is he really that shy? What should I do?
Do guys psych themselves out over making the first move and how long does it take you to get up the courage?
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