1. There’s really no sure way to just let it happen. I know exactly the way you feel, and it took me 7 months of dating my boyfriend to open up that part of me again. But it did happen. You just have to let him help you get over it. This guy is very nice to you. I’m sure if you told him your story, he’ll understand and work with you to help you move on from it.
2. There could be a couple reasons. One, he doesn’t know where you guys stand. He wants to be together, it’s quite obvious from what he does with you, but he might be waiting for you to make a move and isn’t seeing it happen. So he doesn’t know what to do, and sometimes he decides it’s best to stop this behavior, but then finds himself back next to you again. The other reason is that he’s hiding something. He likes you a lot and likes to be around you, but maybe he’s also in a committed relationship and hasn’t yet decided which one he desires more. So he tries to justify it by not hanging out “as much.” I would try to talk about it with him to be sure what exactly is going on, though.
3. Yes. Heartbreak comes from love, experience, feelings. It doesn’t come from how many dates you’ve been on or how you labeled yourselves.