Making a highly sensitive but insecure man fall in love?

So I have this friends with benefits who is the most emotional and sensetive man I have ever met. He is wonderful! He has been burnt real bad a couple of times before so his confidence is quite low and has some trust issues. I try telling him I REALLY like him but he doesn't really trust me. The thing is, I am not used to interact with men this sensitive and with such a high E. Q that I was wondering if anyone had any advice... It's very well outside my experience and I don't want to hurt him by being to brute or something like that. All advice is greatly appreciated!
Making a highly sensitive but insecure man fall in love?
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