Anyone have experience dating this type of person?

I haven't dated this person, but I have BEEN this person, and sadly these relationships usually don't last for that reason.

Have you actually tried talking to him and trying to show him that he can trust you?

 

I'm that type of person. Spend more time together, let them get more comfortable with you. Talk a lot, share your secrets with them, build trust and comfort slowly. Work on pair bonding.

 

Gaining trust takes time. Be patient & let them warm up to you. Do things they enjoy. Talk about things they like & what they don't like; don't be judgemental. Carefully listen to what they say. Show them how you are worthy of gaining their trust by giving them consistency. Do not make the mistake of trying to pry them open & later on decide you are tired of them. They could be opening up to you but they won't show it.
Maybe give them something that has high sentimental value to them. Something meaningful.

 

This is the best thing to do.

 

My current girlfriend was like this. We met almost a year ago and within the first week it was clear to me that she wasn't over her ex because she would constantly talk about it and she was extremely hurt by their breakup. I didn't want to mess with it so we stopped talking but a few months later we began talking again, slowly but surely. We became best friends and almost got close to dating again, but she told me she still wasn't ready and didn't want to commit if she didn't feel like she was 100% back. We remained best friends but went our separate ways dating-wise and saw other people, etc. When something didn't work out we were by each others side and always hanging out, strictly platonically.

Almost half a year went by before, this time super slowly, we became more intimate with each other. I let her initiate everything and we went at her pace, and since we were best friends it was easy to fall into place and we 100% trust each other. Now we're dating and it feels great, because it reassures me we're both at 100% and I finally know she's over everything in her past and can focus on us now.

Basically with someone like that it takes A LOT of time and trust and sticking with them. You better make sure they're worth it and you better be in it for the long haul!

 

yes i have met this person and i have learned to drop them as soon as i see or meet them. we all have baggage but if you have so many walls up to protect you from being hurt, then there is no way for the other partner to win in that situation. you will only be frustrating yourself because everything you do will be a test to the other person that "yep, i was right, he's just like the rest of em." some people like this even play games to see how dedicated you are to trying to break down their walls. i do not have the time or the mental energy to dedicate to trying to deal with someone else's walls and baggage. until they decide to tear down their own walls, you'll never get their heart. you'll only be in this constant state of trying to prove your worthiness to them and that you're not like the others. if they are unwilling to budge, just drop them and move on to someone who is emotionally and spiritually ready for love. if not, you'll waste your time with these people.