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I had no idea...
So, my ex told me tonight that the reason he has never had a relationship where he sees it lasting is because I broke his heart 5 years ago and he never wants to feel that way again. We were each others' first long term relationship and firsts in a few other ways to put it nicely. We were together for almost 2 years. He likes someone now, and is afraid of getting hurt. I feel kind of irresponsible that all this time (we started to talk again about 7 months ago) that i did not know or think about my impact on him.

I broke his heart, and all I could do tonight was grab him, hug him, and tell him he is amazing enough to deserve to be loved by this new guy. I want him to believe that. How else can I get him to be confident enough to go for it? How can I help his broken heart?

Yeah I know, it couldn't be more complicated.
its great that your both back as freinds and you sound that you really care about his future - just be there for him and encourage him to go for this new guy he likes - just like your doing really,, a breakup is very hard on the person who didnt want to end it so i can see how upset he must have been and why he doesnt want to be hurt again - tell him you'll be there for him no matter how it turns out if your commited to having a freindship with him - its always nice to fall back on a comforting shoulder
Well, there isn't much more you could do to give him confidence because too much advice can be bad. Hug him and support him and be his friend....I think this would help him.
To be honest, I think he has to find his own happiness. Getting the most out of a relationship often means letting go of fear and that's not something you can do for him.
Thanks for the feed back. I kind of feel I know what I should do and how to go about it. I guess this really is the first time in my life I actually considered the idea I impact people. I have always had low self-esteem but hid the fact rather well. When he told me I was the measure he used on all other relationships I did not take it seriously. I never thought I could be important to someone. That is why I am single now I bet. But I want to take this opportunity to be there for him and learn to like myself too.
It's sad that he's like that. He sounds like he could make a great boyfriend.

I used to think like that after getting my heart broken into 180,000 pieces.

But have come to realize that it'll happen again, and it's not worth judging every potential boyfriend over your last ex(s). It's not fair to them, it's bringing in old baggage.

It's better to start fresh and over with each guy (including Recycled lol lol lol), and do your best in the relationship, With a few slight Modifications so to speak so you don't end up winding up in the same situation.

How else can I get him to be confident enough to go for it? How can I help his broken heart?
To answer your question: You can always try my method.
Say the same thing or same message (in different ways) over and over and over and over and over and over and over and over and over again until he gets it lol.

Oh and small tip you can tell your ex boyfriend: When he meets a potential boyfriend, test him out. Run the potential boyfriend (without the potential boyfriend's knowledge) through a series of tests to test his loyalty, judgment, honesty, etc. That will tell your ex if he can really trust the potential boyfriend or not. If he's got a keeper or not lol.

Just a couple examples of slight modifications lol.

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