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Find out what he's great at or really passionate about and ask him to do it with you.
That way, he can earn his confidence back because someone appreciates him for what he is capable of — and he doesn't have to prove a lot to you. Introduce him to your circle of friends so he doesn't go questioning the people around you and what your relation with them is.
If you are currently dating a guy who has a history with an unfaithful partner, you are therefore dealing with someone who may have some serious trust issues.
Basically, that he's arrived to save me from my terrible, sad, fat life.
I love Netflix and whatever as much as the next girl, sure -- but I also love art galleries and movie theaters and poetry readings!
And yes, I even enjoy going out for a good meal if you can manage not to make a big deal out of it.
Although his personal ego is his own issue, there are some things that you can help in improving his self-worth.
Make him realize that the fault doesn't lie with him.