So, I can't super relate to this, but only because I'm unhealthy in the other direction. I'll tell anyone I love them pretty much at any time. The only time I have this issue is when I don't love someone who loves me. I think it would be mean to say it back because I don't want to give them false hope or the wrong idea.
I know this isn't the case for you though, so it really sucks that you have a hang up about it. It's awesome that the dude you're with is so supportive and understanding, but you're right, eventually people do start needing those reassurances.
For now, I think you should keep those lines of communication open. Like, not a conversation you had several months ago, but something that you keep up with. If he sees that it's something you're actively working on, he'll be more inclined to stick with it. You have to show people improvements, no matter how small. Any step in the right direction is going to be progress, and someone who is supportive only wants to see progress in some form.
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