damn... sounds like an annoying boyfriend... an annoying everything... :/
people like that get on my nerves...
Next time he says it, tell him to do something productive then. Do something with your life, do something useful.
These type of people sometimes don't need reassurance or to be praised and such as you're doing replying with "no you're not"... and "i love you, you're amazing" and such.. etc. etc... What they need is to be told "yes you're right, you're pathetic so go do something productive with your life." ... and if i were you i would have left him already... and if he really wanted to be with you he's try to get you back and to change his lame personality.
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Confidence is all about how you present yourself to others. It's an illusion. Deep down we're all insecure, but not everyone whines about them to the people around us. Maybe you could encourage him to find a better emotional outlet.
I'd recommend joining an online community with other like minded people who can "get" him. That should provide some of the emotional reassurance he needs.
Right now you're feeding him with all of the 'typical' responses which actually frustrates him. Misery loves company and an always-positive response to a downer comment feels insincere. Be honest & true about what you're thinking.
You can either break up or have a serious talk with him. I recommend talking first. If it doesn't stop and it bothers you too much just break up. He seems depressed, maybe tell him to see a professional?
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The normal female red light that flashes "This guy has no confidence. Abort. ABORT!" didn't kick on.
You should get that checked out.Be blunt and honest. 'the only reason you are pathetic is because you are making yourself appear so. man the fuck up'
If he says you deserve better then you do
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