[Answered] What are some steps I can take to help improve a relationship with a friend that is quite insecure?

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Why did you remove the text? That’s not useful for us.

People appreciate accommodations but people also appreciate honesty and individualism which is more valuable to their every day issues.

You say all the things you're doing to accommodate him, but you don't say anything about why you're doing those things. Then you say he's devaluing you and calling you "too sensitive"...why are you even still talking to this guy? What benefit does he add to your life? What you say you're doing is reminiscent of how someone acts in an abusive relationship

I'd recommend being your authentic self 24/7 around him. If he can't handle that, that's on him and is not for you to fix

Get the hell out of there, the guy is a walking red flag. 🚩

I have a friendship with someone which is often like what you've described and I get similar results with him. I sometimes find that by being more formal and not 'indulging' him so much for a while, it resets things. Not totally sure why but it could be that he needs boundaries as a frame of reference to emotional stability and reality.

My honest opinion : there's no red flag, don't listen to the otger dinwit.

Stop devaluating yourself. Be proud of your accomplishments, no matter hoe small. Stop complaining. Start valuating yourself and others. Stop pointing out your foaws, value your qualities.

Nobody has fun with someone who constantly tries to play the victim and the whiNy baby. Be proud, be fierce.

This depends so much on the source of the insecurity. However, we have to adress one thing first - you shouldn't have to feel bad being around a friend. If doing these things bothers you, then don't, for your sake and theirs. Feeling bad around your friend will (as you yourself said) end your friendship over time. There has to be space for two in a relation.

For me at least, honesty is key in a real friendship. It is the most basic aspect of respect, and if something is bothering you, say so. No need to be accusatory (i.e you do this or that) and instead frame it from your own perspective, dropping it in natural conversation ("It really makes my day when....", "It really bothers me when..."). Someone who values you will pick up on these things.

You're stupid? You're trying too hard. Just be straightforward with this guys, and if he doesn't reciprocate, treat him just the same he does to you or cut him off