22M

I have Low Self-Esteem and have certain mental conditions that make me highly anxious/tense and hypersensitive overall (physical, sensory etc...), including social life and especially relating to romantic involvement.

In middle school I was publicly humiliated in front of plotting and anticipating individuals. With a "friend" and past crushes being involved. Being a vulnerable and clueless individual was probably the primary reason for being targeted.

That was my first and last time asking someone out. I have always had poor social skills, improperly socially calibrated and the like.

My social life at the moment is quite hermit like. I minimally talk to anyone. I tend to self sabotage in the forms of being avoidant with making little eye contact, being monosyllabic etc... Sometimes I get over it and speak for longer periods. I believe I speak to the opposite sex almost as easily compared to others.

However, when I notice interested glances from ladies. Get into decent or even playful conversations with them. I become very hesitant, being afraid of taking it any further.

Primarily because to my embarrassment currently still relying on external income, living under parents, not being properly domesticated and investing more into entertainment and multi media systems over appropriate furniture and decor... unappealing wardrobe and clothing maintenance. Only thing I could say I would be comfortable with would be hygienic upkeep thanks to some OCD traits. From a glance I would come off as a slouch, lazy, incompetent, immature, irresponsible and careless. Much of it being true, I feel like a lot of priorities/prerequisites need to be met before advancing pretty much any aspect I wish to improve in my life.

Any constructive feedback on how I should approach this, techniques to get myself into the right mindset/attitude or whatever else?