Due to many deep personal issues, I refrained from dating for all of my teens and honestly regret it a little but not in a major way. Like a slow poison of sorts working its way and festering in my mind to the point where I feel I can't ignore it anymore. I will be 22 in a few months, when I'm 22 I actually want to go on a date. The biggest reason is that I don't want to say " when I get my life in order" - while I fundamentally believe that getting your life in order is key for a long term relationship I have slowly come to realize that my life is never going to be in order for a very long time. I always imagined naively that I would start dating when I've settled into a real career and things resemble some sort of normalcy. I realize my life is so f**ked up this will never quite happen. I've been self improving for many many years and it's been a slow & steady curve that goes sideways on occasions. I don't want to be 25 year old me still saying- "when my life get's better" , because 25 year old me will regret as to why 22 year old didn't start and then the mountain becomes even bigger in my head. I know that whatever fear I have is irrational, girls are not THAT big of a deal. They can be people with arguably even more flaws and insecurities than me and tbh most of them are kinda overrated/basic where I live in North America especially. I want to focus in the real world and ask someone out but even the thought of that makes me tense, I don't wanna "whore myself out" on online apps because quite frankly that's a rigged game where if you aren't 6'4 well dressed businessman/athlete then you're below their "standards" and I think most sane men know it. But at the same time I can't deny the utility that if I hit off a conversation I can literally be going on a date by tonight IF It all pans out. (Forgive my cynicism, when you've gone this long- you become a little jaded at times) Then there's the height insecurity & self esteem at the root of it. I'm only 5'8/5'9 (without shoes though) and when I'm competing against 6ft dudes it kinda makes me feel: why bother? Self esteem is a whole can of worms and I'm not even gonna dive into that one here. But I'm fit and very proud of the work I've put into my body so I guess I have that. Are there any guys who went on their first date way later than normal? Any tips or content that helped you out? Any books or forums? Any mindsets you adopted? Unrelated self help note: Day#5 complete(in 2 hours) I focused on work, cut back on distractions, and am building a little bit of momentum again but I can't stop here- I have to make more meaningful change. I have to acknowledge what's wrong with my life and what I can do about. Most importantly I have to be focused and consistent- let's get it! This post will go into my journal log since I don't have time to write twice today.