I'm not single, and I haven't been for the past two years. I will admit that i'm not like some people on this thread who have been single for 5+ years or even their entire life. I will say that I have enough confidence now to think I'm attractive. Tall, good jaw, decent facial features etc. Why is that important? I don't mind a little PL since it represents the past me.
I wasn't always this way. Sure I was always the "tall kid", and my facial features have always been strong since puberty but that didn't matter to me. Like most other teens I was heavily insecure for all the wrong reasons. I had very shitty luck with girls when I was younger by acting like some wimpy faggot and treating them like eldritch unknowable beings that I should be lucky if even the ugly ones consider me. The few that did date me were either ugly, or they were hoes that just liked me for my looks who had shitty personalities that very quickly left me for acting like a simp. Occasionally I would find one that was a good woman who still left me for being dumb. Those were the worst ones that really gutted me at the time.
I was lucky if a relationship lasted a week or a month, nevermind 2 fucking years. I would look at my male peers with their pretty GFs that they've been dating for 1-3 years at that time and get jealous, and further fall into the dark pit of insecurity. I thought I was one ugly motherfucker, and no amount of the objective reality in the mirror with my own two eyes changed that. My logic was pretty simple at the time "I can't be attractive since no one but uggos want to date me". I was wrong, and its because I started with insecurity it ended up spiraling very out of control until the last couple of years. Another really shitty thing that happened is that good looking women would send me signals and I was either too inexperienced to pick up on them, or if I did too insecure to do anything but either disbelieve it or freeze up. I was single for 3 years after turning 18 until I started landing dates again.
Good looks only get you so far, and if you act retarded you can set yourself up for a world of failure regardless of how pretty or ugly you are.
No I do not believe "only personality matters" because that's naive feel good BS. However it IS possible to be ugly and to find a decent looking woman that's not some gold digger. Of course this depends on how ugly you really are since some people are just "meh" to "holy shit what type of fucking mutant is that?" You must have realistic expectations and standards. Don't settle, but don't start batting out of your league if you know you aren't confident. Baby steps my friend.
Take it from me. If you think you "missed out" during your youth with dating young girls/guys and you're far behind other people I will say that you're wrong. All those shitty relationships in highschool and early college only served to give me some experience in what to look out for, and given me a tiny boost to confidence because at least I can find a date, no matter how bad they are. Those guys and girls I mentioned that slayed during highschool and stuck with their "sweethearts" had relationships that crashed and burned. Some of them settled and stayed with very shitty partners that cheat on them because they haven't dated anyone else and they're afraid to be alone. Only a small handful have stuck with people that have meaningful successful relationships. 16/18 year olds are retarded and don't know what a good relationship looks like. Look to the future and present, not the past.
How did you overcome the insecurity and fear of rejection. The gym used to work for me but it does not really help anymore.
The insecurity part is the tough one. It's hard to overcome fear of rejection if you haven't overcome insecurity first. How did I do it? Well discipline helps out a lot. You already show mental and physical discipline by regularly going to the gym. Now you just need to increase your mental discipline even more. What makes you insecure? Is it because you "sperg" out too much and say stupid things? Do you think you're ugly? Maybe you got bullied? I don't know and only you know, so think about it. Once you know think to yourself "what can I change, and how would I go about it?" Its OK if you don't know the answer to that at the time. Just keep thinking about it until some solutions come up. Chances are the things you feel insecure about can be changed. If you're ugly you can still groom yourself and smell nice. If you're socially inept you can work on it. and get better unless you have extreme autism, and I doubt you have that if a girl is interested in the first place. Don't sweat about how much progress you seem to be making. You have your whole life ahead of you, and as long as you slowly make some gains you will eventually be fine.
One big thing about overcoming insecurity and rejection is that you just have to do it. You're brain will be screaming at you when you start feeling uncomfortable, and want to make the next step. Don't try to push it out, don't try to completely ignore it. That will just make it worse. Realize that its there, and breathe for a second. Think to yourself "I know I feel uncomfortable, but I will be fine". If you truly like this girl and want to move forward you must overcome yourself. You have no choice. It's either do or die. Once you start slowly overcoming your fears the big fears get easier to take on. Eventually you will do this enough that even when you do feel anxious and insecure you will know what response to take and stay calm.
Update things are going better even though a sperged out a bit. I was at her house tonight and we sat and watched movies in the living room and it was a good night with cuddling. Then she said it was bed time and she got up and went to her bed and I she was sitting there with her laptop expecting me to stay I think and I said well I am going to head home like a fucking idiot.
Hey man we all make mistakes. I still fuck up with my girl after two years, so its expected. Don't beat yourself up for past failures, just learn from them. I no longer think about my exes unless its very specific topics like this. It's just past experience I can use to better my life. I will say don't be afraid to lose someone, even if you think they're perfect. (which they aren't) If things go bad life goes on and you can use it to grow, and get a better relationship. I've been in the exact same boat. I've had girls that might as well been spreading their legs and I still failed to take the hint and fucked it up. I used to say "god I'm so fucking stupid" now I'll say "oh well".
Remember, if she didn't like or trust you she wouldn't have you hanging out with her alone in her house. She has already shown she's at least interested in you, all you have to do is calm down and let things happen that are within your and hers boundaries. If you're unsure about her boundaries then just ask. If I can overcome it you can too brother.
Not sure what you guys think of my advice, but if you're an insecure guy that needs help just PM me. I've been there too and might be able to give another perspective.