TLDR: Just because you made gains in life, doesn't mean you'll make gains in confidence. Keep acting like the loser you always were and you'll keep being treated like it. You are your own worst enemy - don't let yesterday's failures dictate tomorrow's choices. Break free of your comfort zone.
Along your journey down the path of self-improvement, you may find that a small part of you yearns for the past, painful though it was. But why would you want to re-live those hurtful rejections? Why would you want to experience again what it was like to be her BP beta, friend-zoned shoulder to cry on while she fucked Chad and got played?
It's not uncommon for prisoners who've spent most of their lives behind bars to crave returning to their cells, counter-intuitive though it may seem. Maybe it stems from a desire to return to familiar, or perhaps it comes from a compulsion to re-live the traumas and pains of the past such that we can finally reconcile them.
Take also the case of the hot girl with daddy issues. I'm sure most of you who have been around the block have encountered a girl like this. Her father was a cad - he abused mom and abandoned them both. Girls like this often find themselves drawn to the same emotional characteristics of her father. Deep down, part of them wishes to find a mate who is likely to abuse or abandon her, just like daddy did. Maybe then, her hamster figures, she can finally fix what went wrong all those years ago and heal the emotional pain from her father's rejection of her. Of course, we all know, that's not what happens; instead, she re-lives her past trauma again and again, until it becomes a pattern so familiar that - painful though it may be - it becomes her new comfort zone, and difficult to get out of.
Momentum and inertia are powerful forces when it comes to human motivation and behavior. Like the saying goes, you make the habits and the habits make you. As we repeat a behavior over and over, the neurological mechanisms involved find their pathways strengthened and reinforced. It's why addictions are so hard to break, but conversely, it's also why once we adopt a habit like lifting and perform it for long enough, it no longer requires nearly as much discipline to perform. Work hard for long enough, and eventually it won't feel like hard work - it will just be what you do.
You can probably see where I'm going with this already. If you're like me, you didn't have much luck with women growing up. But when you swallowed the red pill, you made a solid commitment to improve your life by any means necessary and (hopefully) you've been putting in the hard work ever since.
The thing about changing yourself is, very often you're the last person to see it. This can go both ways. Take the case of a bumbling alcoholic who drinks himself into a blackout on a regular basis. By the time he realizes what a problem he has, he's usually the last to know. Everyone around him has already figured it out.
But the same goes with improvements. A frequent complaint of fat guys who have lost a lost of weight, or skinny guys who have built a lot of muscle, is that no matter how much they improve their fitness and physique, they still feel like the person they always were. And so they're never big enough; never lean enough. But if they just keep improving, just a little more, maybe then they'll finally have a body they can be proud of.
The reality is, this is the kind of thinking that leads to steroid abuse, to eating disorders, and to body dysmorphic disorder. Obviously you want to lift, eat healthy, and hone your physique, but you don't want to get caught in the trap of investing your ego into succeeding at achieving an impossible standard of aesthetic perfection that will always be just out of reach.
But let's bring the discussion back to women, because I think that's the most important part of this discussion. These are the kinds of behaviors I see the most:
Assuming rejection before you've even tried. Assuming a girl will be stuck up/dismissive/unfriendly if you approach. Assuming a girl thinks she's out of your league, or that she's superficial or only dates rich guys.
Assuming that you can't hold her attraction. I'm talking about anxiety when she doesn't answer your texts, your heart sinking if you see with another dude, assuming she wants to fuck your friend when you introduce her, bringing her to public places and worrying she's going to go home with another guy. The insecurity and neediness that you project will send things into a negative feedback loop of her shit-testing you, you failing those shit tests and losing frame, and her eventually being repelled by you and attracted to other guys.
Assuming she intends to put you in the friend-zone / make you into a beta orbiter. So if she complains about another guy she's seeing, you immediately assume it's because she wants to LJBF you, ignoring the possibilities that she might be rationalizing a decision to cheat on him with you or giving you an opportunity to demonstrate superiority.
Assuming she only wants you for your money. I had this happen to me recently, actually. A girl I met at the bar asked me if I wanted to 'take her out for drinks.' My mind jumped immediately to 'oh, she just wants someone to take her out for free drinks, she's not actually attracted to me.' That couldn't have been further from the truth. Not only was she attracted to me, but she paid for half the tab without being asked to do so.
The trouble with this kind of stuff is that they're all self-fulfilling prophecies. As you spend more and more time behaving like a guy who thinks she's going to leave you, a guy who thinks that she doesn't see you as a worthy mate, her intuition is going to sniff out your weakness. Women can smell this shit a mile away, I'm telling you - nature designed them that way.
And trust me, when she picks up on the fact that YOU don't think you're good enough for her, on an emotional and instinctive level she's going to start to feel the same way. After all, if even YOU don't believe you're a worthy mate, why should she?
Look, your past failures don't define who you are as a person. Resist the temptation to re-live the mistakes of the past and make a conscious effort to move forward at all time - don't look back.
Sometimes demons from the past continue to haunt us long after they've already been conquered. One thing that often surprises people who lose substantial amounts of weight is how little difference it made in their psychological experience. They figured once they lost all this weight, they'd magically transform into this confident, empowered person. Frequently, they are disappointed to discover that they remain the same person they always were albeit with a shiny new exterior.
People don't like to hear me say this on this sub, but I stand by it: confidence comes from within. Supermodels are notoriously some of the most insecure people on the planet. Many great intellects feel stupid. Many of the best artists and most creative musicians have been their own worst critics - sensitive to criticism and yet dismissive of praise. Jimi Hendrix famously said he didn't like compliments because he found them distracting. Stanley Kubrick is said to have stayed in bed for days in a dark depression following an unsuccessful early screening of 2001: A Space Odyssey.
Richard Nixon, who as US President became what is considered to be the leader of the free world, and yet biographers describe him as a perpetual outsider, someone who felt alienated throughout his life, someone who never felt accepted. An elected President who felt like no one accepted him. Think about that.
And so what if your issue is that you feel like you're a loser with women? How are you going to fix that? Well, if you think that's going to change when your notch count hits 10... 50.. 100, you might want to think again. If you think you'll feel like a stud when you finally have abs, you might be surprised.
Looking for validation externally is like filling a bucket with a hole in it. The only way you're gonna stop feeling like a loser and sabotaging your opportunities at success is if you work on your inner game: managing your emotions, practicing self-discipline, mindfulness and self-awareness (meditation helps a lot with this), cultivating an attitude of stoicism, and behaving with self respect.
If you go looking for validation from the outside world, then you're no better than some Instagram whore who shamelessly posts pics of her tits and ass for the world to see all in the hopes of obtaining more likes and followers. The only difference is where you get your validation.
Look, success is scary. We don't like to admit that we might be afraid of success, but we are. If failure is all we've ever known, then failure becomes our comfort zone. And if we're not careful, we'll screw ourselves over simply to stay in our comfort zone. We'll set ourselves up to fail because failure is all we've ever known.