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Some people have addiction, usually to a product to get some high. Sometimes to food, sometimes to pain, sometimes to emotions, like falling in love. I'm addicted to regrets. I have no self esteem, so I always believe that people hate me or ignore me, and that I don't deserve anything, so I don't take chances. In life, if you don't take chances, no one is going to give it to you, of course you know that one person to whom it happened. That is one person out of a thousand. I know I should try to live to the fullest, but for some reason my sick mind always try to push for the regrets. A party? Let's not go, so we can regret this later. Food? Let's not buy the right thing, or buy the junk one, just so we can regret it later. Let's not exercise so we can regret it later. Let's not ask that one girl and get rejected so we can live with this regret for the rest of our life. Regrets is my addiction, sometimes I chase regrets of things that have not yet happened. I don't like regret, I hate it, it's painful, the word is never positive, you don't have a "I like regretting this or that", if you regret something, you wish it had happen.
I self destruct myself, self sabotaged. As I said, I have no self esteem, I hate myself, so having regret is the punishment I need to keep the cycle of self hate and low self esteem. I also have the staircase wit syndrome, which leads to more regrets.
I'm trying to break the cycle, but I have been like this for so long, that I ultimately relapse, over the most minor things, or the most major ones, I think I'm broken beyond repair.
It gets lonely living with regrets, and no one great has an addiction to regret.
If you feed on regret, you'll be miserable your whole life, and you won't ever achieve anything.
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I think to some extend we all do. Cowardice and regret are bedmates. My best advice is to get some friends to do stuff with, ideally ones that you have a hard time reasoning against. Whenever I do things I consider unreasonable it's usually my best friend who talked me into it and most often I have a blast. But I know exactly what you talk about, the person who impressed me the most was a girl who just did all the stuff I always wanted but never dared to because I feared disappointment.
In the end you need to build some friendships first, so going to work or to university or making some sport and making some friends is really required. If you feel like that's too much, like you really can't break out and are stuck, call the person you consider closest. Best friend, sibling, parent, whomever you feel you can trust the most, talk to them about how unhappy you are with your situation and there's a good chance they are going to be the person that picks you up and puts you back out there.
An important side note:
Excessive self-hatred and feeling stuck are symptoms of a depression, you might be sick and in need of medical help if this is a continuous state of mind. As I wrote earlier it's perfectly normal to have a bad day and ponder about all the missed chances, but if you feel constantly paralyzed and are just holed in, seriously consider asking a professional for help.
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^ pretty much what Archeon said, especially the last part.
It sounds that you're quite depressed in a clinical way and outside help might be a good push in the right direction for getting rolling again. There is no shame in that.
I feel like a good thing you might do as well is pat yourself in the back for small accomplishements. It can go a long way for your self esteem. If you like to sabotage yourself i suppose that you see failure in whatever small things you're trying to do.
Just think about it the other way, if you feel depressed, doing anything seems hard. Just feel proud of what you might do, even if its not that big of deal.
Wanted to exercise? "Hey it's fine, i went outside and walked a bit to get my junk food." I didn't buy healthy food? "It's fine, i feel a bit down and it makes me feel better, i'll try to go for something healthier when i'm in a better spirit."
It's all about seeing the tiny good parts in what you might consider awful and what you'll be likely regretting later on.
Because what's the point of regretting something that's okay, even if it's not great, it's way better than nothing.
Baby steps 
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@ OP
After reading your post, I think there's 2 things that can help with your mindset.
1) You reward system is off. Junk food is junk food, it shouldn't be used as a reward for an accomplishment, nor should you use it to make you feel better about something that you thought was unjust. You are not a dog, don't use food as a reward or punishment. It should just be viewed as fuel 99% of the time, unless you're at a social gathering.
Also instead of focusing on an end result, focus on the action. If you want to ask someone out you can't control what they're going to say, all you can do is your part, the courage to ask. Whatever they respond doesn't matter, it's indifferent. Even if she said yes, you might not end up liking her and just end up wasting a lot of time, maybe you dodged a bullet.
2). Grass is always greener on the otherside mindset. It's helpful to realize that this mindset exist among us all. If you regretted going to the party, know that even if you did go, you would have wished that you stayed at home. So just be content with whatever choice you made at the moment and know that it was the best decision you could've made at that specific time, given the information that you had at that specific moment.
Whatever unchangeable condition that you have that makes you feel bad about yourself don't, such as your looks, your height, your social "class". Non of that was in your control, your fortunes and misfortunes could've fallen on anyone. As long as you're giving your 100% effort at every moment, that is enough. Bill gates, Jeff bezos all gave their 100% on their craft, they both worked extremely hard and also got extremely lucky. Luck or bad luck can fall on anyone, if you're also giving your 100% on everything you do, each decision you make, you have done enough to be just as good as the best of the world.
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EPT
