Really wish I could give some positive advice, unfortunately I can relate to a lot of what you say.
The last couple of years have been very hard, I've been dealt some quite harsh home truths about were I'm at right now in my life.
I wouldn't describe myself as an outcast as such, but my whole life I have struggled to form genuine relationships, most probably because of depression and my unhealthy ways of coping with depression.
I'm at the stage now were I can't be bothered to make an effort, It feels kinda good in a way because I feel the pressure is off now.
Hopefully I'll get in a more positive state of mind soon and start making an effort again. All the self help books I've accumulated over the years have gone in the bin though, I certainly won't be buying anymore.
Actually I'm developing a "not giving a shit attitude" which feels good
Sometimes we just need a bit of luck, sometimes we just need good things to happen. You're still young at 28, plenty of time for good things to happen for you