One thing I learned, is that, most of the time, someone is only out of your league if you believe they are. I don’t know you (beyond our little conversation here) or her (at all), but it sounds like you have a lot to offer. And, no, not giving her everything, but that part shows me that you’re emotionally available, or, at the very least, willing to be. Although, I don’t know if I would recommend dating or pursuing a coworker, as it can lead to some very unpleasant situations.
Another thing I’ve learned, happiness and success are not actually linked to one another. I know several well-off to bumtasticlly rich people who, I think, everyone would categorize as super successful, and they are some of the most unhappy people. I also know rich people who are happy, and poor people who are happy, and poor people who are unhappy. My point is that money and success won’t make you happy.
Money makes life easier sometimes, but good friends (emphasis on the good), I think, add more happiness than a ton of money.
I think the BetterHelp thing is a wonderful place to start, even if you have to bend the truth a bit to get in. You deserve happiness.
Believe in yourself, and don’t be afraid to be happy–that’s one of the hardest things to do after a stint (no matter how long or short) of depression. Tell yourself every single day that you deserve to be happy and you are going to be happy today. Literally, write it on a stickynote on the mirror “I deserve to be happy, and I will be happy today” and read it out loud (even as a whisper) every morning. Maybe add a phone reminder to remind you of this fact throughout the day.