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.

I don’t have enough enough money to move into my own place, and even though that’s my goal, that’s what I’d define as success, I’m not sure that’d make me happy

It wont. You'd be lonely then.

That said. What keeps you centered? What keeps you from burning out?

just a little bit of flirting with my coworkers

Dont do that. Its messy. Dont shit where you eat or put off the vibes. You gotta separate it out.

I'll asl again, What keeps you centered? What keeps you from burning out?

gonna be honest. Sounds like a shit therapist anyway. Theres tons of em, high on education low on experience or worse, more fucked up and got into it trying to fix themselves. Id bet my left nut betterhelp is chock full of em too, but it wont hurt to look, id still say keep it local if you can. If you are at that point, keep looking though. A decent one that clicks can do wonders.

Personally, i find what helps me is

1. A good sleep routine. Not drunk passed out good sleep, but solid 8 hours. I take some meds that help that arent habit forming and can be stopped at any time.

2. Exercise. Even just walking and podcasts. It helps clear your mind and the heartrate.

3. Some un-work-related hobby that I can get frustration out with. You dont even have to be good. Musical instruments, working on shit/fixing shit, exploring/hiking etc etc. Basically anything and it can always shift around. Just something to do in downtime that engages that part of your brain.

NGL, 2 and 3 can be hard. I often have to push through the "fuck this, whats the point" or "dont wanna be up doing this shit right now" parts at the beginning, but 9/10 its worth it. Once i stopped chasing women and just focused on 3 things start coming naturally. You wont even need to "flirt" its where the "just be yourself" comes from.

And before you say "ya ya, you dont know me". I went from living in my car in college/young adult hood to making solid money with a family. Its doable. The depression never goes away, its like addiction. But you gotta learn how to deal with it and keep it in check. A good therapist can help you find that. If they are just driving you to meds or something, ditch them unless you are like full on legit bi-polar or something (then you gotta be on meds, it is what it is)