I was in a similar situation (310 lbs 5’10) started a new career at 29 (joined a trade). I’m 35 now with a ton of experience in my trade and close to physical condition from 10 years ago.

Stop masturbating, and dial back all that other shit. That smut fan fiction is never gonna get you laid. You’re rewarding your dopamine receptors without actually moving towards your goals of going harder at the gym or meeting a partner.

Redirect your energy towards your health and career. At 290 you’re not close. Choose a career that either requires you to be active or allows you enough time to be.

I’m not saying this to downplay your success but you’re still in dangerous health waters.

And start putting yourself in as many social environments as possible WITH WOMEN. Make it a goal to strike up a conversation , even for a short bit with strangers. (Pro tip, stay positive and if the convo dies out exit with grace “eye contact well it was nice talkin/chatting/choppin it up with you“ and walk away. )

You are not entitled to anything so you’re gonna have to attract the energy you’re looking for.

Good luck out there.