No I've never tried dating a chat bot, and I wouldn't. Your therapist sounds unprofessional and like an idiot. I don't care how much she charges. She's giving you bad advice. For what its worth, I've seen horribly cruel / abusive / messed up therapists that did more damage to me for a lot of money. The good help I've actually gotten was through a clinic that was free of charge to me. So lots of expenses doesn't equate "good" or "professional" or "best." If it were me, I'd find a different therapist.