Really poor quality of shit here, but its still the only and worst.
Once had a bot message me. First bot I'd encountered since MSN messenger about 5 years prior so I fell for it, wasnt primed for it and I was very very drunk at the time. Wasted about 3 hours talking with it, responding to what turned out the next morning to be very obvious non-sequitors. Explaining to "her" that coming to meet "her" that meeting up now, at 2am, was a bad idea etc etc.
2 or 3 hours later and it explained to me that I could visit the website and it needed a credit card but only to verify that im 18.