[Grue3]

This is a depressing read. Here we have a "startup founder" (=relatively wealthy), who isn't that bad-looking, using a complicated script to massively increase his opportunities and he still can't get a date. Is there even hope for the rest of us?

[amackera]

Haha well he got plenty of dates (150 of them), he just never found that special someone.

TBH I think his problem was that he didn't quality his leads well enough.

[vertex-four]

Yes, there is hope. Don't work your life away, and actually get out and do things. Places I've met people: roleplaying groups, kink communities, hobby-related conferences and workshops, local events, completely random social IRC channels. It can take just one off-hand comment on a shared interest to lead to a conversation and a spark.

Also note that the sort of person who finds enjoyment in automating away social interaction is unlikely to be enjoyable to socially interact with.