Sounds like you got the right idea mate, by practicing talking to strangers to build up your social and conversational skills.
Now you should start speaking to strangers who are younger, and hopefully female and attractive
And remember:
It does not matter whether a move works or not - be a guy that makes moves.
You learned from your mistake, next time make a move and take a chance when an idea like that comes to you. Not knowing what would've happened is worse than if a girl politely doesn't accept.