I'd be very unlikely to accept a date from a random stranger, so I think your approach needs to change. I've only ever dated one random - and that's waaaay back when I was 17 and wasn't so good at putting off random men.
You're better off approaching women who you have something in common with. For example, a friend of a friend at a party. Or someone from your sports club/gym...or whatever hobbies you have. And don't rush asking for a date. Get some type of rapport happening before you ask about exchanging phone numbers.
Never regret anything that has happened in your life. It cannot be changed, forgotten or undone. So, take it as a lesson learned and move on.