Advice on asking a girl out on a date.
Here's my advice Jay!
1. Send a text asking her to do something low-stakes
Just like you would a friend. I read in Logan Ury's book How to Not Die Alone that a night date to get drinks is better than coffee during the day.
2. Home-court advantage
This is my own thing I made up: I only go on first dates with people at places I've been to and like before. Home-court advantage has always worked for me. It's real!
3. Dress for success
To me, regardless of the outcome, you gotta put your best foot forward - it shows manners and respect. They did agree to spend time with you after all. Just don't overthink this.
Watch this. She is the best:
4. The Brad Pitt rule
From the Art of Manliness: https://www.artofmanliness.com/people/relationships/the-brad-pitt-rule/
Basically, if you ask and she says she can't make it but is interested, she will suggest another time - just like if Brad Pitt asked her.
5. Be genuinely interested
Ask her questions about things you really want to know, just don't do it like in a job interview or how a journalist would interview.
6. Try to not worry about the outcome
This is very hard to do, but the objective should be to have fun. If you do everything right, but don't get a second date, then there really wasn't anything you could do.
7. Pay for the first date, never go dutch
This one I learned from Kevin O'Leary's Cold Hard Truth. No confusion or fussing. It's easy.
8. Get there 15 minutes early
You don't want a girl sitting around by herself waiting for you - that's awkward and unsafe for her. Better you get there first and wait.
9. Do some research with the info she gave you
If she told you things during the first conversation, do some research about them. If she gave you her social media/website etc. take a look at those before you meet her again.
10. Remember, she wants it to go well, too
11. End the date if it's not going well
As soon as you feel uncomfortable, call it night. Or if she does something that would make her a crappy person, do what @JamesAltucher says and immediately get up from the table (pay the bill of course).
12. Self-compassion the whole time
If you're nervous, tell yourself she is, too. If it goes bad, tell yourself that at least you got this far, and you'll get another date again.