This is not advice for someone trying to evolve a multi-year friendship into a romance (though I could make a list for that). This is for a guy who's always meeting new women, but it never quite goes anywhere.
  1. Ask her out!
  2. Not, "do you want to hang out?" or "let's see a movie!"... Legitimately say the words; "Can I take you out on Friday?" or "I'd like to take you out next week."
  3. Seriously, that is the advice.
    I know it sounds obvious. And yet I see the male friends in my life screwing this up all over the place.
  4. If she's not interested, at least you'll know.
    Better than staying in a "friendship" where you spend months hoping one night you get drunk and kiss. And maybe you do, but neither of you is quite sure what the other wants so you play it off as a crazy mistake. Trust me, protecting your ego is your worst enemy here.
  5. And if she says, "yes, sounds fun" than you have clarity that you have a shot.
    Isn't that better than spending a whole dinner at Terroni* wondering whether or not you are on a date? *or your city's date-ambiguous Italian restaurant.
  7. Pick the place.
    Aziz Ansari is all over this in his book. Nothing is less sexy than hemming and hawing about schedule and location.
  8. Ask her questions!
    Again, obvious. And yet, somehow not.
  9. Pay on the first date. I know this is controversial. Of course read your lady friend's vibe on this. But speaking personally, I think the person who did the asking out should pay.
    It's generous, not paternalistic.
  10. If you had a good time, call or text her THE NEXT DAY. I genuinely believe we could all use a dose of effusiveness in our dating lives. The worst relationships I have been in have consistently been the ones where in the beginning I wasn't totally clear what the other person wanted.
    That initial timidity/self-protection lingers in a relationship in a toxic way.
  11. Oh, and both men and women: if you drive separately, don't valet. This may be a uniquely LA issue, but seriously, think ahead if you're hoping to visit make-out city :)