Dating Advice For Men: Questions To Ask On A First Date (1 of 2)

This is the first 20 of 40 questions to ask on a first date. The questions escalate in intensity from Level 1 to Level 3.

Level 1 questions are best for the beginning of the date. Level 2 questions a good for the middle of the date. Level 3 questions are for the end of the date or whenever you decide it’s time to Phase Shift (transition to intimacy).


Level 1

1) If you had all the money in the world what would you do?

2) You seem like trouble. What was the last illegal thing you did?

3) What are 3 things you want to accomplish before you die?

4) What is something you’ve done that you are really proud of?

5) What is the most spontaneous thing you have ever done?

6) Tell me something that most people wouldn’t know about you?

7) If you could go somewhere, where money and time were no object, where would you go?  And what do you think you’d enjoy the most?

8) So, we’re on my couch. We’ve known each other for six months now and we’re watching TV. What are we watching?

Level 2

9)  What was your first impression of me?

10) What characteristics do you want in a man?

11) When did you realize you were first attracted to me?

12) When you really want to cut loose, escape, and indulge yourself, what kind of things do you imagine doing? 

13) What qualities do you find attractive in guys?

14) What’s the one thing you can’t say no to?

Level 3

15) Are you a good kisser?

16) What do you think makes for an absolutely fantastic kisser?

17) Do you consider yourself a great lover? Why?

18) Have you ever been with a girl? Are you attracted to women?

19) What do you value most in somebody you’re sleeping with?

20) Let me ask you something… When you’re really attracted to someone, how do you know?  In other words, what signals do you get from yourself inside that allow you to realize you’re really attracted to this guy?


Where’s your favorite place to be touched?

That bonus question is one of my favorite questions to initiate or escalate a phase shift. That’s all for now. Next up: another 20 first date questions. God Bless!

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