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

This is the second 20 of 40 questions to ask on the 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

21) When was the last time you saw a movie that made you cry?

22) What’s been the most significant or best years of your life so far?

23) Who has been the most influential person in your life?

24) If you were stranded on an island and could only take 3 things with you, what would they be?

25) What do you wish you were better at?

26) What is the #1 item on your bucket list?

27) If you could wake up tomorrow anywhere in the world, where would it be?

Level 2

28) When’s the last time you were really jealous? Why?

29) At what point did you realize you were attracted to me?

30) What was the worst first date you’ve had?

31) If you could name 3 things about yourself that are uniquely attractive – that have nothing to do with your physical appearance – what would they be?

32) What kind of things do you imagine doing but haven’t yet let yourself try?

33) If everyone looked the same what would make you stand out?

Level 3

34) How good a kisser are you on a scale of 1 to 10?

35) If we were in kissing school, what grade would you get?

36) If you could make out with someone for 3 minutes and no one would ever find out, who would it be? Why them?

37) On a scale of 1 to 10, how dirty is your mind?

38) Would you ever have a threesome? Have you had one before?

39) What do you like to do after sex? Cuddle? Smoke a cigarette? A cigar?

40) You know what, occasionally I think a girl just needs an evening of passion. If that were to happen, how do you think it would start?


Where’s your favorite place to be kissed?

There you have it.  The final 20 for a total of 40 awesome first date questions. I hope you find them helpful. See you in the next post.  God Bless.

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