30 Questions Every Gay Thirty-Something Should Ask On First Date When Looking For ‘The One’


So you’ve reached your thirties and you’re still single.  Congrats!  You were smart enough to understand that every guy that sashayed into your life during your twenties wasn’t necessarily supposed to be “The One.”  Lezzz be honest, “young, dumb and full of cum” is NOT a euphemism.

You get to know yourself through dating, seeing and fucking a myriad of guys in your twenties.  Those experiences – the good, the bad and the ugly – leave an imprint in your consciousness as you seriously start looking for “The One.”  You’re more willing to call a spade a spade, raise a red flag, and say thanks, but not thanks in your thirties.  And here’s the reason – you don’t want to waste time dating a version of someone you’ve already dated.  Boy, bye!

You want to separate the wheat from the chaff in your thirties and you don’t have time to dick around, so to speak.  So the next time that seemingly perfect guy asks you on a date, cut to the chase and ask these thirty questions to avoid the pitfalls of your twenties.

  1. Are you married?
  2. Are you married by law?
  3. Are you married by law or otherwise in a foreign country?
  4. Are you gay?
  5. Please define “gay.”
  6. Are you in a relationship?
  7. Are you in a committed relationship?
  8. Are you in an open relationship?
  9. Are you in polyamorous relationship?
  10. Are you capable of being in a relationship?
  11. Please define “relationship.”
  12. Are you emotionally available?
  13. Do you know what an emotion is?
  14. Please define “emotion.”
  15. Have you ever been called “a walking mind-fuck?”
  16. Did you or do you have a drug problem (including illegal or FDA approved drugs)?
  17. Don’t define “problem” in question 12.
  18. Have you ever consumed a case of Miller Light in one sitting?
  19. Have you ever been convicted of a felony?
  20. Does anyone currently have a restraining order against you?
  21. Do you suffer from only-child syndrome?
  22. Do your drive a Prius?
  23. Do you eat meat?
  24. Are you too close with your mother?
  25. Do you currently live with your mother?
  26. On a scale from 1 to Bro, how much of tool are you?
  27. What are you fetishes?
  28. Does your Grindr profile read “Bossy Bottom for Snarky Top?
  29. Do I look like a power top in my Facebook profile pic?
  30. Do you consider me a red flag, and if so, do you accept the challenge?

Your date will either laugh his ass off, sit in silence because he’s mortified you had the audacity to ask these questions on a first date or he’ll storm out in dramatic fashion.  Regardless, his response will be telling and you’re likely to understand your date on totally different level from the get-go.