Awkward questions to ask a guy

+65 votes
asked Oct 11, 2015 in Relationships by Gemma (820 points)
I’ve been going out with this really nice guy for a few days now. He’s a good talker and he encourages me to ask questions every time we’re together. I don’t want to turn him off this early in our relationship so I want to know if there are awkward questions to ask a guy that I should avoid?

6 Answers

+15 votes
answered Dec 10, 2015 by AnneWoollaco (360 points)

Most guys hate talking about themselves or anything else, so be happy that your man is actually encouraging you to ask questions. I suggest that you take him up on his offer and grill him about all the things that you think are important to your relationship. If you really want to know him, don’t go babying him with safe and harmless questions. I say go for the guts and throw all those awkward questions to ask a guy that you can think of.

Here are a few questions to start your inquisition:

  1. Do you ever fantasize about having sex with any of my friends?
  2. Would you kiss a guy in the mouth for $10,000?
  3. How often do you visit pornographic sites?
  4. Have you ever had any sexually transmitted disease before?
  5. Who is better in bed, me or your ex?
  6. Do you still text or call your ex-girlfriend?
  7. Do you fantasize about me when you masturbate?
  8. Have you ever cheated on any of your ex-girlfriends?
  9. How much is your take-home pay?
  10. How long have you gone without taking a shower?
  11. What would you do if you catch me flirting with another guy?
  12. Have you ever been involved in a bar fight? Who won the fight?
  13. How many times do you urinate at night?
  14. Who is your favorite sexy actress or celebrity?
+9 votes
answered Nov 25, 2015 by DemiZahn2692 (350 points)
I totally agree with the assertions that responding to sexual questions are always awkward for a guy. But in my opinion, it pales when compared to having to answer financial questions from your girlfriend. In the first place, why is she so keen about your money? Unless she is looking to enrich herself by hooking up with you, I don’t understand why she should pursue topics about your salary and credit ratings this early in your relationship. I think it’s okay if a guy volunteers information about those things, but if not, it’s just plain greedy for a girl to ask about them.
+8 votes
answered Oct 16, 2015 by erika (680 points)

I don’t want to judge about your motives for asking any question about your guy’s sexual life or finances. After all, he was the one who encouraged you to ask, so go ahead and do it. Here are my contributions if you really want to nail him on the spot:

  1. Have you ever get fired from work?
  2. How much do you donate to charity?
  3. Do you have life insurance?
  4. How long does it take before you lose interest in a woman?
  5. How much is your net worth?
  6. If our relationships become serious and we agree to marry, are you willing to sign a prenuptial agreement to separate all our assets?
  7. Would you ask me to sign a prenuptial agreement before we marry?
  8. Are you sure you don’t have children from previous relationship?
  9. How much of your income goes to child support?
  10. Are you still friends with your ex-girlfriend?
  11. Would you leave me for a more attractive woman?
  12. How many kids do you want to have with me?
  13. Do love your work?
  14. Are you willing to leave your work and travel around the world with me?
  15. How do you feel about transgenders?
  16. Will you pay for sex?
  17. Would you stay close to a gay friend who openly admits that he’s attracted to you?
  18. Do you still borrow money from your parents?
  19. How often do you go broke in a year?
  20. Are you sure that your roommate is a straight guy?
  21. If I was a prostitute and you saw me on a club, would you pay to have sex with me?
+2 votes
answered Dec 4, 2015 by CalebIrons4 (200 points)
If you haven’t had sex yet, just ask him about the length of his penis and that’s all about it.
+1 vote
answered Oct 22, 2015 by KathieKorff9 (230 points)
I don’t know about you, but all questions about my exes make me nervous. I really hate a girl who feels that she has to know everything about my past relationships. I mean, c’mon, either I’ll tell her the truth and she’ll be hurt or I’ll just lie about everything.
0 votes
answered Nov 17, 2015 by Estela (740 points)

Basically, any question about sex and money will make your guy squirm on his seat. Here are a few awkward questions to ask a guy you should avoid if you don’t want to offend him.

  1. When do you prefer to have sex, in the morning or in the evening?
  2. Did you ever engage in any sexual act in exchange for money or favor?
  3. Do you like to have sex in the shower?
  4. How often do you watch porn?
  5. Have you ever said something embarrassing to your boss?
  6. How do you like your sex partner, passive or aggressive?
  7. Do you have a secret crush on any of your friends?
  8. What are three of your favorite sexual fantasies?
  9. Would you marry for money?
  10. Can you tell me your most shocking sexual experience?
  11. Have you ever gone bankrupt?
  12. What is your credit rating?
  13.  Do you have any homosexual feelings?
  14. How many one night stands do you have?
  15. Have you been sexually abused when you were young?
  16. Have you ever visited, or bought something from, an adult store?
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