The Five Toughest Questions

The questions are:


  1. What are you thinking about?

  2. Do you love me?

  3. Do I look fat?

  4. Do you think she is prettier than me?

  5. What would you do if I died?

What makes these questions so difficult is that every one is guaranteed to explode
into a major argument if the man answers incorrectly (i.e., tells the truth).
Therefore, as a public service, each question is analyzed below, along with possible responses.

  • Question #1: What are you thinking about?
    The proper answer to this, of course, is: “I’m sorry if I’ve been pensive, dear. I was just reflecting on what a warm, wonderful, thoughtful, caring, intelligent woman you are, and how lucky I am to have met you.” This response obviously bears no resemblance to the true answer, which most likely is one of the following:

    1. Baseball.
    2. Football.
    3. How fat you are.
    4. How much prettier she is than you.
    5. How I would spend the insurance money if you died.
    6. (Perhaps the best response to this question was offered by Al Bundy, who once told Peg, “If I wanted you to know what I was thinking, I would be talking to you!”)

  • Question #2: Do you love me?
    The proper response is: “YES!” or, if you feel a more detailed answer is in order, “Yes, dear.” Inappropriate responses include:

    1. I suppose so.
    2. Would it make you feel better if I said yes?
    3. That depends on what you mean by love.
    4. Does it matter?
    5. Who, me?
  • Question #3: Do I look fat?
    The correct answer is an emphatic: “Of course not!” Among the incorrect answers are:

    1. Compared to what?
    2. I wouldn’t call you fat, but you’re not exactly thin.
    3. A little extra weight looks good on you.
    4. I’ve seen fatter.
    5. Could you repeat the question? I was just thinking about how I would spend the insurance money if you died.
  • Question #4: Do you think she’s prettier than me?
    Once again, the proper response is an emphatic: “Of course not!” Incorrect responses include:

    1. Yes, but you have a better personality
    2. Not prettier, but definitely thinner
    3. Not as pretty as you when you were her age
    4. Define pretty
    5. Could you repeat the question? I was just thinking about how I would spend the insurance money if you died.
  • Question# 5: What would you do if I died?
    A definite no-win question. (The real answer, or course, is “Buy a Corvette.”) No matter how you answer this, be prepared for at least an hour of follow-up questions,
    usually along the these lines:

    • Woman: Would you get married again?
      Man: Definitely not!
      W: Why not, don’t you like being married?
      M: Of course I do.
      W: Then why wouldn’t you remarry?
      M: Okay, I’d get married again.
      W: You would? (with a hurtful look on her face)
      M: Yes, I would.
      W: Would you sleep with her in our bed?
      M: Where else would we sleep?
      W: Would you put away my pictures, and replace them with pictures of her?
      M: That would seem like the proper thing to do.
      W: And would you let her use my golf clubs?
      M: Of course not, Dear. She’s left-handed.