5 Of The Toughest Questions Women Have Asked Me

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“Does this dress make my tushie look big?”

This inquiry is one of the cruelest questions women continue to ask men. The answer will always be YES and if you protest with, “Are you sure you’re not just saying that?” I will counter with,  “Hun, will I ever lie to you about your enormous tushie?”

I’ve been a bachelor for seventeen crazy, fun and sometimes miserable years. Name any tricky question women love to ask and I guarantee you, I’ve heard it before.

I’ve survived flirty questions like, “Why are you obsessed with my boobs?” to serious ones like “Is my best friend prettier than me?”  I can answer almost every generic “getting to know you” question in my sleep.

Women, in general, are very curious creatures and the reason for their curiosity is simple; men are mysterious and we barely allow anyone close to our inner thoughts and our past.

Some women have adapted to our propensity to tip-toe around questions and conjured up some interestingly loaded questions.

Five of such loaded questions totally spooked and left me speechless and running for the hills.

Without much ado, here are the five toughest questions women have asked me on the dating scene.

Question One:

Her: “Do you collect any trophies or keepsakes from women you have sex with?”

Me: Total silence

My silence pretty much gave me away. Hey, don’t judge but I do have some waist beads and other unmentionables stashed away somewhere.

I was once with a woman whose dress was so tight, I had to go find a pair of scissors to help her out of it.  Of course, I had to keep the shredded dress just for kicks and grins.  Come on! How many times does a man get to liberate a woman from her tight clothes with a pair of scissors just before sex?

I was totally not ready for this question. The woman who asked must have been into some fetishes like me. How else can she come up with a freaky question like this one

Question Two:

Her: “We have a lot of mutual friends on Facebook, don’t we?”

Me: “Yeah, we do.”

Her: “So how many of my female mutual friends do you personally know?”

Me: “Uhmmmm, maybe 5.”

Her: “Oh great! Who are they? Also, out of the 5, which ones have you hit on before or slept with?”

Me: “Wait, what?”

This question sounds really innocent but it took me a minute to wrap my brain around where she was going with this inquiry.

First of all, she set up the sequencing of questions in a way which forced me to actually look at every single female mutual friend we had.

Secondly, I had no clue I had actually hit on two of her friends’ years earlier until I looked.  I noticed she paid very close attention to my non-verbal reaction to every picture I checked.

Most women absolutely hate it when they start dating a guy and walk into a friend who goes like, “Hey, your man came after me.” Or “Your man came after me and I turned him down.” Or “Your man and I used to have a “thing.”

This question was a clever way for her to figure out if I had been romantically involved with any of her friends.

Question Three:

Her: “Hey, do you remember the names of all your exes?”

Me: Nervous laugh followed by a spontaneous scalp inch

I am a pro at answering questions like “How many women have you slept with?” and “How many exes do you have?”  Up to that point, no one had asked for names. Her ask for names made the question personal for me.

Of course, I could not remember the names of all my exes so I had to develop a brain freeze and zip up. Her question was a clever and twisted version of “How many women have you dated?’

Question 4

Her: “What do you think about when we’re having sex?”

Me:  (Long pause) “What kind of question is that?”

Ah! Women, they notice everything. This question got me flat-footed because she was on to something.  The truth is, I mostly pictured one of her hot friends during the act.

She pointed out that I hardly look at her when we have sex and I keep her on all fours for the most part.

Bonkers! I was definitely busted but I was not about to respond with something like; “I’m sorry Esi, but I’m mostly thinking about Akua’s perfectly shaped boobs every time we have sex.”

Question 5:

Her: “How long do you think we will be together?”

Me: “I don’t understand the question.”

Her: “How long do you think our relationship will last?”

Me: “Can we discuss this question later?”

Some men, myself included, dread women bringing up marriage until we’re ready to take the relationship to the next level.  Most men can tip-toe around this question and come out just fine.

This question, however, did not explore marriage possibilities.  She wanted to know if I had long-term plans for the relationship. Instead of asking the same boring and generic “are you going to marry me?” question, she took a different and very clever approach.

How do you respond to a question like that when long-term plans have not crossed your mind yet? If I say I don’t see us ending the relationship anytime soon, I may be committing to marriage.

Consequently, I can’t respond with, “I really like you and I truly enjoy every second we spend together. But, I don’t think we will make it past 6 months.”

Every guy will be hit with a loaded and tricky question at some point in their lives from a woman. My advice is; don’t panic, just breathe.  If you don’t know the answer, its best to just shut up. Don’t lie either because that is disrespectful.

Then again, how you respond to a loaded question will also depend on how much the woman wants to torture you.

Keep the tough questions coming, Ladies.  Y’all doing very good!

By Kwadjo Panyin

Model Depicted: Ethel

Author: Kwadjo Panyin

Kwadjo Panyin is a Ghanaian born relationship and lifestyle blogger located in Los Angeles, California. He holds three degrees; a Bachelors degree from Rutgers University in New Jersey, an MBA from Franklin University in Ohio and a Masters of Science degree from Northern Kentucky University in Kentucky. Kwadjo is a business professional who blogs for fun. His articles are about the challenges of dating and relationship anomalies. Writing, blogging, world travel, and photography are his favorite hobbies.

4 Comments

  1. Interesting questions and very fascinating answers. Nicely done.

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