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Top 15 Worst Questions You Should Never Ask On a First Date


A Little Insight For Guys

Unfortunately I am sad to reveal that all of these questions have in fact been asked of me by a guy on the first date. I am dead serious some guys do not have a clue of how to woo a woman. So part of the reason I created this article was for other girls to laugh at the idiocracy of failed attempts of men trying to flirt. The other reason I created this article, was for the guys that have made this mistake before to understand that the reason their love life might not be flaring so smoothly, is due to them asking questions such as these on a first date. Some of these questioned should never be asked EVER.


1. How Old Are You?

Alright, two situations apply where this question is inappropriate. The first scenario is, if a woman is 30 years old or older, men should be old enough to know better by now than to ask a woman this question on a first date. Women 30 years of age and older are uncomfortable revealing their age until they are comfortable with the person. If a guy asks a woman over thirty her age on the first date, it is an ultimate turn off. A guy will struggle trying to bounce back from that mistake, and more than likely, he just crushed his chances with that woman. The second scenario is, when a man twice a woman’s age, old enough to be her father, approaches her asking her age. There are not many women who feel this is appropriate. For example, if I am nineteen, and you are between 35 and 42, when you ask my age, I am going to answer I am fifteen. By me stating I am underage, I am hinting to a guy, and attempting to get him to leave me alone. By the way, I was making an example; I am not nineteen years of age. My age is irrelevant.


2. Are You Wearing Underwear?

If you seriously just asked a girl if she was wearing underwear, you have immediately crushed your chances of finding out. You have officially just come off as a total pervert. If you were trying to hide the fact that you were hoping to “get laid” on the first date, you have just failed. Maybe if the girl had thought you were genuine and truly interested in her for her personality, you just might have “gotten lucky.” But she’s on to you now, and knows you are just looking to “get in her pants.” Kiss that opportunity goodbye. Honestly, that is what you get.


3. How much do you weigh?

Everyone knows women are self-conscious and insecure about their weight. Almost every girl even if they are thin as a model, will lie about their weight. Whatever they claim is their weight, add ten to fifteen pounds, and that is their actual weight. For instance, height plays a huge factor in weight. I am 5 foot seven and a half inches tall. I keep thinking I should be 120 pounds like most girls, however, I am a head taller than most girls, and that head isn’t full of air. So even though I am thin, and my weight matches my height, and I have curves that fill me out, I am still self conscious to reveal my weight. It’s quite strange. But this is just how women are. Asking a woman this question is an automatic way to make her feel uncomfortable. If you were planning on going out to eat, you can plan on canceling that, she won’t want to go anymore. If you asked this question in the middle of dining out, that is even worse, you have just ruined the meal, and possibly the date itself.


4. How many sexual partners have you had?

That is very much none of your business. This just makes a girl uncomfortable, and she will think you are judgmental. Are you trying to weigh your chances on “getting lucky” by the amount of guys that already “got lucky” with her? Few partners’ means she’s going to be “hard to get,” the guy might not feel up for the wait. Or he might be the slick charmer type who enjoys a challenge. If the girl has had quite a few partners in the past, the guy may get the wrong idea. So again, this is certainly not the question to ask on a first date. At least wait a month to ask this question, and tread lightly when you ask it, be sure she is comfortable with you, or this might push her away.

5. Do you put out on the first date?

Many of these are truly self-explanatory, such as this one. Coming on too strong would be an understatement. Maybe she did “put out” on a first date before, but she’s not going to “put out” for you after hearing that. Idiot!


6. What’s your bra size?

38 B, as in 38 NYB that is. For all who are unaware what that acronym means, it stands for “None of Your Business.” Unless she has just asked the size of your manhood, do NOT ask her what her bra size is. More than likely you have just insured you’ll never know the answer to that question, and instead, you’ve earned a slap in the face. P.S. Asking if “they are real,” is just as bad.

Say WHA???


7. When was the last time you had sex?

So many inappropriate/sarcastic answers come to mind to respond to such an inappropriate question. One being, “the last time your best friend had a day off.” Or “last year, I have a one year abstinence rule with whoever I date.” If a guy asks a girl this question on a first date, he is too immature to be seriously dating. Again, this question is none of your business. The girl will probably just walk off on you, because you’ve crushed the date. This will more than likely be due to the fact that she now thinks you are a pervert, or that you want to be with her for the wrong reasons.


8. How much money do you make?

Personally I’d be a smart-alack myself and answer with “none.” Then I’d follow it with asking him for the most expensive drink the place has (to put on his tab). Along with the most expensive meal if it’s a restaurant. I’d do that because the question is simply inappropriate. Asking a woman what she does for a living or where she works is fine. Following with the question of “how much money she makes” is too far. Are you wanting to latch onto her so she can take care of you? Are you looking for a “sugar momma?” Other than the fact you were inappropriate, she may start pondering these questions about you after such a remark.


9. Do you like threesomes?

Dude, unless she is extremely drunk, or is bi-sexual, you are not going to get a threesome. You have also just ruined your chances at a two-some. In the words of a popular modern song, “it will be just you and your hand tonight.”


10. Your friend is pretty hot isn’t she?

This is something you say to a really drunk girl at the bar. That may be the only way this would work for you dude. The last thing a girl wants to hear about on a first date is how attractive you find her friend. If your plan was to try to be greedy and get them both, you’ve definitely lost them both by saying this. Neither one would want you after this remark. Girls talk, especially best friends. If you treated one friend like this, then the other will assume you’d do the same to her. Plus, this is the number one way to ruin a friendship, by having two girls competing for the same guy. Ease down that ego and don’t think you are so special that you’ll have two girls competing for you. You will more than likely lose both, not to mention you’ll take a blow to your reputation, because believe me, girls will gossip and spread the word of their terrible experience with you.


11. Do you care that I’m married?

“No, no, that’s fine, why don’t you invite your wife on the date with us.” Are you kidding me? Is that the answer you were expecting? Of course she cares that you’re married, I hope she calls your wife right away and tells her what you are doing. I find it pathetic I even have to list this as a question. How stupid can you be? You would be surprised how many married men cheat on their wives it’s disgusting. Now, if hearing it on the first date is bad enough, some guys don’t reveal this information until later on in the relationship. He asks the question when you’re really starting to fall for the guy, or you’ve finally “given it up” which was his initial plan to begin with.


12. Do you like porn?

Seriously? Why would you ask that on a first date? Nothing is more romantic on a first date then going back to a guy’s apartment and watching porn together. I couldn’t be any more sarcastic. If a guy already needs porn and external toys or help in general to spice up his sex life on the first date...that’s showing a girl that she is going to have a very sad sex life with this guy. It should at least be a few months before the sex life gets boring and needs help to be spiced up. If you need to introduce porn on a first date to get the ball rolling, you have some serious issues dude. Now you can go home and watch porn all by yourself because you’ve just chased away your date.


13. Do you care if my best friend joins us? I love her like a sister nothing else, promise.

This one just may be the worst. Why would you want to bring another girl on your first date? It doesn’t even matter if she is your sister, the first date is supposed to be a time for a guy and a girl to spend alone time together to bond and get to know each other. This question is an instant deal-breaker. A woman does not want to share you with another woman she hasn’t even met on your first date together. Plus, this also comes off to a girl as your feelings are preoccupied elsewhere with someone else. She is going to feel jealous and uneasy about another girl already so close to you in your life, especially if the other woman is single. This would surely be my ultimate number one turn-off.


14. I think I love you, do you love me?

This is the first date you do not love her. If you think you do, you are immature and obviously too young to know what love is. The worst thing about this question is that it’s commonly misused by guys as a line to get girls to think they care about them. Many girls don’t want to make love until they are in love with the guy, and when they are also pretty certain the guy is genuine and so are his feelings for her. Guys play on girls feelings, and throw “the L word” out to make the girl feel secure with him, in the hopes that the girl will finally sleep with him. It’s a horrible but often used trick by men. Girls, use your judgment and don’t buy this crap on the first date.


15. Do you care if I “let one go?”

You are so not funny. That is a disgusting turn off. That is acceptable only after a long period of time being together with someone you care about. What’s next? Following the question with the pick-up-line, “My love for you is like diarrhea, I just can’t hold it in?” If you pass gas on a first date you can count on “blowing her away.”

I Want To Hear From My Readers

© 2013 Amber


eyeamnicegirl on February 12, 2017:

I've been asked if I was a virgin on a first date; I sort of understood where the question came from since I was only 19 and I met the guy at a Fellowship of Christian Athletes party. But still, talk about an awkward silence.

Amber (author) from Winston Salem, North Carolina on April 19, 2016:

Thank you to all my readers for the compliments and positive input regarding my article; I am glad you enjoyed it. I have many more fun ideas I will be posting soon, so if you liked this article, check out my other ones.

Nobody on May 04, 2015:

I think the worst is bra size

Johne243 on August 19, 2014:

Wow, this article is fastidious, my younger sister is analyzing these kinds of things, thus I am going to convey her. deagebddacgf

Anish Kumar from Mundi Kharar, Mohali, Chandigarh, (Punjab) on August 14, 2014:

Oh..a list of funny questions:).I hope no men would put these kinds of questions to any girl.LOL

Taiwo Kareem from Salford on July 11, 2014:

nice piece of article

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Kenneth Avery on May 01, 2014:

@ Kosmo,

Not so fast, my friend. (my Lee Corso impression). In my awkward dating days, I would have asked the question how much money do you make (so she could buy gas for my car), but not the are you wearing underwear or how many men have you been with, questions. That is just too personal.


Kelley Marks from Sacramento, California on May 01, 2014:

These questions are hilarious! Anyway, a thoughtful, perceptive person would never ask such questions on a first date - obviously, except in a sit-com like "Two and a Half Men." Later!

Mona Sabalones Gonzalez from Philippines on April 30, 2014:

This is a GREAT list. I was laughing from start to finish. Great hub.

Kenneth Avery on April 30, 2014:

@ TurtleDog,

Great line. Loved it. Or, "if we get busy tonight, would you care to dress up like Cinderella?"

If this keeps up, DATING will be an antiquated social event that WE helped to eliminate by instilling distrust in all single females.

TurtleDog on April 30, 2014:

Great list of the all time questions to never, ever ask on a date... Like "Hey, when's your daughter coming out? I'm supposed to meet her here" :-) Excellent post and great tips. Voted up and awesome

Kenneth Avery from Hamilton, Alabama on April 26, 2014:

I have been a member of HubPages for four years and read many, many hubs, but THIS ONE has to be THE Funniest by far, of all the hubs I have read.

I can see myself when I was dating, being so dumb as to ask questions like the money or weight thing, but not underwear or sexual partners for I was too embarrassed myself to bring that up.

Great writing.

Oh, how much money do you make?


arshiacom on December 08, 2013:

Some of the questions were really funny.most of all the 2nd and the 3rd one.

Hezekiah from Japan on December 08, 2013:

Most of the these are obvious but funny. Some people do say these things especially point No. 4 regarding the number of sexual partners.

vibesites from United States on December 06, 2013:

So outrageous! Hahahaha. My answer to those questions is mostly a smack across my date's face. lol.

cjarosz on December 05, 2013:

Wow. That's insane. I'm sure there are people who actually ask these questions.

Heather Baker from Florida on December 04, 2013:

I was going to respond to the poll but the bra size question wasn't there... unfortunately I suffer from an overabundance in the bra size department, it seems like I can't get past the first date without that question being tossed out there.

I come from Michi on November 26, 2013:

The list of horrific question's asked on a first date that you put together was creative and cleverly chosen. However, your remarks regarding each question was what made this article so entertaining.

ejparker from Fort Hood, Texas on November 25, 2013:

These are horribly hilarious. I pray no one has ever asked you these on a first date.

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