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15 Questions Men Don’t Want Women to Ask on a First Date!

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Oftentimes I have read articles about women that state they have had more first dates than they can count. Very rarely do these women get asked out for a second date and almost never get asked out on a third date. Too often the problem is these women are trying to put the cart before the horse. Instead of approaching the first date with the intention of just having some lighthearted fun they behave like a woman on a mission.

The first date should be all about having fun! You want to see if there is any chemistry between you. Asking the wrong questions or the right questions at the wrong time can kill your chances of getting a second date. Below are 15 questions that could zap the fun out of any first date.

Where do you see yourself in 5 years?

In all honesty it doesn’t matter much what a person’s plans are for the next five years if you don’t enjoy their company on the first date. The purpose of a first date is to see if we have chemistry. Odds are if we don’t there won’t be a second date. Let’s just see how tonight goes!

Have you ever been in love?

This question in and of itself is not a bad question. The problem is it opens the door to an avalanche of other questions. If he says (yes) or (no) there are bound to be follow up questions. Talking about the past too early takes away from enjoying the present.

How many times have you been in love?

Whether someone has been in love once, twice, several times, or not at all has nothing to do with you being asked out for a second date. Falling in love involves so many things coming together. Just because someone has been in love in the past does not mean they will fall in love with (you). It’s also worthy to note if someone has never been in love it doesn’t mean they won’t fall in love with (you).

Why did your last relationship fail?

No man wants to talk about failures and mistakes on a first date! In fact anyone that starts a (first date) off by telling you all about their ex has probably not gotten over their ex.

What have you learned about yourself from your past relationships?

Once again this question deals with failure. Each of us (chooses) our own friends, lovers, and spouse. The number one reason for any breakup or divorce always comes down to (selecting) the wrong mate for ourselves. He has not found “the one”. Clearly if he had he wouldn’t be on a date with you.

Have you ever been cheated on?

Nothing like having flashbacks of betrayal and heartache to put a guy in a romantic mood! If his answer is (no) he now has concerns about you. There really is no upside to this question.

Have you ever cheated on someone?

If a man answers (no) most women won’t believe him and if he answers (yes) most women will assume “once a cheater always a cheater.” They could care less if he is 35 years old and the cheating took place when he was 17 years old. Many in our society believe it is possible to be a former smoker, drinker, or drug user but when it comes to cheating, that is something no one can stop doing!

In reality the smoker, drinker, and drug user mostly hurt them self. Cheating hurts us. This explains why we put cheaters in a “box”. It simplifies things for us by having a hard fast rule of not taking a chance. Intellectually and logically it makes no sense to believe once someone does something they are stuck doing it for the rest of their lives.

What qualities would you want in a wife?

Slow your roll! It’s just lunch, a movie, an event of some kind. Even if he’s “wife shopping” he is not going to tell you how to behave in order to get him to propose. Be yourself and let the chips fall where they may.

How many children would you like to have?

As rewarding as being a parent can be most men are aware once children arrive sexual passion takes a major hit. The “infatuation phase” of a new relationship is about enjoying each other and having the freedom to be spontaneous. Discussions about having children and the responsibilities that come with that change the image he has of you from beautiful goddess to matron. Quite often once a woman becomes a mother she has less interest in being a wife. Not many men are in a rush to drop down the priority list especially on a first date.

How is your relationship with your mother?

Men either are attracted to women that have the same traits and values of their mother or they want a woman who is the complete opposite. However talking about mom on a first date is a romance killer!

What is the longest period you’ve ever dated a woman without having sex?

Are we shooting for a new record? Seriously this notion that the longer a woman “makes a man wait” for sex the more he will respect her is not always the case. Not all men are alike. Some men may wait six months to have sex with a woman while having sex with other women. Each of us is entitled to have our own “dating rules”. You should only have sex when you think it’s the right time for you. Whether the man has a “3 date rule” or he wants to wait until he is married to have sex, it should have no bearing on what (you) want to do with (your) body. This is a pointless question. If a man wants to have sex with you he will make a move on you. If he does not want to have sex he will not. Either way discussions about sex lead to thoughts about sex. Trying to set a man’s expectations before he shows interest in you that way is a turn off. Most men would rather read your body language and interpret the tone of the conversation (sexual innuendo, flirty responses or absence thereof) as opposed to being told.

Why is it you never got married?

This is one of those questions many women hate to be asked and yet they have no problem asking a man. The assumption is a man that is 35 or older who has never been married either has something wrong with him or he does not want to be married. In essence it’s not because he has not met “the one”. It’s because he is a jerk or trying to be a player. There has to be (something) wrong with him. You may as well have asked him, “What is your problem dude?”

Are you afraid of commitment?

Being a man all of my life and having had male friends I have never ever heard a guy proclaim he was “afraid” of commitment. There are over 2 million weddings that take place in the U.S. each year and the lion share of those weddings occurs after a (man) proposes to a woman. Not only do we have a divorce rate hovering over 50% a recent study indicated that (women) initiate 66% or 2/3rds of all divorces in America! After hearing nightmare stories of men stuck with expensive child support and alimony payments, moving out of houses into studio apartments it could be argued that men are afraid of divorce! Using words like “afraid” or terms like “a real man” are seen as manipulation tools used by women to get men to do what they want them to do. Coming across as a manipulator is not a good thing.

What would you say to a woman that accidentally became pregnant with your child?

End of date! Check please! Seriously? I can’t imagine what date number this question would come up. It is definitely not something that should be asked on a first date! Whether a man is pro-life or pro-choice he can’t force a woman to have an abortion nor can he force her to give birth to his child. The laws are fairly clear that only the woman has the power to determine whether there will be a birth or not. If you’re fishing to see if he wants children refer back to question number 9.

If I called your ex-girlfriends what would they tell me about you?

“He’s the one I let getaway. I threw away a winning lottery ticket!” Come on! What type of response would you expect from a man to a question like this?

Questions you might ask on a first date

What led you to ask me out? What do you enjoy doing for fun? If you could visit any place in the world where would you like to go? What is your favorite type of food? Who is your all-time favorite singer/band? What is the funniest thing you ever heard or saw? Even with these questions you don’t want to ask them in “rapid fire” style. Let him ask you questions too.

First date questions should be “ice breakers” and encourage the other person to relax. Dating should be a fun exploratory process. Your attitude affects your altitude. Stop trying to create instant “serious relationships” and learn to allow casual dating to “evolve” into something serious if the feelings are mutual.


Written by

Kevin Darné is the author of My Cat Won't Bark! (A Relationship Epiphany). The book is about learning how to approach relationships with complete awareness, having realistic expectations, and using self-empowerment techniques. Kevin is also a Chicago Dating Advice Examiner for where he publishes articles offering advice in the tricky world of dating. In addition he is also a Continuing Education Instructor for School District 211 located in the NW Suburbs of Chicago where he teaches classes on "How to Find and Choose Your Ideal Mate" and "Avoid the Catfish! How to Date Online Successfully! Kevin is a frequent guest of radio and TV talk shows. You may follow Kevin on Twitter. @kdarnelovealert

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