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10 Questions You Should Not Ask a Woman on a First Date

Updated on March 20, 2014
Ask the right date questions and love is yours.
Ask the right date questions and love is yours. | Source

The Art of Dating Conversation

If you're going to have any chance with women, be it casual, friendship, or sexual, you need to know how to avoid turning them off. Believe it or not, a simple conversation can turn a woman on and make her want you.

Women want a first date to be casual, free of pressure, and they want to leave wanting more.

Men want the same thing, but it's often the man who sends the date off on the wrong trajectory by disrupting the natural flow of conversation with lame questions. There's an art to conversation and men who don't understand that art usually destroy their chances with a woman in the first few minutes (sometimes even the first few seconds) of a date.

Are you one of those men? While you may need to practice your conversation skills regardless, it's always good to know some of the romance-killing questions you shouldn't ask if you want to last more than a few minutes with most women.

Are those your real boobs?

Asking a woman anything about her body is a bad idea just about anytime, but it's particularly bad if you're just meeting the woman for the first time. Any body question is an intimate one and if you're on a first date, you have no business asking any sort of intimate question. Asking an intimate question on a first date is a sign that you don't understand boundaries and people who don't understand boundaries are trouble in all sorts of ways. People who don't understand boundaries are wife beaters, rapists, murderers and such. Of course, not all people who have boundary issues are criminals, but the mere suggestion that you might have a problem will send most women running.

What's your favorite sexual position?

Sex is an inappropriate topic for first date conversation. Again, like the first question, this is an intimate question that indicates a boundary problem of whoever asks it. It's also extremely crass and presumptuous. It's also likely to make the woman extremely uncomfortable, which is exactly the opposite of what you want on a first date. In fact, here's a general rule of thumb: don't ask any question likely to make your date uncomfortable. The environment in which you ask such a question can actually make it worse. It's bad enough if you ask such a thing in a bar where, I suppose, there might actually be a situation where it's almost appropriate. However, ask it in a car or some other place where the woman feels trapped, and you're guaranteed to freak her out. As a rule, there should be no sex talk on a first date. There might be actual sex in some situations, but that should be the result of lots of hot, unspoken chemistry.

Dating frequency among men who...

ask stupid questions
remain silent
understand the art of conversation

What's with the stupid pictures of your dog?

Never insult a woman's dog, cat, or any other pet for that matter. Nothing will make a woman get up faster than telling her all those pictures she took with her dog make her look crazed. First of all, the dog is probably a substitute for a man because all the men she meets are dogs anyway. Her dog may very well be her best friend too. You might as well tell her that her mother is a whore.

Can you show me your...?

I can think of no noun that can follow the words "can you show me your" that make for a good conversation starter. Driver's license? Either you think I'm jail bait or you clearly think I'm older than I said I was or indicated I was in my profile. Underwear? You're a creep, plus maybe I don't wear underwear. Oh, so that's what you were trying to figure out. Tattoo? Well, that might be in a very private place. That's none of your business. "My best oh face?" Um, no. I'm not showing you anything. I just met you. Go get a clue.

Can we be friends?

You're on a date. You're not there to be friends. Men might not think that women know this, but we understand that when we say "let's be friends" it means that we don't ever want to sleep with you and that we don't think of you romantically. It's also another way of saying that there's no chemistry between us. Don't try to pull some reverse psychology garbage on us. We're the masters of that game, boy-o. And I didn't come out on a date with you to make friends just like you didn't.

Is it okay if I post a photo of you on my Facebook page?

That's creepy. So, let me get this straight. You want to post my photo on your Facebook page so all your friends can see us together? I just met you. We're not friends. Just like I don't sleep around, I don't let people post my photo all over the place either, but thanks for asking.

Can I kiss you?

If you think this is a legitimate question, you need to read my article on kissing, but suffice it to say, men who ask to kiss a woman are traveling a path of failure. If you're a man who's successful with women, you don't ask to kiss them, you just do it. That being said, there's a high chance that since we're on a first date, I'm not going to want to kiss you unless I'm sitting there melting while you're talking to me and you're Brad Pitt or that hunky dude from True Blood. Other than that, a hug is probably all I'm looking for if things are going well. Maybe I'm stuffy that way, but most women are like that. You'll know by the enthusiasm of my hug whether it's been a good date. You can try to kiss me on the second date if things keep going well.

Would you like to meet my mother?

The first question that comes into my mind if a guy asks me this is "do you live with your mother?" followed by "uh oh". Dude, this is a first date. We're not getting married. No matter how well a first date goes, I do not want to meet your mother during, after, or anytime soon. I don't want to meet your dad either. Or your brothers or sisters. Or your friends. Or your hamster. I'm just trying to figure out whether I even like meeting you so don't throw a wrench into the process.

You should not have asked me that question on our date.
You should not have asked me that question on our date. | Source

Do you like Gears of War?

Maybe I know what video game you're talking about and maybe I don't, but you might as well tell a woman that you spend all day on the couch, which incidentally, is not an attractive quality. When engaging in conversation on a first date, you want to be very careful about admitting to what kinds of things you like to do. Like if you like to beat baby seals, you might want to keep that to yourself. Try to talk about things that lots of people like to do and then expand on the topic slowly. Lots of people like to hike. Talk about that. If the woman says she likes hiking, then you can talk about what you like about hiking.

What's the lamest first date question ever?

See results

Do you think Obama is the Antichrist?

Politics is a bad subject for first date conversation. It's even worse if you're some kind of nutcase with an axe to grind. Whether it's on abortion (pro or con), gun control, tax reform, free markets - whatever your cause, just keep it to yourself. Rather than express your wacky political position, try to figure out what kinds of things the woman believes and once you determine she either agrees or disagrees with you, go from there. If you want to blurt out that you believe the President should be deported for one reason or another, that's probably going to be met with a look of concern, at the very least. All people are apt to like people more who agree with them.

© 2013 Sychophantastic


Submit a Comment

  • HaileyAdams profile image


    5 years ago

    LOL funny hub! A first date doesn't have to be like questanning, you can ask each other some general question but know when to stop.

    voted up.

  • Kris Bell profile image

    Kristen Bell 

    5 years ago from St. Louis, MO

    Hello there! Unfortunately, I have experienced variations of a few points you made on this list. Those guys did not get second dates. As comical as this Hub is it makes some good points, especially about intimacy and boundaries. Some lines should not be crossed on the first date. Shucks, some boundaries shouldn't even be looked at on the first date! Thanks for sharing! Upvoted :)

  • wildove5 profile image


    5 years ago from Cumberland, R.I.

    I can think of a few men I could show this too! Nice job!


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