Adolescent Sexuality, Courtship, Family, Learning, Love, Psychology, Relationships, Seduction, Sexuality

How to Ask a Woman for a Date?

Yesterday, I spoke with a fine young friend who lives in another state about the world’s most common near-death experience — also known as asking a woman for a date.

As you might expect, the conversation began casually enough with his desperately begging me to drive to Nebraska that evening and shoot him so he could avoid asking out a certain woman he works with.  Yet, shrewd, natural-born psychologist that I am, I sensed he might be beating around the bush.  So, I asked him, “Dan, I’m getting subtle vibes here — vibes that suggest to me you could possibly maybe just might be a bit troubled.  Is that correct?”

“Yes!  Please make it a head-shot.”

“Dan, I’m not going to shoot you….”

“Paul, you callous bastard, what have I ever done to you to deserve such a betrayal?”

A bit further down the sunny lane of our conversation, Dan finally admitted to the truth that I — with my sure-footed powers of insight into people’s very souls — had almost begun to suspect: He feels out of his comfort zone when asking women for dates.

It will astonish you to know that I utterly failed to put enough thought into what I said next: Out of sheer, unthinking sympathy, I immediately promised Dan I would write for him an informative post on how to ask a woman out.  He profusely thanked me.  And thanked me.  And thanked me.

That’s when I realized I’d committed myself to the deepest possible waters without an inflatable yellow duck ring.

As some of you might recall, I’ve chosen to remain celibate for the last 15 years or so.  And that’s my main excuse for having by now utterly forgotten everything I once knew about asking women out on dates.  So, although Dan doesn’t know it, yet, the total value of the advice I’m about to give him is — let us use a nice, polite word here — “modest”.

Poor Dan.

Unfortunately, a promise is a promise, and I have promised Dan that I will inflict on him a suffering greater than any he has ever imagined my advice.  So here it comes, Dan!  “An Honest Guide to Asking a Woman for a Date: May the Lord have mercy on you that you want Sunstone’s advice.”

To begin with…

To begin, Dan, let’s be brutally clear about the nature of advice.  Neither mine nor anyone else’s advice on how to ask a woman out is going to save you from ever experiencing defeat.  No mere words, no book, no lecture, no blog post can turn you into a pro.

Only practice can do that.

That’s because asking a woman out is fundamentally an activity, just like playing tennis is fundamentally an activity.  You can have the best tennis coach in the world, but that coach cannot save you from ever missing the ball, ever loosing a game. So, please give up any illusions you might have that the advice you are about to hear will turn you pro.  Only your commitment to practice, practice, practice will make you a pro.

I suspect you were not entirely happy to hear that, but it is the first and most important lesson you must learn.  Just as you cannot learn how to play tennis merely by thinking about tennis, you cannot learn how to successfully ask a woman out on a date just by thinking about how to do it.  You must get out there and try. Success is all about commitment to trying again and again until you perform at your best.

That was the bad news.  Now for some good news.  Through determined practice you can master the art of successfully asking women for a date.  I did it — I was once very successful at it — and you too can be frightened into celibacy by the weird women you’ve managed to date can succeed beyond anything you currently imagine is your doom possible for you.

Why you should be scared, Dan.  Very scared.

Correct me if I’m wrong, Dan, but during our conversation yesterday I somehow got the impression you feel out of your comfort zone when asking women on a date.  Of course, that’s because you’re scared.  So, it stands to reason that if you can get beyond your fear, you will find yourself smack-dab in your comfort zone.  And that would be a good thing.  Right?

So, let’s focus on fear.  It seems to me there are at least four possible causes of your fear.  First, I’ll list those four causes and then tell you how to deal with each of them.  In the end,  I assure you that you will have gone beyond mere fear and reached the sublime state known as “terror”, for by then you will have realized that terror is the only appropriate response to receiving advice from me.  Here, then,  are my guesses about why you might fear asking a woman for a date:

  • You do not believe in yourself and/or your motives in asking her for a date.
  • You sense on some level of your being that you and her are basically incompatible.
  • You are uncertain how to go about asking her for a date.
  • You fear rejection.

Let’s now blithely discuss each of those common fears in turn.

You do not believe in yourself and/or your motives in asking her for a date.

It’s quite common for folks to not believe in themselves. Even many successful folks or outwardly confident folks do not believe in themselves.   But unless you are really, really foolish — so foolish, in fact, that you would do something as foolish as take the advice of a 51 year old celibate male — in other words, laughably foolish — you have nothing to worry about, Dan.

I hope I have reassured you.

Here’s the work-around for this source of fear:  Begin by asking yourself, “Why would she want to go out with me?”  Now, if you are like most people who suffer from not believing in themselves, you will immediately start thinking of all your flaws.  You will say things to yourself like, “Why would she want to go out with me?  After all, I am poor.”  Or, “After all, I am fat.”  Or, “After all, I am ugly.” Or, “After all, I am known to listen to the advice of a 51 year old celibate male.”  That’s the sort of mind-garbage with which most folks who do not believe in themselves answer the question.  All it does is heighten your fears.

The correct answer to, “Why would she want to go out with me?”, is another question, “What can I offer her that she will really want to do?”  In other words, do not think so much of yourself as think of her — her desires, her needs, her wishes, her tastes.  Those things vary from woman to woman even more than do shades of nail polish, so it’s a very good idea to ask her, rather than guess.

As often as possible, I used to do that sort of asking far in advance of actually asking a woman out.   Say, a month or so before I would inflict the “big question” on her, I would very casually begin asking her about herself, what kind of hobbies she had, what she did for fun, and so forth.  “Do you have any hobbies, Marie?” “Why yes!  I’m a serial killer, Dan.”  You see how easy that was?  Good.

Once you have an excellent idea what sort of things she finds attractive, you should figure out what would be a fun date for her.   That might be pretty standard fare — such as dinner and a movie.  Or it might be something like rock climbing.  But tailor it to her.  If you are going to ask her to dinner and a movie, know in advance which cuisines she likes and what kind of movies she likes.  Don’t go generic with women.  Ever.

Are you following this, Dan?  Dan!  Wake up!

Do you see what’s happening here?  If it’s true that a source of your fear is you do not believe in yourself and/or your motives for asking her out, you can work around that mess by focusing on what she would like to do.  Let her happiness mean more to you than your fears.

You sense on some level of your being that you and her are basically incompatible.

Now ask yourself, Dan, if you are compatible with her.  Basically, fundamentally compatible.  It’s a hard question to answer, but you need to bring it up with yourself.  How well do you get along with her? If you don’t know the answer to that question, then you have not spent enough prep time with the object of your wanton desires to be asking her out yet.  So, go back and spend more time just getting to know her first.

On the other hand, if asking that question reveals the two of you are basically incompatible, then make plans to find someone else to ask out — but not her.  By the way, that might seem like simple advice, but you would be surprised how many people don’t think to take it.  They date people they are fundamentally incompatible with, they marry people they are fundamentally incompatible with, and — then they divorce people they are fundamentally incompatible with.

You are uncertain how to go about asking her for a date.

This is a question of technique, of course.  Americans are big on technique, Dan.  Or have you not noticed that most of the advice you have seen on how to ask a woman for a date has focused on what technique to use?  Since there is so much advice already out there on specific techniques, I am not going to concentrate much on what words to say, etc.  You can find more (and better) suggestions about that elsewhere.

Instead, I will simply say this: Since you have told me you are very scared about asking a woman out, adopt a technique that will reduce or ameliorate those fears, rather than attempt one which will heighten your fears by requiring some great art or skill to pull off.   Don’t think technique is so important that you must flawlessly execute some pick up line that is absolutely fabulous and mind-blowing.  That’s nonsense.  Most of my dates came from very simple lines like, “We should go see it together!”

The key is to be casual and take it easy.  Don’t ask one big question, such as “Would you like to go out Friday night?”  Instead, ask a series of little questions.  Get her feedback as you go.  If she stops answering affirmatively, then you can easily back out without too much embarrassment.  For instance:

“Hey, Marie! Didn’t you tell me once that your hobby was streaking monasteries and convents?”

“Sure, Dan.  What’s up?”

“Well, I heard the brothers over at St. Francis De Assisi are holding a special mass for children orphaned by rabid mice Friday night — have you heard of it?”

“No. Really?”

“Really! I’ve been planning to streak the brothers forever!  This is a dream come true!  You should go yourself!”

“Well… maybe I will.”

“Good!  It would be cool if you can make it!”

Notice how in the above conversation you suavely match her level of commitment with yours, Dan.  When she responds to your subtle request (i.e. “You should go yourself”) with a non-committal reply (“Well… maybe I will”), you respond with an equally non-committal reply (Good! It would be cool if you can make it!”).

In the little dance men and women do when courting — and asking a woman for a date is the start of formal courtship — you should lead your partner one small step at a time.  If she responds affirmatively, then take another small step forward.  If she responds in a non-committal manner, then match her non-commitment.  And if she backs off, then back off with her.  In other words, don’t drag her around the courtship floor — dance with her instead! Now, let’s pick up the dance where we left off:

“Good!  It would be cool if you can make it!”

“Actually, I’d love to go, Dan, but I don’t have any way of getting there.  My car will be in the shop having a cow catcher installed on it that day.”

“Wow!  You’ve been hitting cows, Marie?”

“Children, Dan.  They’ve been messing up my grill.”

“Oh, how awful of the negligent brats!  Well, I can give you a ride.  And it would please me very much if you would accept.”

“Thank you, Dan!  Well, since you put it that way, I will.  After all, I aim to please!”

“Fine.  The mass is at seven-thirty.  Say, how about we get together for supper at six!  We can try out that new Italian restaurant you were talking about last week.”

“Oh, that would be great, Dan!  What time can you pick me up?”

Dan, do you see here how you make it a dance?  Don’t think technique is so important you must flawlessly execute it.  Much more important than any technique is you’ve done your homework, know the two of you are compatible, and know what sort of date or activity will make her happy.  Asking for a date is in some ways remarkably similar to making love — it should 80% about her, and only 20% about you.

You fear rejection.

It’s finally time to be honest with you, Dan.  I can’t help you much here. There are several proven, but very specific ways to overcome the fear of rejection.  Some might work for you, but some will only work for someone else.  Before I could with confidence recommend a specific technique that’s best for you, I would need to give you a couple standardized psychological tests and know more about you as a person.  I don’t have the space to do that here, so I’m not even going to try.  Instead, I’m going to give you a worthless pep talk.

I’m pushing 52 years old now, and when I look back on my life, I realize I do not regret the many times some woman has said, “No” to me.  Instead, I regret the times I did not ask one or another woman out because I was afraid she would reject me.    You see, I started out being just as scared as you are.  It was only through repeated trial and error — and sometimes the help of others — that I learned how to work around my fears, get pass them, and successfully ask women out.

The moral is: You can do the same.  You can successfully ask out tons of women — but you must be to willing to learn how.  And that means practice, practice, practice.  So, beyond all else, make a commitment to learning how to play the game, how to dance the dance, how to ask the babes out.  That’s the single most important thing you can do.

I hope all this has helped.  I am now going to ask anyone who has read this to chime in with their own advice for you.  Maybe we can get a thread going here that’s full of good, sound advice and help.

Anyone want to pitch in and help Dan here?

21 thoughts on “How to Ask a Woman for a Date?”

  1. Stop worrying about what you’re feeling. That’s not the issue. It’s what you’re not doing that’s causing pain. It’s behavioral, not cognitive. Do it. You’ll feel better and it’ll be easier next time. You won’t die.


  2. From the other side of the pond and the gender divide, I’d say, try not to wait so long between deciding you want to ask and actually asking that it becomes a major stress to you.

    I think the longer the wait, the harder it becomes to come across as “if you refuse we’ll miss out on doing something fun together”. Over time it seems to turn into “if you refuse I’ll be heartbroken because I’ve been brooding about the perfect way to do this for weeks, oh, and stalking you to find out your preferences a la groundhog day too”. Trust me, creepy isn’t good!


  3. Thank you all. And Lirone, I feel like I’m all most there. I have been putting this off to long. If I start to get creepy, I’ll just back off…. ^_^


  4. I asked a woman out once a few years back; next month I’m gonna open the curtains. The week after that I’m gonna try make it all the way out to the mailbox.

    Kidding, just kidding.

    Just be yourself, mate – be chivalrous be respectful, and be honest.


  5. Interesting, very interesting. Would never have imagined that there was so much involved in the simple act of asking a woman out.
    Couple of questions: Do women ever take the initiative and ask a man out? is it acceptable?
    And in such a case is it ok for a man to back out with an excuse?
    Thanks for the delightful post Paul. Got up feeling rather dull and now I am smiling from ear to ear.


  6. Hi Usha! You’d be surprised how many big, strong men are more terrified to ask a woman out than they are to walk backwards in traffic. I can recall talking about it in all night college bull sessions and many guys were mortified by the prospect of rejection.

    Do women ever take the initiative? It only happened once or twice with me, but I suppose it might be more common nowadays. Back when I was dating, women would more typically do everything just short of actually asking a guy out. That is, they’d do almost anything to let you know they wanted to be asked out. But I guess the unspoken rule back then was the guy still had to do the actually asking.

    I do know that it’s technically acceptable today for a woman to ask a man out, but that might be the ideal more than the practice. I’m not really sure how often girls ask guys out nowadays compared to guys ask girls out.

    By the way, that’s different when the relationship is “just friends”. My female friends ask me out all the time on a “just friends” basis.

    You’ve raised some fascinating questions. I wish I had more definite answers.


  7. Paul, I am glad you mentioned the ‘just friends’ type of going out.
    I wondered if all the fuss about asking a woman out was because the man wanted something more out of it than pleasant company and conversation. It is perhaps treated like some kind of an investment decision? or is it because one is already considering the possibility of taking it beyond the zone of just friends?
    And you did not answer my q about if it is ok for a man to back out or is it considered ummanly behaviour?


  8. Those are excellent questions, Usha! If there’s one reason more important than any other for all the fuss some guys make about asking a woman out, then surely it must be fear of rejection.

    I strongly suspect that fear of rejection is intensified by any sexual feelings the guy has for the girl. If he’s thinking, “I hope this leads to something — either now or later”, then he might be prone to see her “No, I don’t want to go out with you”, as a rejection of him on more than one level. So, yes, wanting something more than pleasant company and conversation is, in my opinion, most likely going to intensify any fear that’s there.

    A friend of mine was telling me just two days ago how she was in her 30s before she understood how fragile men can be when it comes to being rejected by a woman. The way she put it, before her revelation, she thought we had egos made of steel. That is so not true of many — probably most — men. And some men are close to terrified of rejection by a woman. Either that is true, or I have been lied to many times in my life by men who’ve confessed their fears to me. I can relate to those fears because when I was young I shared them to a great extent. I can remember being devastated that this or that girl would not go out with me in high school.

    It’s my understanding that it’s becoming increasingly common for young people today in America to go out in mixed gender groups, rather than go on couple dates. I would have to read up on that, though, and see what’s being done on the coasts because my poor town is far from being the trendiest place in the country.

    I very much suspect dating habits in America vary from location to location and by the age of the people involved. My hunch is group dates are more common with kids and couple dates are the standard for adults. But I’m no real authority on current trends. We celibate 51 year olds are the last to know what’s going on!

    Yet, I’m certain it is ok for a man to make excuses instead of accepting a date with a woman who asks him out. Sorry I forgot to mention that earlier.


  9. Thank you Paul for taking the time to enlighten me on this.
    The topic itself as you might have guessed by now is only of academic interest to me – somewhat like reading up on the mating dances of birds. But it is truly fascinating.


  10. @ Thomas: Spot on! That’s good advice, and well said. Welcome to the blog!

    @ Shefaly: That was the most disgusting attempt to ask a woman out I’ve ever heard of! Thanks for sharing that! Dimitri redefined “looser” there.

    @ Lirone: Thank you so much for pointing out how all this can be overdone! I think it is often important, though, to know a woman well enough that she’s comfortable with you before asking her out — that has always worked best for me.

    @ Dan: You see the power of blogging? Now, from the commentators, you are getting some real help!

    @ Scotty: Good advice!


  11. Usha: It is indeed fascinating, isn’t it? Of course, humans would not be social animals and live in cities together if were not fascinated with what each other does.


  12. yuch. dimitri’s arrogance is, unfortunately, all too familiar.

    i’m out of the game now, but i’ve asked men out countless times and i’ve learned how to handle rejection well. mostly i eased into it, like paul suggests, out of a common interest, on friendly terms, and that’s the approach from men i’ve always been comfortable with — and how my present relationship started.

    i never liked getting asked out for the purpose of initiating a romantic relationship. it was too stressful and felt artificial.

    i do wonder why i don’t find asking somone out as gut-wrenching as many seem to — and i suspect that it’s because i don’t believe in a soul-mate. the response won’t make or break me.


  13. For me dating and sex are areas where gender equality and taking similar roles just doesn’t work. There are too many drives and deeply programmed reactions that are completely different between the sexes.

    So while I have absolutely no problem asking male friends out, and would be willing to ask potential mates out as well, I find men actually like to feel they’re hunting and seducing! Put another way, asking may be agonising, but

    Reliable contraception and economic independence mean that the stakes in the mating game are in practice completely different for women. But humans do seem to be fairly hard wired to the rather different situation in which our mating drives evolved. It’s probably rather unfair that this often gives women the best of both worlds…


  14. Paul,
    This was an excellent idea for a blog! What a creative way to give advice to a friend far away and capitalize on the collective knowlege of those of us out here in cyberspace reading your posts.

    To Dan I’d like to say, consider this: nothing ventured nothing gained. Most women, if they do reject you, will do so graciously. Also, a first rejection is not always really a rejection. It could be she really did have plans that she cannot change without letting others down and yet she’d still like to go out with you but she may not know or be able to express this well during the conversation. And, I also have heard that some women can be ruthless and dehumanizing when rejecting a man’s overtures. I find this appalling and I hope it never happens to you, but if it does, then you’ve learned something about her character haven’t you? It is painful if/when that happens, but it isn’t a total loss either. You learn something positive from every interaction…so…take Nike’s advice and “Just Do It!”
    Best to you!


I'd love to hear from you. Comments make my day.

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s