I spent many years as a counselor in the field of mental
health, but I also worked as a salesman for a compatability
dating service, and learned a lot about relationships and
dating in the process, from a variety of perspectives.
As a recovering salesman, I'll (unfortunately) never forget the
first rule of salesmanship: "sell the sizzle, not the steak",
which means to sell the benefits of the features of a product,
instead of just pointing out the features, and leaving the
customer to figure out the personal benefits for themselves.
In the case of a date, asking someone if they want to go out
with you provides only a vague image of being with you in the
midst of some foggy environment, which places their attention
on you and the vague sense of interacting with you in some
undefined fashion. This is more likely to make someone feel
nervous and on-the-spot, leaving it up to them to imagine
positive circumstances and a positive outcome. They are
unlikely to achieve this unless they've already been having
This can be modified with much better results, I believe, by
your knowledge of their interests, and you can choose which
of their interests will allow for the level of intimacy you
wish to experience during the date, even outlining a scenario
of several experiences which will lead to increased intimacy
as the evening progresses.
To accomplish this easily, you can wait until she mentions
an interest which she is already excited about, be it a
movie or the shark exhibit at the city aquarium that she
heard about from a friend. Then simply build on that and
suggest something like, "Sayyy, I've heard about that too.
Why don't you and I go there together! Then afterwards,
we could go to this restaurant I've been meaning to try
and have a nice, quiet dinner. We can talk about our
experience and get to know each other a little better,
which I would really enjoy." Then talk about the kind of
food available at the restaurant, and negotiate from
there, offering the possibility of going to a different
restaurant, such as one of her favorites, if that would
make her happier.
That way, you're building on something she's already
excited about, instead of some foggy image of hanging
out with you. You're inviting her to do something she
already enjoys and offering her the prospect of sharing
the experience with someone she already knows, and can
get to know better by the sharing. And you're offering
yourself the same thing.
In my experience, this is what women really want from
a date anyway. They don't just want to focus on you,
and on what might develop from that. They want to
focus on sharing an activity and getting to know you
in the process, which can lead to greater intimacy in
ensuing activities if there's some chemistry there.
It's the often cited "friends first and we'll see
what develops from there" concept.
The other concept from sales which comes to mind here
is that the second question, "Do you want tea or coffee?",
isn't a yes or no question, as is, "Do you want to go
out with me?". Sales people recognize the advantage of
asking questions that don't have yes or no answers.
A "no" can end the negotiation very quickly. A question
that doesn't have a yes or no answer is called presumptive,
in that is presumes that the answer is, "Yes, I want a
hot drink, and I'd prefer the coffee, thanks".
You can fit this into your strategy for asking for a date
by, again, letting her take the lead in telling you about
things she's interested in. Perhaps she mentions a movie
she'd like to see, in addition to the aquarium exhibit
she wants to take in. You can then phrase your question
along the lines of, "Both that movie and the aquarium
exhibit sound like things I'd also enjoy. I have some
free time tomorrow, and I'd really enjoy doing one of
those things with you. Would you rather go see that movie
or go to that aquarium exhibit with me? Once she picks
one, negotiate having dinner afterwards, as above, or
toss in the idea quickly, before she answers, to sweeten
If you don't yet know her well enough to have the kind
of conversation that will lead her to disclose the sort
of activities she finds enjoyable or interesting, I'd
encourage you to work up to that level as an interested
friend, first, perhaps by getting her phone number and
having some friendly conversations first.
Some of the same suggestions, as well as others, such
as smiling when you ask, practicing what you're going
to say, and so on, can be found in the following
'Ask a Girl Out on a Date', by Nathalie Lussier:
'Asking Someone Out', on the crush.com website:
'How to Ask a Woman Out', by Jason Lindholm:
'How to Ask a Woman Out', by Edward Raver:
'The Best Way to Ask Single Women Out on a Date' by
Don Diebel ("Americas #1 Singles Expert"):
Don Diebel's website:
There's much more advice out there, but I've tried to
taylor my responses to the specific situation you've
described. If you have any questions, please request
an Answer Clarification before rating this answer.
Additional information may be found from further exploration
of the links provided above, as well as those resulting from
the Google searches outlined below.
Searches done, via Google:
asking a girl out
asking a ~woman out
Clarification of Answer by
22 Oct 2006 12:08 PDT
Thanks for your feedback and clarification. I'm not sure that
additional examples will work as well to eliminate your sense
of discomfort with asking this type of question as will a
better understanding of this approach.
First of all, you're right to ask for ways in which you can
feel more comfortable in utilizing a presumptive question,
because how you feel when asking the question will certainly
influence how she feels when asked it.
And you would be quite correct to feel shy about using this
presumptive technique if that's all it is to you. Many a
salesman has sunk to using this as a sales-closing technique
designed to do little more than box in the customer in a way
that SHOULD make the salesman uncomfortable, because they're
trying to force an outcome for which the desire has not been
established. This can be seen in situations where the customer
has acknowledged some of the benefits of the product, and the
salesman then tries to corner them into a purchase by asking,
"So would you like to pay for that with cash or credit?"
The problem is that, though the customer did acknowledge some
benefits of owning the product, they didn't yet say, "I want
This is why I'm encouraging you to spend the time to get to
know your intended date well enough to actually perceive a
high level of excitement when she talks about the movie or
the aquarium, or whatever it is that truly interests her.
By doing so, you are avoiding the pitfalls of manipulative
sales people, because she has already expressed an intention
to participate in those activities. The more certain you can
be of this before you ask her out, the better.
Then you're not boxing her in with your offer to choose one
or the other. Instead, you're offering her two paths which
she's already expressed interest in following. Additionally,
you're offering her the chance to be accompanied on either
(or both, if things work out) of those paths. And very few
people would rather engage in a public activity alone when
they could experience it in the company of someone they know,
and would like to know better.
Again, you're essentially offering yourself the same thing
you're offering her, so the more truly excited the both of
you are about the activities you're suggesting, the better.
What reason have you to be shy about suggesting something
which will be so fulfilling to the both of you? What reason
is there to be nervous about expanding your, and her, horizons
in such a beneficial way?
In summary, both you and she will only be uncomfortable to
the extent that you or she perceive(s) that you are trying
to manipulate her (and yourself) into a situation that she
(or you) may not really find enjoyable. Therefore, be clear
and honest in your own perceptions. Make sure you are really
offering her the opportunity to participate in activities
that truly interest her, and that they are things you would
enjoy experiencing, as well. Build on the actual enthusiasm
and excitement that arise in talking about these activities.
Then be honest in admitting your interest in pursuing them
along with her.
The only question you're really asking is whether she can
conceive of enjoying these activities with YOU. So, again
minimize that detail and focus her attention and emotions
on the activities themselves. Then you can even phrase the
question in such a way that you present the advantage of
going together as being beneficial for you, in a way that
suggests it will be equally beneficial for her:
"I'd really enjoy going to both that movie and to see the
shark exhibit, but I'd much rather go with someone I know
than go there by myself. Half the fun is being able to
talk about it afterward with someone who was there with you.
If you would give me the pleasure of accompanying me, which
would you rather do [first]?"
You can end with "...which would you rather do?" if you're
not feeling very confident, or you can end with "...which
would you rather do first?" if you're very confident that
you're likely to receive a positive answer. That tells her
that you're interested in seeing her more than once, and
sets the stage for a series of dates.
In either case, you've buried the question of whether
she will accompany you by making it a compliment with
the implication that "your accompanying me would give
me pleasure". You're presuming that she'd like to do so
and focusing the question on which activity she'd rather
I hope that helps!