Pickup Question Guide

Questions to spice up your

conversations with women

Eddie Hitchens
Maciek Drahusz

1 Pickup Question Guide

Intro
There is one question that we at Street Attraction get asked over and over again ''What do I talk about
with a girl?'' The average man usually doesn’t know how to engage a women on mutually interesting
topics of conversation. We've all been there, during a pickup or date the nerves kick in and we go into
a robotic mode of asking mundane questions.

This guide lists some of the more interesting questions to help you engage a woman in order to
develop the relationship further. Make intelligent use of the advice in this guide at the appropriate
time in the interaction and you will be light years ahead of most other men. Don't be afraid to
experiment and come up with your own material once you get the hang of the underlying principles
behind these questions, unlike many other dating companies we are not interested in turning you into
a pickup clone!

Don’t bombard a woman with one question after another; you’ll make her feel like she's in a job
interview. Ultimately the questions are just a means to spark an engaging conversation that is fun and
playful and later deep and seductive. Read these questions, keep a few in your mind or store them on
your mobile phone, and perhaps use this list when the conversation starts to run dry. Avoid asking her
too many questions, often just asking two or three good questions during the conversation will spice
things up and get her to open up. Be very careful not to ask more than two questions in a row without
making statements (especially early on in the pickup) as you risk the ‘interview mode’ mentioned
earlier which will end up killing the conversation and attraction.

Good conversation is not just about asking questions, no matter how good they might be. A charismatic
conversationalist and seducer blends questions and statements to create a compelling and balanced
conversational mix. A simple rule to follow is:

Make a statement then follow it up with an evoking question (usually related to her), for example;

Her: “I love cats”

You: “Cats are cool, I like how gracefully they move about and their 'I don't
give a fuck' independent spirit and attitude. Tell me, what is it about cats
that you love?”

Your statement and question should give her enough material to get her talking. There are few
important things that you should be mindful of when in conversation:

»» Good body language: Sit up straight or stand tall, with your hands open and arms and
legs uncrossed. Open and expanded body language conveys confidence but also helps
her to feel more relaxed when talking with you.
»» When listening, slowly nod from time to time and make the occasional encouraging
sound and gestures.
»» Solid eye contact: Make sure to look her in the eyes when you're talking, it's okay to break
it occasionally. Break eye contact mostly when she's talking and you're listening. Never
break eye contact by looking down, it's a sign of submission, instead break eye contact
by looking to the side. Give her plenty of eye contact by be careful not to make her feel
uncomfortable.

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 »» Keep it light (most of the time). You can obviously talk about serious subjects now and
again, but focus on playful and light hearted topics of conversation to distinguish yourself
from boring serious office drones.
»» Use humour: however don't feel the need to be funny all the time, you don't need to be
her clown.
»» Lead the conversation: Don't monopolise it, but bring in new topics from time to time,
rather than letting her run the entire conversation. If your date isn't moving towards your
intended goal, consider changing the topic/s.
»» Don’t seek her approval: Women love a guy who is prepared to challenge them, it
demonstrates high value and is a sign of masculine dominance. If you seem like you're
trying to please her all the time, she’ll quickly lose interest in you. If you have opinions
that are different, don't be afraid to voice them (but don't start an argument or a long
debate).
»» Don't be afraid to talk about the things that you like or enjoy. If you love drag racing,
world war two documentaries or rare Ethiopian jazz vinyl records mention them in
the conversation. Let her know why you're passionate about it, they key is to talk with
enthusiasm. Enthusiasm and passion are qualities that women find attractive in a man.

The question game

The premise of the Questions Game is simple. If you're on a date or just hanging out with a girl and
the conversation runs dry or you're not really sure what else to say, you can suggest playing a game
called "10 Questions" where you take it in turns to ask each other a question at a time. You each have
to answer the question asked. It's a simple game, but usually very effective at sparking interesting
conversations.

You: "Okay we're going to play the 10 Questions Game.." (vary the number
of questions according to the time you have to fill)

This sentence will usually re-engage her. Explain the premise of the game to her and fire off your first
question, for example;

You; "Ok I'll start, what's your favourite album to listen to when you want to
get into a good mood?"

Make sure that the first few questions you ask her are non sexual. Spice it up and get more sexual by
the 4th or 5th question.

Playing this game will usually reignite the interaction and will often lead to very interesting and sexy
conversations. The beauty of this game is that it's so simple. When she gives you her answer, it gives
you an opportunity to take the conversation off on a tangent, then when it runs dry you can then go
straight back to the next question. If there's any chemistry between you and her the game will help
you fast track the sexual escalation, so you will rarely ever make it to question 10.

3 Pickup Question Guide

Questions Not To Ask
Before reading what you can ask it's best firt in, things that can offend her badly or make you
to think what to avoid. We have listed some look bad. Some questions are just boring; others
common questions that guys often ask which will just make you look unattractive or even
should not be used. The general rule is not to ask scary. The following questions are conversation
her things that you are not genuinely interested killers and attraction destroyers;

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How much do you weigh?

There's no point asking her how much she weights, if you found her attractive
enough to approach, then her weight shouldn't matter. Asking such a question will
often make the woman feel self-conscious. Also most women will find it rude for
you asking.

When was the last time you were cheated on?

Don’t ask girls about negative stories from their previous relationships. Also don’t
talk about how your ex cheated on you or how you cheated on her. Even if you had
bad experiences, avoid moaning or bitching about your ex-girlfriends, it makes you
look weak and pathetic.

When was the last time you had drunken sex?

Drunken sex isn’t romantic and usually is seen as a mistake by women. This could
imply that you think the girl you are with is a slut who will fuck anyone who gets
her drunk. Avoid suggesting that she is slutty even if it’s apparent. When talking
about past sexual encounters, mention positive and adventurous experiences.

Who is your best friend?

It’s better to avoid talking about her friends too much. It’s an easy way to the
friend zone. You are not trying to become her friend but her lover, besides why do
you care who her best friend is.

Can I kiss you? Would you like to come to my place?

Asking girls if you can kiss them will almost certainly show that you have limited
experience (and infer low pre-selection by other females). When the interaction is
going well just assume that you can kiss her and you should go for it. Just try and
if she refuses, act like nothing happened and continue the conversation as normal.
Obviously never force yourself on her but sometimes you might need to try more
than once to get the kiss. Usually if she is attracted, you should get it. In general
you should always lead, whether it's going for the kiss, changing venue or taking
her home. Just take action and if she refuses just stay cool and calm like it's no big
deal, it shouldn't be.

5 Pickup Question Guide

Do you have rape fantasies? What do you think about death?

Avoid mentioning rape, death, extreme violence, anything creepy or scary in any of
your conversations with women, it's a serious attraction and trust killer.

What is your favourite pet/colour/currency/etc?

These are just boring topics. You are most likely not even interested in knowing
the answer to any of these questions. You might think that you are building
rapport with her but most likely you are just boring her to tears.

If you really don’t know what to say or ask her just look into her eyes and smile,
silence is better than being a motor mouth who asks dull questions. Being
comfortable with some silence demonstrates confidence, and allows her to chip in
and re start the conversation. Introducing some silence in your conversation can
help you to gauge her interest/investment level.

Where do you see yourself in 5 years time?

These cliche job interview questions are bad even during a job interview.

Where did you buy your mascara/dress/handbag/etc?

Are you really interested to know that? These are questions her female friends ask
her. Asking these questions signals to her that you're not a real masculine man or
worse an insecure man trying too hard to make her like you. Leave girly topics for
her girl and gay friends.

Do you like me? Would you like to see me again? Do you think I'm
good looking?

Asking these types of questions shows massive insecurity. Always assume the best,
assume she likes you and wants to see you again.

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Do you have a boyfriend? Do you miss your ex boyfriend? Who is the
lucky guy?

Attractive women will almost always have some sort of boyfriend as well as several
orbiters around. If she is talking to you it probably means that she is ready to
forget about other guys if you are good enough. If she still misses her ex then it’s
time she forget about him.

Which famous person do you think I resemble?

On one hand this question might look like a sign of cockiness but it just shows
insecurity. It telegraphs that you need her to confirm how cool or handsome you
are. Avoid such approval seeking questions.

Are all girls from your country/city so beautiful?

You are putting her on a massive pedestal. She'll probably start viewing you as a
low value man with low standards ready and desperate to go for any pretty girl
from the same region.

Are you religious? Have you heard of Joseph Smyth?

Religious discussions or debates are attraction destroyers, trying to convert

someone is never a good idea. If she asks you about your religious views, tell her
that you don't like to discuss religion. If you prefer to tell her, do so, but don’t get
deep into it. If she is religious show that it’s not a big problem for you and then
move to next topic quickly.

Who are you voting for in the next election? Do you believe in
global warming?

Even if you agree with her political views you are not going to create any
additional attraction, if you disagree with her views it might only lead to a
pointless discussion. Remind yourself of what your goal is; to sleep with her, not to
become her debate buddy.

7 Pickup Question Guide

Pickup Questions
So you've approached the girl that caught your Note: We left some space for you under each
eye, you've spoken with her for a bit but now question to write down your answers. It's
the conversation is beginning to get dry. You can important to be able to reply to each question
revert to one of these questions which should yourself as women may ask for your answer. If
open more interesting conversational threads; she's asking you questions and showing interest
in you, this is usually a good sign that she is
attracted to you. So be prepared!

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What's one of your most expensive purchases?
Tell her what a brainwashed materialistic drone she is, then launch into a diatribe
about the rot in our system (just kidding).

What shop do you never feel guilty spending money in?

Street Pickup.

A work of art that inspires you.

Art Gallery Pickup.

What compliment do you get most often?

How do you usually entertain yourself on a day/night like this?

9 Pickup Question Guide

What fantabulous plans have you got for the rest of the day?

What is your favorite spot around here?

What is the first thing you notice in a man?

Where are you from?... (her answer)

What do you miss most about that place?

What do you do?... (her answer)

What inspires you to do it?

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Where do you live?...What sort of housemate are you?

What 3 things make you stand out from the crowd?

Do you feel desired by men?...What makes you think that?

In what way are you different from each other?

When talking to two girls.

Do you have a nickname? Who uses it? How did you get it?
When you forget her name or when exchanging telephone numbers.

11 Pickup Question Guide

Rapport Building
Generally before you can move into seduction You: "I can imagine just
you need to build some rapport with a girl first. how exciting and thrilling
To create a sense of connection, you want to
actively listen to what she says, reply back with
that would feel! It reminds
a statement or question which will encourage me a lot of….!"
her to expand further on the topic.
If she said something that you agree with, tell
It's best to get her to elaborate on a topic that her why you agree, you create a connection with
she has an emotional attachment to. If she told her by exchanging common experiences and
you that she's an architect, you could point to a ideas.
building and ask what she would change about
its design and why. If you disagree with her, give the reason first and
then say that you disagree, your aim however
If she told you that she’s from Barcelona, a good isn't to start an argument or a long winded
question would be "What's your first memory debate.
of Barcelona?" It would be an error to quickly
move onto the next topic or start listing cities Use her name now and again throughout the
in Spain that you've visited. Don't divulge too conversation. This reinforces her name in your
much about yourself, you want to get her doing mind but also helps to create a bit of extra
more of the talking. rapport.
How much she invests into the conversation is Adopt a non judgemental carefree attitude that
often what differentiates between her staying will encourage her to open up.
and leaving, between you taking her home or
going home alone.You want to show empathy Some questions which could be used to create
and build on her statements, for example; a interesting conversation thread to develop
rapport;
She tells you about her kayaking adventure ..

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What do you usually order to drink at the bar?

When was the first time you got drunk?

What drug would you take if it didn't have any side effects?

What film really frightened you?

What TV show have you never missed an episode of?

13 Pickup Question Guide

What is the most famous person you have ever spoken to?

Do you have any funny habits?

What habits of other people do you find ridiculous or annoying?

What's your most favourite movie from childhood?

What do you normally do when you are pondering a difficult

decision?

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What three words do you overuse?

What was your most impressive sporting achievement?

What would be your ideal job if you never had to worry about
money?

Who was your worst flatmate?

What's something you shouldn't tell people but often do?

15 Pickup Question Guide

Getting More Emotional
You want the girl to open up to you, the more deeper questions. Your questions should have
she unravels the more she'll feel that she likes an emphasis on passions and feelings. Be
and trusts you. She needs to trust you, at least careful not to batter her with one question after
enough, to feel comfortable and willing to go to another, it's too intrusive and she'll begin to feel
an isolated place with you. Remember isolating interrogated and uneasy in your company. Ask
her is necessary if you're to sleep with her. If she her a few good questions and try to get her to
doesn't trust you then she won't have sex with do most of the talking. Make sure to not sound
you, some girl will even tell you that! hesitant, ask each question in a cool confident
tone. Here are some questions that are good for
You want to show her that you 'get her' on a connecting with her more deeply:
deeper level, to do this, you need to ask her

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How do you love to relax?

What is something you lost or thrown away and would love to have
back?

When was the first time you fell in love?

When was the last time you dumped someone?

Tell me something you have owned since you were a child.

17 Pickup Question Guide

Tell me something about yourself that you never told anyone else.

What’s your favorite book from childhood?

What film made you cry?

What movie can you watch again and again?

What music do you love to listen to but don't admit to?

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Do you have any phobias?

What is your favorite place in your flat/house?

What album changed your life?

Would you say that you’re a romantic?

What do you wear when you want to look attractive?

19 Pickup Question Guide

Getting Sexual
Many guys end up walking home alone after a A deep steady voice low in volume can be very
date simply because they've been scared to take seductive to a woman even if the actual words
a risk and escalate sexually. Other guys get too you're saying aren't sexual in nature.
sexual and explicit too quickly and scare off a
girl that they could of otherwise successfully Don't start sexually escalating (physically or
seduced. verbally) if she hasn't given you any indicators
of interest first. Once she's given you IOIs start
The critical thing is balance. Never expect a off slow and light with the sexy questions and
woman to push things forward, it's your job then build it up .
to initiate and to lead. Make sure to escalate
gradually and smoothly as the interaction If you find that she is receptive to your sexual
advances. Just a couple of well delivered questions, you can the escalation to the physical
questions can change the vibe of the and go for the kiss.
conversation and make it more sexual.
Here are some examples of questions you could
When sexualising the conversation make sure use;
to lower your voice both in volume and in tone.

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Are you trying to flirt with me?
Deliver this is a fun playful tone. This question flips the script,
were you're pretending that she is trying to seduce you.

What part of your body are you most proud of?

What kind of music turns you on?

Do you like your hair pulled?

What is the sexiest thing a man has ever told you?

21 Pickup Question Guide

Do you enjoy the feeling of a man’s beard on your skin?

What’s the most romantic place you ever been kissed?

What’s the most adventurous place you’ve had sex?

What part of your body do you most enjoy being kissed?

What part of a man’s body do you find most attractive?

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What are your most feminine qualities?

Which aspect of sex do you think is most underrated?

What’s one of your unfulfilled sexual fantasies?

How do you think it would feel to share a bath filled with fruit jelly?
A strange question taken from the song 'Sensual Woman' by Herbaliser.

That top/dress/shirt that you’re wearing, is it hard to take off?

23 Pickup Question Guide

General Questions
Here is a list of some more questions that you
can may consider asking her;

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Describe your dream flat or house.

What are three of your favorite books.

Have you ever read your partner's diary or emails?

What game have you spent most time playing

What pointless thing do you spend time on but can't give up?

25 Pickup Question Guide

Which skill do you wish you had?

What was the friendliest country that you've been to?

What is the first thing that you do when you get back from holiday?

Who was your favourite teacher? And why?

You remind me of my english teacher...

Who would you choose as your fantasy parents?

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What do you admire most about your parents?

Do you have a favorite sibling?

If you were not related to your siblings would you be friends with
them?

The best concert you've ever been to.

Have you ever walked out on a date?

27 Pickup Question Guide

We hope you’ve learnt a lot, go out and practice, have fun! If you want training to
improve your game whether you are a beginner or already at an advanced level of
game, please visit our website: street-attraction.com or email
eddie@street-attraction.com.

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