Never Run Out of Things To Say on a Date
Summary
TLDRIn this video, Sterling Cooper, an award-winning adult film star and former high-class male companion, offers advice on keeping conversations flowing during dates. He shares various conversation starters and strategies to reveal a woman's values, dreams, and desires. Cooper emphasizes the importance of making the woman talk more, as it increases her investment in the interaction. He provides questions that lead to effortless conversation, such as asking about high school experiences, travel aspirations, and dating in different cities, all while subtly demonstrating your own attractive qualities.
Takeaways
- 😀 Stay engaged in conversation by asking questions that reveal a person’s values, dreams, and desires.
- 💬 On a first date, aim to get the other person to talk more, which increases their investment in the interaction.
- 🗣️ Ask questions about her past, like 'What were you like in high school?' to learn about her development and personality.
- ⏳ Another revealing question: 'If you could travel back to any point in history, where would you go?' This uncovers interests and knowledge.
- 👀 A fun question to ask: 'What’s it like dating [city] guys?' This sets the stage for playful, relatable conversation.
- 😅 Discuss funny or awkward experiences by asking about 'worst date horror stories,' which also allows you to subtly highlight your high standards.
- 🔮 Ask 'If you could give your 12-year-old self advice, what would it be?' to explore their regrets, vulnerabilities, and goals.
- 🕵️♂️ Play a voyeuristic game, like guessing if other couples around you are having sex or the stage of their relationship, to bond.
- 🌍 Ask about travel dreams with 'If you could go anywhere in the world, where would it be?' to learn about their aspirations and share your experiences.
- 📚 Tailor conversation topics to your own expertise, like asking about books, movies, or other interests, to keep the conversation flowing and demonstrate knowledge.
Q & A
Who is the speaker and what is their background?
-The speaker is Sterling Cooper, an award-winning adult film star and former high-class male companion. He provides advice on improving one's sex life and dating skills.
Why is it important to keep a conversation flowing on a first date?
-Keeping a conversation flowing is crucial for building rapport, revealing values, and creating a comfortable and natural connection. It also helps the person feel invested in the interaction, increasing the likelihood of success in dating.
What are some of the key strategies mentioned to facilitate conversation on a date?
-Key strategies include asking questions that reveal personal values, dreams, and desires. Examples include asking about high school experiences, hypothetical historical periods of interest, or worst date horror stories. These questions keep the conversation engaging and insightful.
How can asking 'What were you like in high school?' help in a conversation?
-This question allows a person to reflect on their past and share how their values and personality developed over time. It gives insight into their background and creates an opportunity for them to elaborate on their personal growth.
What is the purpose of the question, 'If you could travel back to any point in history, where and when would you go?'
-This question helps reveal the person's knowledge and passion for history, as well as their interests and values. It can also lead to deeper discussions about personal desires and aspirations.
How does asking 'What's it like dating [city] guys?' contribute to the conversation?
-This question is designed to elicit a candid response about the local dating scene, leading to a shared understanding or camaraderie. It often opens the door for lighthearted, playful exchanges about dating experiences.
Why is sharing a 'worst date horror story' effective on a date?
-Sharing a worst date story encourages humor and vulnerability while allowing each person to showcase their standards and values. It also creates a light and engaging conversation dynamic.
What does the question 'If you could go back in time and give your 12-year-old self advice, what would it be?' reveal?
-This question uncovers personal regrets, insecurities, and life lessons, providing insight into a person’s vulnerabilities and how they've learned from past experiences.
What is the 'Are they [ __ ]?' game and how does it work in a dating context?
-The 'Are they [ __ ]?' game involves observing other couples in a bar or lounge and guessing their relationship status or dynamic. This playful activity encourages bonding, creates a sense of shared conspiracy, and showcases social awareness and body language interpretation.
How can you tailor travel-related questions to your own interests if you're not well-traveled?
-If you're not well-traveled, you can adjust the question to align with your personal expertise, such as asking about favorite books, movies, or other interests. This allows you to demonstrate your knowledge in your specific area while keeping the conversation engaging.
Outlines
🗣️ How to Avoid Awkward Silences on Dates
Sterling Cooper, an award-winning adult film star and former high-class male companion, shares tips on how to keep a conversation flowing during a first date. He emphasizes the importance of guiding the conversation to learn about the other person’s values, dreams, and desires. Cooper highlights the irony that while men need to carry conversations on a first date, women often talk more when in a relationship. He advises asking questions that allow women to talk about themselves, making the conversation feel natural and effortless.
🎓 First Date Conversation Starters: High School and Values
Cooper shares one of his favorite first-date questions: 'What were you like in high school?' This question encourages the other person to reflect on their past and helps to reveal their values and the path that led them to who they are today. He suggests men should be prepared with their own answers, subtly framing them to highlight their attractive qualities. Another powerful question he suggests is about traveling back in history, which can reveal someone’s interests and knowledge.
🤔 The Ultimate Intimacy-Building Questions
Cooper explains a question he always asks: 'What's it like dating [city] guys?' This question builds intimacy and allows for shared experiences about dating, making the conversation playful and engaging. He follows up with another personal question: 'What’s your worst date horror story?' This question allows both people to exchange funny stories while subtly demonstrating Cooper's high standards in dating.
⏳ Reflecting on Regrets and Life Lessons
One of Cooper's favorite questions is, 'If you could go back in time and give your 12-year-old self advice, what would it be?' This question uncovers insecurities, regrets, and areas where someone feels they could have done better. It helps identify vulnerabilities and potential red flags while also providing insight into the other person’s aspirations and unachieved goals. Cooper suggests this question can also be useful for gauging emotional depth.
👀 The Fun and Revealing ‘Are They [___]?’ Game
Cooper introduces a voyeuristic game called 'Are They [___]?', where a couple observes other couples in a bar or lounge, guessing their relationship dynamics. This game creates a sense of ‘us vs. the world,’ establishing a comfortable, fun atmosphere. It also allows you to showcase knowledge of human interactions and body language, which Cooper considers attractive traits in dating. The game enhances connection and reveals insights into both partners' perceptions.
🌍 Exploring Travel Desires and Expertise
Cooper recommends asking about travel destinations, as it reveals the other person’s dreams and desires. This question also allows him to subtly showcase his extensive travel experience without appearing boastful. He suggests adapting the question based on your expertise, whether it's history, books, or movies, allowing you to guide the conversation into an area where you feel confident and knowledgeable.
💡 Additional Dating Tips and Practical Advice
In the final paragraph, Cooper concludes by promoting additional dating advice through his playlist. He emphasizes that there is much more to learn about dating, hinting at the value of his further content for those interested in mastering first-date conversations and beyond.
Mindmap
Keywords
💡Conversation Flow
💡First Date
💡Values, Dreams, and Desires
💡Open-Ended Questions
💡Self-Disclosure
💡Dating Horror Story
💡Us vs. the World Dynamic
💡Body Language
💡Demonstrating Expertise
💡Storytelling
Highlights
Avoid awkward silences on dates by learning key conversation techniques.
Lead the conversation on a first date, but aim to get her to talk more for deeper engagement.
Women enjoy talking about themselves, so ask questions that allow them to share their values, dreams, and desires.
Prepare answers to potential questions to present yourself in an attractive and confident way.
Ask 'What were you like in high school?' to learn about her background and development.
Use questions that lead to effortless conversation, like 'If you could travel back to any point in history, where would you go?'
Ask 'What’s it like dating [city] guys?' to create a dynamic of familiarity and shared experiences.
Ask 'What’s your worst date horror story?' to prompt lighthearted, playful storytelling.
The 'If you could go back in time and give your 12-year-old self advice, what would it be?' question reveals insecurities and vulnerabilities.
Play the 'Are they [expletive]?' game to analyze couples’ dynamics and body language together in a subtle, playful manner.
Ask 'If you could travel anywhere in the world, where would you go?' to explore her dreams and reveal your own experiences.
Demonstrate your expertise by tailoring questions to your strengths, such as asking about history, books, or movies.
Reframing questions allows you to share personal experiences and stories without seeming boastful.
Asking about travel preferences can create engaging conversations and allow you to demonstrate your knowledge subtly.
Choosing conversation topics based on your expertise lets you showcase your strengths while keeping the conversation flowing.
Transcripts
do you want to avoid those awkward
silences on dates forever well stay
tuned my friend i'm going to give you
some secrets to learning exactly how
[Applause]
my name is sterling cooper i'm an
award-winning adult film star former
high-class male companion and i'm here
to help you improve your sex life
knowing how to keep a conversation
flowing is a crucial skill when it comes
to having success
in your dating life in particular on the
first
date so in this video i'm going to give
you guys some conversation topics that
you can use some questions you can throw
out there that are going to allow for
seamless never ending almost effortless
conversation between you
and a girl the key to this is to find
topics and questions that allow you to
reveal a person's values a person's
dreams a person's desires and what
shaped those values dreams and desires
on the first date you're going to have
to lead a lot of the conversation but
ideally you want her to be talking a lot
because the more she talks the more
invested in the interaction she is and
the more you're gonna find out about her
and the more she's gonna eventually find
out about you and the two of you can get
to know each other as women like to put
it it's the ultimate irony that uh on
the first date or when you're first
interacting with a woman you have to
carry the conversation you have to
actually get
her to talk it takes effort and focus to
actually get her to talk but then once
you're in a relationship with a woman
they don't ever want to shut up they
never want to stop talking and what is
every woman's favorite topic
herself so the key here is also to ask
questions that allow her to talk about
herself in a positive way and allow the
two of you to start flowing back and
forth
in a very natural conversation almost
like you've known each other forever it
doesn't feel
forced in any way it feels
comfortable and very natural now if
you'd like to learn all of my tips and
strategies for succeeding and getting
laid on the first date then i highly
suggest you check out my ebook right
here
so here are some of my favorite
questions to ask on a first date that
lead to practically never-ending
conversation the first one is one of my
favorites and it's
what were you like in high school
you might want to elaborate a bit more
with that question and uh and kind of
lead her a little bit by saying
something like
were you the were you the popular
cheerleader type or were you like the
nerdy
shy
hanging out in the chess club kind of
girl right
most girls you're painting like two sort
of extremes most girls are to try and
say something like oh i was
i was the normal one in the middle
that's what most of them are going to
say but
you allow her to elaborate on the kind
of girl she was and then how she became
who she is today you're probing for
evidence of how she developed her her
values her dreams and her desires today
by finding out okay who was she and
where did she start from and obviously
this can go these questions go back and
forth between the two of you so if you
ask her that question she's going to
want to know your response as well so
with all of these questions by the way
it's actually useful for you to have
an idea of what your answer is going to
be because you're you know what the
question is going to be so your answer
can be a very attractive one right you
can you can frame your answer in a way
in a subtle way that makes you
look very attractive you can
layer in lots of different attractive
traits and qualities in your
storytelling another question i like
which reveals a lot about someone's
values and desires is if you could
travel back
to any point in history
and be an observer and watch
what's going on
where and when would you travel to this
also tells you a lot about someone's
knowledge of history by the way if
someone is a complete nerd on a
particular period of history well bang
you you've just
found out a ton about what they really
enjoy and what they're interested in you
can go down that rabbit hole as far as
you like one question that i without
fail will ask on every single date i go
on and it's a fantastic
question to ask because it allows the
two of you to get really close and it
allows a woman to feel like she's known
you a long time because it's a very
like not so much intimate question but a
very uh revealing question
and it lets you it lets her guard down
quite a lot it makes you seem a lot more
comfortable and relatable and creates
this kind of dynamic of
us versus the world and that question is
well depending upon what city you're in
i will say what's it like dating miami
guys
all right so if you're in chicago what's
it like dating chicago guys if you're in
london what's it like getting london
guys right
and
at least here in miami all the response
is always the same it's like oh it's
terrible
they're all players blah blah blah blah
so
i also like to follow that up with
what's your worst date horror story and
then i follow up with my worst date
horror story which is always a story
about me rejecting a girl for being
i i have it's i'm not going to tell you
the story right now but
it's a it's it's a very
it makes me look like a dude who has
high standards
and enforces those standards right so i
use that as my my horror date story when
she asked me for mine right so we go tit
for tat like this and it's always a
funny playful conversation that comes
out of this question another one i
really really like is and this is
similar to the first question
but it's slightly different in that i
say if you could go back in time and
give your 12 year old self some advice
what would you tell them
because this reveals things about like
her regrets this like her regrets in
life maybe areas where she she's felt
she could have done better uh it's it's
actually reveals a lot of insecurities
and vulnerabilities about a person when
you answer if if someone answers this
question very honestly so
you can maybe uh
maybe you can look out for some red
flags in by asking this question
maybe you can or maybe you can learn
again more about her dreams and desires
and where she wants to go in life but
hasn't necessarily gotten there yet a
really great game that i know a lot of
my friends use as well on dates is the
are they [ __ ] game
so oh it's a very it's like a
voyeuristic
uh people watching kind of game so the
two of you are there and again this it
creates this kind of dynamic of
you and her against the world or like
this sort of secret conspiracy between
two of you it takes you kind of out of
the
where on a date
kind of framework and puts you in more
of a framework of
oh
we're we've known each other forever
we're comfortable with each other this
is
calm relaxed natural following
conversation so that are they [ __ ]
game is really simple if you're in a bar
the two of you all you're sitting down
together
you just play the game and you look
around at everyone else all the other
couples
in the room
and you and you
sit there together and you deduce by
reading their body language
and obviously not being loud and a bit
about this you're being subtle right and
that is part of the fun in the game you
have to be you have to be subtle and
point people out without pointing at
them and stuff
and it allows you to
uh it also allows you to express your
knowledge of social interactions express
your knowledge of body language express
your knowledge of human dynamics these
are all attractive qualities by the way
and so you can look at all the couples
around the room and figure and between
the two of you figure out are they
having sex is this the first date
are they in a relationship have they
known each other for a while are they
are they newly hacked is this like a
honeymoon phase like you can see and
observe all these different couples and
make a judgment on where they're at in
their relationship so that is always a
super super fun game to play especially
if you're if you're in a quiet lounge
bar where there's lots of couples around
it's a fantastic game to play one
question i like to ask that falls into
my particular wheelhouse is if you could
travel anywhere in the world
where would you want to go now
i'm a very very seasoned traveler i know
a lot about a lot of different places
around the world i've been to tons of
cities tons of countries i know a lot
about little bits of little cultures all
over the planet subtleties in different
cultures so
it's actually a way for me to
demonstrate not in a braggy
way in a
subtle humble way but me to demonstrate
that i've traveled quite a bit and i
know a lot about the world but it also
reveals again
where
she wants to go in life what her dreams
and desires are where would she like to
travel to and then i come in and again
i'm not trying to do it in a braggy way
but she'll obviously ask me the question
back and then i can tell well look it's
it's really a toss between
my favorite place in the world like i
like i like seoul i like but i also like
rio de janeiro but i also like this like
uh book arrest and you can in every
place has a different story right so i
can actually continue on and and tell a
whole bunch of stories about my travels
and i can bring up some photos from my
instagram i can show you some some
places i've been to it actually allows
me
to never run out of things to say
by actually asking her that question now
you might not be as well traveled as me
so you can
reframe this question to be
to whatever suits you to whatever your
wheelhouse is so maybe you're
maybe like a history buff or maybe
you're
really well read maybe so your question
might be you know
what what's your favorite book maybe
you're a tv buff maybe you're a movie
buff what's your favorite movie and then
you can go down a rabbit hole of your
area of expertise but you're fr you're
picking a question that is going to
allow you
to elaborate and and
demonstrate
your particular area of expertise and
knowledge now if you'd like to learn
some more practical dating advice for
single guys then i highly recommend you
check out this playlist right here
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