Chapter 2: How To Ask Someone Out On a Date

Part I: Be Simple and Precise

There was a brief period in my life where my buddy, Prajwal, and I would walk around the
streets of New York trying to meet beautiful women. Our tasks were simple: if you see
someone you are attracted to, walk up to them, introduce yourself, have a conversation and
see if you’d like to go on a date with them. It sounds strange, but the idea behind it was quite
effective. For starters, this was New York. All types of awesome and beautiful people live
here. Second, we were both young, single, and attractive men. Third, we wanted to make
sure we met enough people to learn what we like and dislike. We wanted to experience the
dating life in New York City. But more importantly, we did it because it was exhilarating. The
entire process would take our breath away. The fear of rejection, the fear of being laughed
at, the excitement of discovering someone entirely new and the wild confidence boost you
would get from executing a random, high stakes conversation well- all rolled into one. This
was an adventure sport-level adrenaline chase on the streets of New York.

Besides, New York was kind to us. People did not always appreciate being engaged by
random strangers, no matter how attractive or charming, but the spirit of New York tolerated
us. A lot of other places in the world do not allow for this kind of experimentation, but the
worst New York ever offered us was a ‘no, thank you’ with a forced smile. I don't blame us.
We were, as they say– young, wild, and free. I am even glad we did that. The rejections
hardened us and the attempts that worked gave us a sharp instinct for reading conversations
and interactions. The process of just pushing ourselves to do that created a well of
confidence in us. We came out smarter from our experiments.

My golden takeaway from our phase of experimentation is that communication around dating
worked best when it was kept simple. People spend too much time thinking what to say,
what to text, what to think, what to expect, and they inevitably complicate their situation.
People think there is some kind of a magic formula to dating, something unattainable or
beyond their reach, and thus they make exaggerated attempts at finding a partner. In truth,
dating should be a lot simpler, a lot more natural and a lot more mutual. So, as the first step
of trying to learn how to ask someone out, I must insist that you unlearn all that you have
learnt from culture about dating. No grand gestures, no over-promising, no playing games
and no witty one-liners. The golden words to ask someone out on a date are simple, precise
and honest. Repeat after me these golden words-

“Hey, I think you are very interesting. I'd like to take you out on a date and get to know you
better. Would you like to get <insert beverage, food, activity etc> with me at some point:”

That's it. Then wait for their response.

Part II: Four Possibilities

There are four possible responses. A ‘yes’, which is a green light and you must now proceed
to make concrete plans for sometime fairly soon. A hard ‘no’, which is a red light and you
must politely excuse yourself away from that situation. Clearly you were misreading the
situation, and there is no loss in owning up to it with maturity and poise. However, you will
rarely ever hear a hard ‘no’, especially in in-person instances. People don't say hard ‘no’ in
these circumstances because either they do not wish to invite retaliation from you or they
don't want to hurt your feelings, or both. In these cases, people say a soft ‘no’. A soft no in
itself is a signal of slight discomfort because there is a difference between what is said and
what is felt. You have to be sharp enough to catch them trying to do that and immediately
give the other person space enough to feel comfortable and free with you again. The fourth
type is a hesitance. It is usually communicated in some type of confusion about the prospect
of you dating. It is often a signal that there is a certain obstacle in the prospect that the other
person foresees. If you are met with hesitation, ask them politely ‘What’s gotten you
confused?’. From there, try and see if you can solve that problem. If yes, great. If not, no
problem.

It is of concern to me, and thus I should mention this, that people confuse response type 3
and 4 very often. This confusion is not small and can have bad consequences. Men and
women end up over-committing to a ‘soft no’ by thinking that it is ‘hesitation’ and that there is
some kind of an obstacle they can solve. This leads to a bad outcome, where one person
remains over committed to a fiction in their head and spends massive amounts of emotion
on it, and the other cannot get rid of a person who sees something that they don't. If you
ever find yourself in a situation where you are unsure whether their response to your ask is a
3 or a 4, ask them. ‘Hey, are you just hesitant? Is there something I can do to see if this can
work? Or is this a no?’. You will know exactly what to do from there.

Part III: In truth, there is no symmetry

Men and women make dating choices differently. The instinct and culture around dating was
formed on the backbone of the evolutionary need for sex, and sex is inherently different for
men and women. For men, sex is cheap. They have a near-infinite supply of sperm and no
9-month gestation period of pregnancy to worry about for themselves. For women, sex is
expensive. They have a limited supply of egss and a long pregnancy and post-pregnancy
period to worry about as a consequence of sex. This difference in gametes leads to
difference in how people interact around sex, and thus around dating. Men can be carefree
about sex. There isn't as much to lose and thus the minds of men are programmed to make
choices of attraction quickly. Women have to be more careful about their choices. Their
investment is more and thus they are programmed to make choices of attraction slower.
However, both men and women don't understand this about the other. Both men and women
think the other makes dating choices in the same way as they do. In truth, there is no
symmetry.

Armed with this information, let us try and unpack how to go about asking someone out
successfully. In all fairness, asking someone out is a type of initiative that rests with the man
by default, and thus a lot of the following parts will be framed from the point of view of men.
Women, if you are interested, feel free to peruse.

Part IV: It is All in the Prep

In an ideal scenario, most of your work to ask someone out should be done before you even
ask the question. The seamlessness of asking them out is the best indicator for how well
your interaction has been with them up until now. It should be organic, as if going on a date
is the next logical outcome of this and you both recognise it. That is the magic territory. For
that to happen, you need to remember three basic things- intrigue, intent and comfort.

Part V: Intrigue, Intent and Comfort

If leading up to the ask out, you have managed to establish these three important messages
in your communication, your ‘asking out’ will be smooth. The first is intrigue. Intrigue is not
mystery or suspense, intrigue is interest. The funny part is that our mind closely associates
what we find interesting to be what we find attractive, especially when you are young. If you
give a child a set of ten toys, the child will automatically pick only one. The child’s instinct
guides him or her towards what they find attractive. What do you expect the child to do when
they pick up the toy? Play with it, try to move it around, piece it apart, throw it around.
Basically, explore every possibility with the toy– basically, ask the toy as many questions as
the child can.

We are attracted to what we find interesting, and the formula for building intrigue in a
conversation is very simple- Only say what is required of you, and ask as many questions.
This is the opposite of ‘selling yourself’, which is what men commonly do with displays of
status, wealth and power. This is not to say hide yourself, or the many aspects of you. This is
to only say, let the other person decide what they want to know about you a lot more than
what you want to show them. This is the most organic way of developing intrigue in an
interaction. The more Machiavellian/Robert Greene way of saying this is- Don't say
everything. Leave something unfinished. Leave something to be asked.

If from here, you receive interest from them, in the form of questions, opinions, plans-
conversation in general - you are good to go.

The second thing you have to establish is intent. It should be clear to her that you are
interested in exploring a dating possibility with her before you ask her out. She needs to
have given it some thought. Remember, for her it's almost always a larger investment. You
must communicate your interest in her at least a little bit. Mention to her that you found X
thing she did cute, and that you appreciate Y about her, and try and not always make it
about how they look. This solves the problem on two levels. One, it saves you from the
legendary labyrinth of the friendzone. If she does not want this, you will know beforehand.
Two, it allows her time to think about you in that way.

The final piece in the puzzle is comfort. Comfort is an important consideration, especially in
sexually conservative societies. In societies where people care a lot about who is dating
who, women are the primary victim of gossip and badmouthing. Besides, there is always the
threat of physical danger for a woman when she is in the company of a man, especially if the
man is a stranger. Thus, women often have the need to feel safe before considering dating
possibilities with someone. You will even find, hopefully from experience, that most women
that respond with hesitation to an ask out, often have concerns around comfort more than
intrigue or intent.

So what builds comfort? Comfort is built from sharing. Comfort is built from sharing
information, sharing stories, sharing vulnerabilities, and sharing space. People play when
people share. If one person feels that somehow the other will get more from this interaction
or that they might lose more than they will win, they will not pursue that interaction further.
Very often, men move from a mindset of ‘getting sex or getting love’ and not ‘sharing sex or
sharing love’, and thus appear nervous or untrustworthy in their interactions. If one could
move with the intent of sharing a memorable time with each other, it would automatically
communicate sharing rather than taking or getting. From there, just follow your instinct. Ask
questions about what you're curious about, tell them about yourself where it is useful or it is
asked. Show opinions and passions. Tell them about your past and your future and you will
build immense comfort. Exactly like you do with the rest of the world.

Part V: Executing the Ask-Out

Once you have built intrigue, communicated intent and established comfort, you are ready to
move on to delivering the ‘ask-out’ or the ‘proposal’.

Step 1: Where and How?

Do this in the private company of each other– face to face or over a phone call– the closer
the better. Don't text her a proposal and don't put her on the spot in front of her friends.
Ranbir Kapoor attempted an ask-out in front of Nargis’ friends in Rockstar and Nargis
rejected him harshly. No one likes to be put on the spot.

Step 2: Do not be over convinced of your proposal

Men in India and around often think of asking-out as a proposal that magically transforms
you into boyfriend-girlfriend. Maybe that is the case for your social environment too. Maybe
people around you desire commitment faster. However, you ask-out should not communicate
rabid desperation to commit and own the other person. This is the Bollywood rub-off on all of
us, where either romance is intense or it doesn't exist. Healthy romance exists in the
performance of a relationship, not in the chase of it. Don't over commit in your ask-out. Truth
is even you don't know if you'll truly like the other person or get along and they may not know
that about you either. Frame the ask-out as an opportunity to get to know each other better
so you can then decide if you want to be together at a later, more mature stage of your
relationship.

The converse of this is that you should be asking out potential partners sooner than most of
you actually do. Don't ‘fall in love’ in secret. Fall in love in the company of each other. Enjoy
the process of seeing each other and slowly descending into love.
Step 3: Actually say it

Look at them, pause for a second, smile earnestly and then say it. This is going to be the
most difficult step for a lot of you, especially the younger ones. It was very difficult for me to
learn. You have years of conditioning behind you. The world has taught you that talking to
the opposite sex and considering anything sexual is forbidden. It has also taught you that
romance is pure and ultimate. Neither is true. However, your body might respond with
nervousness and fear. Face your fear. Think- If you can't own up to your own fears, how will
you take care of someone else? Face your fear and say it.

Say - ‘Hey, I think you are very interesting. I'd like to take you out on a date and get to know
you better. Would you like to get <insert beverage, food, activity etc> with me at some
point?’

Or some variation of this. Tailor it to your context. It helps to start with ‘This may sound a little
out of the blue..’ or ‘Forgive me for being totally upfront..’. This pre-framing helps you ease
them into the proposal.

Step 4: Making Plans

Assuming they accept, formulate the set up for the date in proportion to the warmth of their
acceptance. If they are very excited, you can make plans right there and then. In that case,
you can be concrete about time and plans. If it's a softer, somewhat unsure yes, tell them
you'll plan with them over the phone or tomorrow. The point is to give them breathing room if
they feel overwhelmed. Let them make sense of this prospect alone for a little bit. Don't push
too hard.

Part V: How to Deal with Rejection

Rejection is tough and frequent. Believe it or not, everyone gets rejected. I've gotten
rejected, my friends have gotten rejected, the most attractive men and women I know have
gotten rejected. Rejection, if not looked at properly, inspires fear. People think that a
rejection to their ask-out is a rejection of them. It is a very selfish way of looking at the world,
as if the only thing that matters is how ‘good’ you are. People make their choices for 1000
reasons, and we will never figure out what those are. Separate yourself from the rejection.

Secondly, rejections are good because you are filtering out the people it would not work with.
Think about it. So many people are convinced that X is the one and even if X rejects them.
X says they are not interested in them, but those people go on living like X is the one. What
is the evidence? Some strong, yet vague, feeling you have? How do you know you cannot
have that feeling for someone else? True love is found in mutuality and in sharing. True love
is a two-way street. Romance can be a one-way street, and sometimes a very toxic one-way
street. What is the difference? That is an issue for another book. What is important to know
is that rejection is a filtering process. It is the strongest indicator of the fact that maybe this
person isn't the one. You just have to get past your ‘dreams’ of them and see them for the
‘reality’ they are.
Maybe, if you can manage to truly see rejections in a non-personal way, you can be excited
about rejections. However, it is difficult. Usually rejections are deeply tied to self worth, and a
rejection means a deep scepticism about one’s self worth. I have found the most real
alternative to handling rejections is building a strong emotional base in the things you do
everyday. You should do things you respect. You should be proud of your day, your week,
your month and your year. You should work in a way that you respect and love, and your self
worth will not get tossed into a salad every time someone rejects you.

Beyond all this, rejection can be a portal to learn, to be strong– as the many cliches go.
However, you need to get the precursors right to arrive at this indifference. Be excited about
discovering it. However, for the sake of clarity and in the interest of repetition, let me state
the larger point more clearly. Do not pine upon them after the rejection. Let rejection be a
natural signal to move upward. Do not waste time trying to win them, trying to impress them,
or worse trying to intimidate them. Don't waste time fantasising about them and don't waste
time thinking about what it could have been. Take your story forward without them. This is a
test of courage and grace, and this is where self worth is built. Don't be the weakest version
of you when you need yourself the most. Who knows what fantastic person awaits you after
this rejection?