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How to Make a Real Connection with Someone

A couple making a real connection

If you’ve read any of my articles or eBooks, you’ll know by now there are 2 things I recommend doing above anything else in online dating:

  1. Asking questions about who someone is and why
  2. Sharing specific detail about who you are and why

Do this in first messages, do this as you continue to message or text, do this on your profile, and do this on a first date.

For a long time, I thought this obsession with asking/being asked questions was unique to me – that this was the only way I felt comfortable getting to know someone, or having them know me.

It’s incredibly important to me that my partner – friend, date, long-term significant other – ask me questions, be genuinely interested in my answers, and have a willingness to share openly in return.  Curiosity and self-disclosure are the foundation (or at least the key building blocks) of my closest relationships.

This has also been the biggest running theme for why I’ve ended relationships.

When someone is not curious about me, or doesn’t seem to know how to be curious, and share who they are in return, I don’t feel we can grow our relationship together.

This really hit me over the head recently, prompting me to examine this universal need for creating connections with others.

I was in bed with a new “man-friend.”  

We’d met on Bumble and for the past several weeks, we’d been sparking with chemistry.  Our rapid-fire banter made both of us feel like hilarious geniuses, we shared an electric need to touch each other, and had that insatiable need to stare at each other's faces in delight/fascination/lust.

But I knew I had to end it. 


After all that banter, he did not seem to give a fuck about my thoughts and opinions about things that matter to me most:

Why I chose to start my own business, what I thought of my parents’ ongoing divorce, how I feel about guns and politics and religion, what I want out of the next five years of my life, or why I experience intermittent insomnia.

How did I know he didn’t care?  Technically, I didn’t.  But what I did know for sure was that he didn’t ask me about any of those things despite me mentioning each one specifically.

In his defense, I didn’t volunteer my own feelings or thoughts, either.  This is a little test I run (for better or worse) to see how much someone really wants to know who I really am inside my head (the stuff that remains after you’re old and ugly) by mentioning something important and seeing if they ask about it.

I was also open to the fact that his strategy for getting to know someone was just different from mine.  Maybe he is observing my actions and then he’ll confirm his impressions of me with me later, I thought.

So, that last morning in bed, I asked him, “How do you like to get to know a person?”

He paused for a long time. (Uncharacteristically long; he’d always been quick with a quip.)

“I don’t know,” he said.

“Well, for example,” I led, “I like to ask someone questions to learn more about their thoughts, opinions, and feelings.”

He was quiet again.  “I’ve never thought about it.”

New course

That’s when I knew it was over.

Several years ago, I might have spent more time leading by example, trying to show him how we could ask deeper questions, have more engaging conversation, and share who we really are with one another.

But recently, I’ve decided to focus on building strong foundations with those who already value this practice from the start of our relationship.  I now need at least some of this as raw material to start with.

Learning that he’d never thought about how he likes to – or tries to – get close to someone was a deal-breaker for me. 

To me, real connection – an honest, vulnerable, curious, non-judgmental desire to understand why and how someone else is in the world – that connection we make with others is what makes life worth living.

When we seek to understand someone else’s perspective, feelings, ideas, motivations, fears, opinions, and thoughts, we can really love them for who they are.

When they try to do the same for us, they can love us – and we can make great partners in all walks of life: friendship, romance, business, the community.

This is the goal, right?  We all want to be seen, heard, and loved.

While this has been a theme in why I’ve ended relationships, it’s also been the predominant quality of my strongest, most lasting, most joyful relationships.

I’ve been doing a lot of research around this, and I now know it’s not just me.

Our need for social connection is hard-wired as a species.

Our brains, specifically the neocortex, are bigger than other species' because of our need and ability to socialize.

Our bodies were built to help us connect with others – to vocalize, touch, and chemically bond with each other.

Two people learning how to make a connection

The big question: How do we make connections with others

How do we learn to connect better given our circumstances – in our world of apps, Snaps, texting – that have arguably dulled our ability to be casually open and naturally vulnerable with each other?

More specifically in dating / online dating:

What do you say on Tinder or Bumble to make a girl more likely to want to talk to you – share who she is, and learn more about you, specifically?

What do you do on a first date to demonstrate you’re genuinely interested in learning who she is on a deeper level?

What is too much, too little, and just right to ask, and to share about ourselves, when we want to have a real chance at real love – and not be back home and swiping again by 10pm?

These are some of the questions I’m going to start answering on MenAskEm.  As always, I’ll try to share the research, and tactical and actionable next steps with you.  But I hope you’ll enjoy the philosophical aspects of this new conversation too.

Thanks, as always, for being one of the good guys who get why this is so important to do, despite it being weird and difficult at times.  (Because if that isn’t love in a nutshell, what is?)

The magic word she really wants to hear...  It’s not please, or beautiful, or even love.  It’s definitely not “heyyyyy…”

It’s why.

Why, you ask?

That’s exactly why!  (Don’t worry, this isn’t about to become “who’s on first?”)

H apps promo

The act of asking someone why? conveys your interest in learning more about them. 

By asking this simple question, you are expressing your curiosity, your desire to understand someone or something better – whether it’s a concept, their opinions and beliefs, their thoughts and feelings, or the reasoning behind their behavior and actions.

When you begin to know why, you begin to know who someone is.

Asking a girl questions to get to know her may seem like common sense, but it can be easier said than done.

Think about the following statements.  Pretend someone said these to you – a friend, a girl you are talking to on an online dating site or app, or even a coworker.  How would you typically respond, either in-person or over text?

“I had a shitty day.”  

“Aw, that sucks!”


“Why, what happened?”

“I really liked that movie.” 

“Yeah, me, too!”


“Me, too! Why did you?”

“I am feeling really down out lately.” 

“Ugh, I’ve been there. You’ll pull out of it.”


“I’m sorry to hear that!  Why, what’s going on?”

“What you said really hurt my feelings.”

“I’m sorry! I didn’t mean to.”


“I didn’t mean to.  Can you tell me why so I can understand how that happened?”

“Wow, I just feel so amazing after yoga.” 

“Aw, that's awesome!”


“Why do you think that is?”

“I disagree.” 

“Well, you’re entitled to your own opinion haha”


“Oh, really? Why?”

“I’m really frustrated right now.”

“Yeah, I can tell.”


“OK, why?  Let’s talk about it.”

If you realized that you frequently respond the first way, you’re not alone. 

Even though we like to think of ourselves as caring, compassionate, and curious friends and partners, the truth is that we don’t always put our money where our mouths are by asking why (or similar questions) to get to know someone, to dig deeper, or to be there for someone.

There are lots of reasons why we don't always ask why.

Which of these feel familiar to you, when you really think about it?

  • We are worried about seeming “stupid.” Asking why? feels like we are admitting that we don’t know something we “should.”
  • We are afraid of getting an answer we don’t want to hear.
  • We may be concerned we’ll look nosy or rude.
  • We want to play it cool and don’t want to look over-eager.
  • We are afraid asking why? sounds too challenging or direct.
  • We think we already know the answer.
  • We’d rather keep things easy and low-key – and asking deep questions makes the conversation get heavy or depressing.
  • We might be freaked out about digging deeper into a topic that feels like we’re on uncertain ground – or that opens into a conversation that requires us to be honest about something difficult, vulnerable, or otherwise uncomfortable.

By not asking why, we are missing two huge opportunities for connection.

First, we give up the chance to receive new information to get to know someone better and therefore to connect with them on a deeper level.  Second, we are losing the opportunity to show someone that we care about them.  The latter is critically important in building a relationship, whether it starts via online dating or offline.

Conveying that we care enough to be curious about someone’s thoughts and feelings is possibly more important than actually understanding their point of view.

In fact, we may not always agree with them, or like what they have to say.  But when we express to someone that they are important enough to us that we care about understanding their thoughts and opinions – and try to receive that information without judgment – we are building trust and setting a precedent for honesty, security, and open communication in the relationship. That's the foundation of a strong and lasting connection.

H apps promo

If why? is a not question you normally ask, here’s how you start.

Ask it!  Seriously.  Just start practicing.  You don’t have to wait for a first date – although asking why? should definitely be on your list of what to talk about – or wait until you’re in a relationship.  The relative anonymity of online dating messages and texting on apps also make those platforms great places to practice!  Put this on your list of what to say in first messages or good questions to ask when texting with a girl.

Or, if you want to try it out on someone you’re already comfortable with before you start practicing on prospective dates – consider someone like your mom, a sibling, or a friend who is already fairly open with his or her thoughts or feelings.

You might also tell someone close to you that you’re working on this so that you can openly “practice on them.”  Explain honestly why this is a skill you’re looking to build, or just mention it casually, like, “I’m trying to ask people more questions instead of just keeping things at the surface level all the time.”

Don’t worry about getting “too heavy.”

If you’re on a second date with a girl you met on Bumble and she tells you she had a bad day or a sad experience, your instinct might be to cheer her up or distract her – instead of going deeper into the subject.  Instead you could say, “I’m sorry to hear that!  Why?  We don’t have to dwell on it, but we can talk about it if you want to!”

Some people are afraid of things getting “too serious” or “too depressing” on a date – or even in normal life when hanging with a friend or partner.  But asking about something “heavy” does not mean you have to dwell on it.  In fact, by asking about it, and letting the person talk through it with you, you may be lightening their mental and emotional load!  The conversation or their attitude may be significantly more positive following the time you spent processing through the “negative” topic together.

Many people (like me!) are verbal processors and we need to talk out our thoughts and feelings to gain clarity, find solutions, and positive resolution.  However, I don’t often share my feelings outright unless I sense someone is interested in going there with me.  If you sense someone might need permission to open up to you, simply let them know it’s okay – and asking why? is a really easy way to show this.

If the specific wording of “Why?” doesn’t feel natural to you, ask in other ways: 

  • What makes you say that? 
  • How so? 
  • I’m not sure I know what you mean; can you talk more about that? 
  • Why do you think that is? 
  • How come? 
  • What happened? 
  • What is your thinking behind that?

The point is not the specific language of the question but the intention behind it.

What if it’s not you, it’s her?

Maybe you’re great at asking why, but the girl you’re messaging with on OkCupid – or having a third date with! – could use some help expressing interest in your thoughts and feelings.

If you get the sense the person you’re talking to is interested in you, cares about you, and would like to know more about you – but needs help deepening your connection – you can model how to ask why? for her!

Here are some ways to show that why? is a question you want to be asked and are comfortable answering:

  • Share a thought or opinion, and then follow it with, “And here’s why I believe that…”  
  • Check in to see if she wants to know more, by saying, “If you’re curious about why I feel that way, we can talk more about it…?”
  • Make it a joke by sharing a thought or feeling and then saying, “Why, you ask?!” before sharing your reasoning.
  • Simply say outright, “If you want to know more about that, or anything else, you can always ask me.  I’m always comfortable talking about why I think or feel a certain way.”

In past relationships, I’ve also raised this issue directly with partners a few times, by saying something like:

“I love asking why you feel or think a certain way because it helps me understand you better!  But I’ve noticed that when I share a thought or opinion, you don’t tend to ask more about it.  If you asked more about why I feel or think a certain way, I’d feel more comfortable sharing that information.  Otherwise, I feel like you’re just not that interested!” 

Depending on the person – and the manner and moment in which I say this (ahem, which I will admit is not always “perfect”) – this feedback has been very well received and led to more successful communication in my relationships.  It has also ultimately helped both of us realize that we are looking for a partner who is a better match for each of us in terms of what we are looking for in our communication styles, emotional intimacy, or simply what we enjoy talking about!

Either way, asking for my needs to be met in this way been successful because, for me, it’s critical to be with someone who cares about me and wants to understand me through verbal communication.

The easiest way for why? to become part of your relationship’s vocabulary is simply to ask it, often.

Your date or partner will see that it’s a natural – and a safe and encouraged – question to ask when you care about the person you’re with and want to know more about them.  The more you ask why? the more she will, too.  Whether it’s on a first date or in your fifth year together, you get to create the foundation on which you’ll continue to grow and connect together.


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