How to Make a Real Connection with Someone: Part 2 – The Magic Word

The “Magic Word” She Really Wants to Hear

How to Make a Real Connection with Someone: Part 2

(Read Part 1 here!)


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?”)

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.

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.

P.S. Curious about some of the science behind why this works? I go into that a little bit in How to Make a Real Connection with Someone Online: Part 1 here.