How to Talk to Your Date versus Your Customer



When I was younger, I thought dating was primarily about “impressing” someone enough that they would somehow find you attractive. After discussing this with my therapist, I now understand that my lack of self-confidence led me to feel like I had to “deceive” others to be liked because I didn’t like myself. Thus, inauthenticity.

That line of thinking and mindset led me to be single for a long time, and since then I’ve always paid attention to how I communicate and how I might communicate better. Coming from a nerdy, introverted, engineering background, it has taken me some time to reach my somewhat adequate level of socialization, but I’m enthusiastic to inform the reader that a psychologist friend recently dubbed me “almost certainly not autistic” 😎👍

One of my learnings is that not all communications come equal, which may seem trivial, but between my recent dates and customer interviews I found an interesting set of similarities and differences.


We have three principle responsibilities in a conversation: Listening, Thinking, and Speaking.


I have heard that the best conversationalists spend as much of their time listening as possible, and in my experience that remains true with both your date and your customer.

BUT… What am I paying attention to?

One memorable mistake from my youth was asking for advice in the form of “Do girls like… ?” as though every girl would have the same opinions. The truth is that every date is unique with its own context, and every person with their own expectations. The personal nature of a date means that we learn about our partner not in broad strokes and generalizations but with the individual stories where the details matter most, down to the three sisters she has or the name of her cat.

I still remember vividly the interests of a girl I met in Spain, who was into fantasy novels, BookTok, and had a small tattoo of a dagger. At one point I found these small dagger earrings in a store and I got them for her, and I don’t think I’ve ever made anyone happier than in that moment.

Contrast this with my consulting work, where I’m still listening to the experiences of my clients and customers, but I’m searching for patterns they share with others, such as spending too much time replying to emails, and the individual details often are less important compared to the broader market trends.

When I was working a small video call tool, I talked to a lot of students using the platform for hours on end. We’d zone in on specific details, such as family situation, extracurriculars, and even social relationships, in order to find lookalike audiences to grow our niche. Yet, often the small niches didn’t stick and we ultimately failed. Even though I still think it’s a good strategy to narrow down the audience, we just ignored the greater point, which was that it was COVID times and these kids all just wanted to hang out, even if it was virtually, and our efforts were just significantly less important than the need for socialization.

For me, conversations happen exceedingly quickly, and so keeping in mind the contexts where I need to pay the most attention and what I’m listening for enables me to learn more effectively.


Once I learn something about my conversation partner, I need to put that information to use, relating and transforming it with respect to some thought or opinion of my own.

BUT… What is the end result I want to achieve?

This question guides the direction of my thinking.

I remember a date where I tried to offer solutions to every problem she shared, such as not making enough money (“Well maybe you could do… ?”), or her parents being upset at her (“Have you tried saying… ?”), when the whole time she was seeking empathy, not answers.

To be honest, I still make this mistake often, not just in the dating context but with many friendships, and I have heard it can be a common problem for men, especially engineers. The best response to a friend coming to you with a sad story is often “I’m sorry, that sucks” and not “Have you considered… ?”

This is the opposite with professional conversations. Although clients still appreciate when I understood and relate to their issues, often what puts a smile on their face is hearing the insights and solutions I can provide to those problems, once I’ve understood them.

It’s important to be aware of what role you have in the conversation and how you intend to play that part. I like to be aligned as much as possible with my conversation partner, because I think of good conversations as a team effort.


In all scenarios, we’d like to have our thoughts understood directly by the other party.

BUT… How do I actually present myself and express those ideas?

We are limited to speaking in order to transmit our ideas, and the manner in which we communicate affects how the information will be received. This is an unfortunate weakness of not being robots.

In personal relationships, authenticity is key. When I was younger and didn’t know better, I’d say these Hollywood-inspired cute cringe phrases like “You are perfect,” and people would look at me disgusted because the reality is people can tell when you are being authentic, and those words meant nothing to even myself.

In time, I learned to own the way I feel and who I am, with all my quirks and genuine reactions. I find now that even the smallest compliments can develop stronger connections as long as they they represent you and how you really feel.

In professional settings, while authenticity still matters, I’ve found that there are scripts to follow; Speaking in platitudes and and the expected boilerplate language enables both parties to feel more comfortable and actually builds trust by way of professionalism.


Communication is probably the most important skill we develop in life, so be sure to develop it.

When I was in a big office at Facebook, I found myself primarily learning a lot of technical concepts. They remain useful if I’m sitting down to be an IC engineer in the same company for a long time, but I seek more out of life than that. In the last two years I’ve traveled to 18 countries, making friends in every place and learning so many soft skills that I feel like I am twice the man I was. For example, learning how to communicate better in every nuanced situation, and feeling confident about myself and my lifestyle to present my ideas prominently.

I think the rewards for learning soft skills, especially for someone like me coming from an introverted, engineering background, far outweigh the benefits of learning technical skills. For example, I recently listened to problems of a friend working at Google and helped him navigate his situation to better assert his work/life boundaries to his manager and teammates.

For the reader, if a 2 year odyssey is not available, just keep in mind that the core skills of communication – listening, responding, and understanding – remain constant, but their application differs vastly in different contexts.

It’s all about recognizing what dance you’re dancing and choosing the right steps.

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