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My friend Ryan had spent most of his twenties deeply focused on his career. He was immensely proud of the fact that he could sit alone and work for hours. But in the last few years, he had started feeling an intense sense of isolation that he knew he could no longer distract himself from.

At first, it manifested as a low-level anxiety or a mild sense of restlessness. Later, he felt as though he was stuck in a rut, doing different things but feeling exactly the same flatness — a sense of numbness that persisted.

As an introvert, Ryan had always just told himself he didn't really "need" people. But he finally had to admit the truth to himself - he was lonely.

So, he did what most people do. He packed his social calendar full of events. But when I asked him how that was working out for him, his response surprised me.

“It feels lonelier,” he finally responded.

Like most people, Ryan was confusing the concepts of solitude and loneliness. Solitude is about not having physical companionship while loneliness is about not having emotional connectedness.

For Ryan, his loneliness was actually intensifying during these social events because he was constantly being reminded of the potential for connection but never finding the satisfaction from it. It was like being hungry at a buffet where there was plenty of food, but you were allergic to all of it.

He would attend regular dinner party or games night with people and find himself making the same small talk conversations over and over again. Whenever he caught up with old friends or family, he realized how little he would share about what he was actually feeling. He kept going on dates with high value women where he had great intellectual conversations but would never feel a spark.

He soon realized that he could always think of a dozen people he could call when he wanted to watch a movie, and no one when he was feeling anxious.

He was worried that there was something wrong with him. If he couldn’t find connection with people who were most like him, with people he spent the most time with, or with high quality humans — does this mean he was incapable of ever finding it?

The good news for Ryan (and perhaps for you) is that he didn’t necessarily need to change the people he was interacting with. Just how he was interacting with them.

Emotional Intimacy versus Intellectual Connection

To understand why Ryan was always having great intellectual conversations with people but never feeling emotionally connected, it’s worth knowing that different parts of our brains process thoughts versus feelings.

In the 1960s, neuroscientist Paul D. MacLean proposed that distinct parts of our brain were largely responsible for certain functions — a model he called the “Triune Brain.” Simplistically, the main components of this triune model are the neocortex (thinking), limbic system (feeling), and the brain stem (instinctual/survival).

Ryan, like most people, was only using the “thinking” part of his brain and consequently activating the “thinking” part of the person he was talking to. So, what he needed to do was shift to the “feeling” part of his brain in order to create an emotional connection.

Basically, no amount of using the “thinking” part of your brain will help you connect to the "feeling" part of your brain and theirs.

If you're one of those people that seem to have a lot of great intellectual conversations but struggle to feel a spark or intimacy, I just published an article on how to shift gears to the “emotional” part of your (and their) brains. It's easier than you think, and you can actually start having more emotionally attuned conversations without necessarily being more knowledgeable or having a better vocabulary around feelings. Here's an example of how:

1. Ask “Feeling” versus “Thinking” questions

It’s easy to differentiate between “thinking” and “feeling” questions. Feeling questions tend to contain an emotion in the question or the response as opposed to information.

It’s also easier than you think to flip any “thinking” question to a “feeling” question. Here are some examples of common small talk questions that can be flipped.

Though the difference in the questions is subtle, “feeling” questions tend to open more doors to further conversation than “thinking” questions, especially if you continue to follow the emotion.

If you're interested in reading the rest of the tips, click on the buttons below to read for free.

*Many of my introvert friends that I've shared this article with wanted more step-by-step conversation guidance on how to get to the more emotional space. Since I couldn't fit that into an article, I created Conversation Playbooks which will show you exactly how to go from "Hello" to deeper conversations. This will be a paid, regular newsletter for those who want to go beyond concepts to detailed actions when it comes to connecting better with people.

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