My ESFJ boyfriend thinks relationships are easy. I do not. We have been dating for over two years, which is a new form of miracle for me and really no big deal for him. While it’s been easier than my previous attempts, it’s been far from simple. Because inside my mind I have many, many illogical questions about how relationships work and no logical framework to answer them with. Without these things, I am a ship beneath a starless night sailing in circles until I can bear the siren’s call no longer and crash upon the rocks.

To say it’s all very dramatic would be an understatement.

Impact of Under-developed Feeling

A little information can be a dangerous thing to an ENTP. With our under-developed Feeling function, we believe our understanding of social dynamics extends to understanding relationships and intimacy. It doesn’t.

We do have a gift for understanding how people respond to environmental triggers in specific situations. As we learn through experimentation, we like to mess with the social dynamics to better understand what’s happening. However that gift does not require intimacy, it requires objectivity. Let me give you an example.

In my 20’s I loved having gregarious conversations, from the guy in the lift with the cool tie to my favorite barista. These small, light but ultimately superficial interactions energized me because I was experimenting. What would happen if I….?

During after work drinks, I got bored attempting to hold interesting conversations and instead amused myself with mental games about the best time to approach a stranger. While I thought I was looking for a relationship, what I was really trying to understand was the bar’s underlying social dynamics. And that doesn't require intimacy, it requires objectivity. No wonder I spent so many years being confused as a serial dater!

So, here is the rub for an ENTP. We want deeper relationships with people but fail to realize we have a gap in our intimacy-building skills. It’s a natural consequence of having developed our objectivity. So how do we develop intimacy without sacrificing our talents?

Fear of Routine, Boredom and Constraints

Another blindspot comes from our desire for novelty, new ideas and having space to follow our curiosity. Let’s call this our desire for freedom.

ENTPs have an innate drive for freedom and quickly reject anything that starts to look repetitive or constraining. We learn about the world by making connections between novel information, and we secretly are terrified of the boredom we might endure if the new information stops flowing. Hence we’ll prioritize new experiences over old ones, even with people.

I clearly remember the moment I prioritized my to-do list and my then boyfriend wasn’t on it. It was a week before the film shoot for my latest obsession, a four-part soap opera set on campus. I was overwhelmed juggling my studies with the film project and realized the only thing I was willing to give up was my relationship. A few days later, I let him know and made a bit more space on my plate. It never occurred to me to ask whether he wanted to be involved in the project.

Now, a desperate quest for constant freedom doesn’t lead to actual freedom. The key is finding a balance between the freedom we want and the stability to have it everyday.

The Short Version

For the ENTPs in a rush to get to the highlights, here it is:

  • ENTP love freedom and reject anything that ties them down

  • Complete freedom is a myth and leaves an ENTP without the freedom that matters

  • ENTP excel at superficial human interactions as it helps them understand the wider social dynamic

  • Which can result in an intimacy-building skill gap.

Mental Probing

To settle into a stable, long term relationship requires understanding your own mind and what matters to you—in essence, delving into the TP parts of your personality. Without that, finding freedom within a committed relationship will continue to be a struggle.

Here are a series of questions to help you objectively question the assumptions that create your behaviors. Let the mental probing begin!

1. What do I believe about relationships?

As children, we look to our parents as our relationship role models; later, we may look to our extended family and to our friends. If you lacked a relationship role model like I did, it will be difficult to know what real intimacy looks like. Which means, you may be carrying a number of beliefs that undermine your relationship-building efforts.

Based on these beliefs, we all follow an interaction pattern, a story we act out, but are rarely conscious of. If you want a different outcome, it’s time to bring your subconscious patterning to the surface.

  • What do you believe about relationships?

  • What do you believe is the role and responsibility of each person in the relationship?

  • What you believe about the nature of relationships themselves?

  • What relationship patterns have you observed in your behaviors?

  • What do you expect from a relationship?

  • For all of the above, how could you be wrong?

2. What kind of freedom do you crave?

Until you know the specific kind of freedom you want, you will hate having to let go of any possibility. There are many types of freedom available to you and different identities you could adopt: the wanderer, the inventor, the trickster, the critic. It is only through a process of experimentation that you will become clear on which is you.

Ultimately, you are searching for a reliable way to be consistently creative, in whatever way matters to you. Then you won’t need or want unfettered freedom, you’ll only want the ones that matter.

  • Make a list of all the different types of freedoms you can imagine. Rank them.

  • Which routines or constraints have you adamantly rejected over the past 5-10 years?

  • What sort of stability do you need in your life to make your form of creative expression possible?

  • What freedoms may you need to give up to be in a long term relationship? How does that feel?

3. Who do I want to be next?

One of the hardest things about being an ENTP is the constant search for a clear-and-fixed identity. We desperately want to know who we are, yet there are so many possibilities it seems as if we’ll never find it. As overwhelming as it is, we still are more likely to explore for our work or career than in our relationships.

For many years, I labored under the false belief that I had only a limited role to play in a relationship, to show up, and the other person had to do the rest. It took me a long time to realize that while I had invested countless hours into finding an authentic career, I had devoted next-to-no time to exploring my identity in a relationship.

  • What are the possible selves you could be in your current or next relationship?

  • What could you learn from yourself and your past relationships?

  • What nurturing does your current (or future) relationship require?

  • Are you willing to make that effort?

Relationship Hacking

So, how to build intimacy when we are so good at objectivity? Mental hacking. Take your assumptions about what a relationship should be and flip them on their head. Here are a few ideas.

1. Find a framework

Humans are weird and wonderful creatures prone to irrational behavior, especially in relationships. It can help to find a framework to explain people’s drives, needs and behaviors in these situations. Personally, I gravitated towards attachment theory and love languages.

Tip: Find a framework that explains human behavior in relationships, and play with it in the real world.

2. Change the criteria

The moment we meet someone, we are evaluating then against a range of criteria. This can feel like a gymnastics team gone wild inside your mind—especially if the criteria you are using weren’t created by you but are based on what your parents or peers think are important. This will get you nowhere but in knots.

Ignore them and make your own simple, one word criteria. Yes, one word. What is the one thing you would like more of in your life this year? Fun? Playfulness? Adventure? Pick your word and every time you hang out with your person, ask yourself “Am I having….?” Give yourself permission to follow your instincts.

For me, it was around having fun. It made the whole, do I/ don’t I conundrum much simpler.

Tip: What do you want more of in your life this year? What is your one word? Does this person help you create that? Trust your instincts.  

3. Make it a project, give it a purpose

I do so love a new project—full of energy, time, devotion, a desire to make something better than it was before. The problems come when your projects are more exciting than your relationship. So, think of your relationship like a project. It may seem inappropriate, but try it anyway.

Tip: If your relationship was an exciting project, what would it need?

4. Go adventuring together

NPs learn through feedback from experiments, in this case, social experiments. Quick and responsive feedback really energizes us and helps us understand something, which in turn helps us feel more connected to it (or them).

Without feedback, we struggle to create the connection that helps us to build intimacy. Which means, any kind of physical or emotional distance is going to make it even harder to build a sustainable connection. You need someone who will be quite responsive to your requests for interaction.

Even better, is if they say “yes” to as many of your random adventures as possible. It’s easier to connect with a person in relation to something that is already familiar to you. If you can understand them in a variety of contexts, the deeper the connection will be.

Tip: Assess the level of responsiveness and distance in your relationship. Go on as many adventures together as possible.

When to commit and when to leave

ENTP’s find it a bit too easy to skip out on a relationship. It takes something special for us to commit. Here are some things to watch out for when you are having this debate with yourself.

1. Are you dating the person they are now or the person you imagine they could be?

ENTPs are great at seeing the potential that lives inside people, and our frustration will soon rise if we don’t see the person becoming all they could be. You need to find the person they are now just as interesting as the person they could become.

2. Are you on this adventure together?

While an ENTP wants her version of freedom, she also wants someone who is excited to be a part of her life’s adventure. When you step back and look at the bigger picture of your relationship, are your lives coming together or remaining compartmentalized?

3. How well are you really communicating?

While you value honesty, until you have developed skills in intimacy, you will struggle to find the balance between telling the truth and preserving the relationship. Too much of either is unsustainable. Check in with yourself. What haven’t you been saying enough of? What have you been unnecessarily honest about?

Final thoughts

Intimacy can be a blind spot for ENTPs, and the key to a lasting relationship comes from better understanding our own mental wiring. That means developing an understanding of our personal relationship framework, and what we need to give and receive from a relationship.

Then, my friends, it's about developing a practice of intimacy. Hopefully you have a partner as patient as mine because you’ll screw it up a few times before you figure it out.  

Samantha Mackay

Samantha Mackay is a certified Enneagram and leadership development coach who believes work should be energizing, not draining. She combines the Enneagram with her experience of recovering from burnout twice to help leaders and teams thrive during stressful times. Connect with Samantha at