The Pros and Cons of Having a Rebel Boyfriend: Based on The Four Tendencies by Gretchen Rubin

I love personality quizzes. I think the more awareness and knowledge we have about ourselves, the more capable we are of knowing how to approach others and life with our best foot forward.

As an Airy Leo, ENFJ, Manifestor, Questioner, I love being around people and exploring the meaning of life. Having learned that relationships are one of the biggest indicators of overall happiness, I am constantly trying to understand the people closest to me.

Recently, I was introduced to The Four Tendencies by Gretchen Rubin. In her book and free online quiz to learn your tendency type, she explains how there are four main tendencies that everyone more or less falls into, which determines their ability to meet (or not meet) expectations.

Like I stated above, I am a Questioner. I am constantly asking questions and diving into research in order to understand the world around me as well as what choices to make in regards to consumerism and beliefs. This can be extremely fatiguing and lead me to wanting to pull my hair out with what Rubin calls, “analysis-paralysis.”

Having the never-ending compulsion to seek answers and understanding, I often end up with more questions and a disdain for life. I just want clarity and solidified fact. When it comes to big questions, such as “Why are we human?” and “What is the purpose of life?” I struggle to find conclusive answers, and often find myself in an existential crisis.

Being alone with my ever-growing thirst for knowledge is exhausting. However, I have found myself in a relationship with a Rebel, and that is even more exhausting.

Read on to learn more about the Rebel Tendency and how I’m learning to deal with my relationship.

The Cons of Being in Relationship With a Rebel Tendency 

Rubin describes the Rebel as someone who doesn’t meet outer or inner expectations. Basically, they do what they want, when they want. It sounds immature, right? Well, I can attest from being in a romantic relationship with a Rebel that I constantly feel like he is immature, and this is something my mother has said about my father.

Probably unsurprisingly, my father is a Rebel, which works decently well with my mother, an Obliger (meets outer expectations but fails to meet inner). Rubin states that the Obliger is usually the best match for a Rebel since they can help an Obliger find freedom from too much external pressure.

After observing my parents’ marriage my whole life—they’ve been married for over 40 years now—I would see the things I didn’t like and swore never to allow in my relationships. Even though they are the most compatible types, for the majority of my life, they lacked the constant personal and relationship development that is needed to maintain a healthy relationship. 

I saw the resentment build up over decades between the two of them and vowed to create a relationship devoid of that. I wanted a partner who was more willing to do what was asked without having a temper, and do thoughtful, unexpected things to make me feel special. 

With Rebels, they don’t like to be told what to do or be expected to do anything unless they want to. This characteristic has caused my boyfriend to fail to meet date plans or pretty much any plan. He will put the responsibility on me and lacks any accountability, causing me to feel taken for granted. 

Everyone wants to feel special, and when your partner seems not to care about promises he makes the day before, it’s easy to feel unappreciated and not valued. Unfortunately for the Rebel, they also struggle to meet their own expectations, even if they want to. It’s like there’s a petulant child inside their brain that causes them to do the opposite of what people ask or what they ask of themselves.

In my relationship it often feels like I can’t rely on my partner or trust him. It’s lonely feeling like the person you’re supposed to be able to depend on above all others, is undependable.

While they are the smallest percentage of the population and oftentimes seen as the most troublesome, Rebels have a carefree attitude that can be one of their strengths. Rubin points out every tendency’s strength can also become a weakness, unless kept in check. 

My Questioner strength of finding efficiency can be super annoying and seem obstructive if not handled properly. And the Rebel weakness of disregarding other people’s expectations can be a strength when it is used as a way to break free from disempowering feelings.

The Pros of Being in a Relationship With a Rebel Tendency

After eight months of consistent Oreo eating and Thailand’s higher sugar intake than I was used to took a toll on my oral hygiene. By the time I returned to the states my mouth was probably in bad shape and slowly getting worse.

I didn’t have health insurance, so I put off going to the dentist. Waiting till I could afford it, I made my teeth less of a priority. By the time I finally got dental insurance it had been a year and a half since I had a cleaning.

Naturally, I wasn’t too worried. I had always had healthy teeth and gums. I don’t know if you heard, but at one point in my life I had impeccable oral hygiene.

So when the hygienist told me that I had gingivitis, my stomach plummeted so far south I could have birthed my large intestines. My eardrums started to cloud over and I felt as if I could have been in Garden State.

Gingivitis? What does that mean? I thought.

Luckily, gingivitis is 100% reversible. Apparently I had caught it in time before any bone loss or tooth decay took place. I was fortunate to have come in when I did.

Paying for the treatment — over $200 — I saw it as an investment for self-care. I also made my oral hygiene one of my top priorities and bought an electric toothbrush and a water flosser. I also mouthwash and floss and I chew sugar free gum daily.

Life Application

When I’m feeling like my boyfriend’s Rebel personality is too much to stand, I try to remember the positives—a helpful tip on gratitude for any situation.

Rebels are authentic. They don’t feel the need to meet any kind of expectation from others, which allows them to be free from social constraints that others feel. As a Questioner, I relate to not giving in to peer pressure or the asinine “should”s, however, I do struggle with other "should"s from conditioning as a child and young adult.

My boyfriend has given me permission, multiple times, to release any idea that I need to be a certain way. I have a lot of insecurities from my past that I’ve been able to let go of, thanks to his love and support. He reminds me that I am unique and that is something to appreciate, rather than run away from.

The freedom that Rebels experience and share with others can be extremely helpful for those of us who have needed external approval our whole lives. Throughout the years, I have consistently looked outside of myself for validation and love, and it wasn’t until recently that I have been able to provide myself with what I felt I needed from others.

I think self-confidence naturally grows with maturity and a deeper understanding of life, but it helps to have loving support while navigating these new waters. To be able to depend on someone to be there for you is a freeing and grounding feeling. However, from what I’ve learned about the Rebel Tendency, I wonder if that dependability will be fleeting five years from now.

As a Questioner, I need to be able to have stability. I have so many questions that cause me to spin out and feel overwhelmed easily. Having someone who is steady and reliable can be a source of safety and security for me, and despite his good qualities, I wonder if my Rebel boyfriend has that needed lifeboat quality.

Can a Questioner and Rebel Relationship Last?

This question is something I ask myself constantly. As a Questioner, I am constantly questioning my relationship. Undoubtedly, it is wearing on my boyfriend to always hear my speculations about the longevity of our relationship, and it’s also torture for me not to just enjoy the love.

Each Tendency has their strengths and weaknesses and some may be more compatible than others, but Rubin says that there are so many other layers to someone’s personality than just their Tendency.

Every person is inherently unique due to myriad factors that came together during their time of birth, their upbringing, and any unresolved issues or trauma that prevents them from actually being authentically them. These variables can make each person within the same Tendency behave differently.

Rubin discovered that people have a primary Tendency but also “tip” towards a secondary, which greatly affects their patterns and thought processes. The Four Tendencies tell us about how a person perceives expectations and meets accountability, rather than defining who they are.

So to answer the question about the compatibility of a Questioner/Upholder and Rebel/Obliger (me and my boyfriend), I would say that time will tell. 

As complete opposite types, I struggle to understand his behavior and grasp why he can’t see how damaging his choices are. I don’t dislike the Rebel Tendency when it’s being used in it’s beautiful form of authenticity, rather than disrespectful rebellion, but I wonder about the longevity of an incompatible relationship.

However, my Rebel boyfriend presents a compelling argument—completely in line with his ability to ignore outside pressures or ideas—that it is our choices that matter more. If he chooses to love me, he will, despite all the complications of our opposite types. Again, this is characteristic of the Rebel, they can accomplish whatever they want and choose to do.

The Ultimate Indicator

I guess it comes down to faith. Faith in love, in the communion of two people, and faith that the other person will continue to work on themselves throughout the years as love inevitably shifts in expression and feeling. 

For that is the key; if people are willing to communicate and adapt within the relationship and work together to find harmony, then it is bound to be significantly healthier and more successful of a relationship than more compatible types that don’t communicate or work together.

My Rebel boyfriend is constantly pushing us back to love and communication, he is a pillar of unconditional love and teaches me more everyday, reminding me to open my heart even when it feels vulnerable and scary. 

My Questioner mind goes: Will he always be like this or will he change over time and stop trying? Is it safer to get out now? These questions could be asked of any Tendency, however. For again, it is the strength of a person’s choices and desire to be in a relationship to determine a successful relationship, rather than partial aspects of their personality.

I don’t know what the future holds for my Questioner/Rebel relationship. But I have learned a lot from my Rebel boyfriend and am grateful for Gretchen Rubin’s Four Tendencies so that I can better understand myself and relate to those around me.