Today’s Read: 7 Minutes

This was supposed to be a piece about a completely different topic but here I am doing my first-ever honest reflection on my dating life.

So how did we get here?

Maybe it’s been the steady drumbeat of weddings I’ve been attending. Maybe it’s the first hint of Spring arriving in New York. Maybe it’s my parents’ lighthearted jokes about how long I’ve been single now slowly evolving into genuine concern.

As you know, I’ve been working on becoming more self-aware and emotionally resilient. But I realized that this journey feels incomplete without understanding this critical aspect of our lives. After all, our romantic relationships elicit so much genuine happiness and fulfillment when they’re going well and so much heartache and insecurity when they’re not.

Romantic relationships aren’t an easy topic to write about and I’m especially sensitive to how being a single, twenty-something male can cast an unfavorable shadow on what I’m about to say. Pile on the simple fact that I’ve neither prioritized nor been particularly intentional about my dating life and we have a perfect storm of me being out of my depth.

What is pushing me forward is a recent revelation that none of the things I care about—my mental health, my friendships, my career, my interests, and, more recently, my past and future romantic relationships—can be compartmentalized.

They’re all driven by the same underlying set of fears and insecurities even though they manifest themselves differently in their respective contexts.

It’s worth reflecting on how I’ve handled previous romantic relationships, the psychology that motivated these behaviors, and what I hope to work on in the future.

So here I am, sipping a glass of whiskey, listening to Death Cab for Cutie, and trying to examine my own psychology through a lens I’ve been previously neglecting.

I’m hopeful that this gives me a fresh outlook on not just how I approach relationships but how I can continue my emotional fitness journey moving forward.

Previous relationships

Don’t worry, I have no intentions of doing a lengthy postmortem of each romantic relationship. I’ll spare you my rendition of To All the Boys I’ve Loved Before and just say that there’ve been some really beautiful moments, some really awful memories, and some hilariously embarrassing episodes punctuated throughout.

All of these experiences provided unique and valuable lessons, but after learning more about romantic attachment styles, I realized that they all shared similar patterns.

For the uninitiated, there are classically four types of romantic attachment styles:

* Anxious attachment

* Avoidant attachment

* Fearful-avoidant attachment

* Secure attachment

With the heavy caveat that attachment styles change depending on the relationship and context, I’ve historically exhibited anxious attachment tendencies.

People with this attachment style have a strong desire for emotional closeness but fear abandonment. We’re comfortable sharing our genuine feelings of affection but bottle up any negative emotions for fear that they can cause conflict. This often means that we’re highly attuned to what our partners need, but oftentimes don’t consider our own.

Left unchecked, those with anxious attachments turn their partner’s affection into an addictive form of external validation. Their affection becomes the primary focus rather than the overall health of the relationship itself.

I still cringe remembering a time when I skipped class to buy an ex-girlfriend’s favorite cookies thinking those sorts of heroics could fix a relationship that was well past its expiration date.

We broke up a few days later.

When our partners start pulling away and we’re no longer getting that steady dopamine hit of devotion, the confidence and independence we’ve so carefully cultivated can quickly turn into crippling anxiety.

Almost like an addict going through withdrawal, our behavior can change dramatically.

For me, signs of trouble cause me to completely shut down emotionally. I tell myself (and regrettably even my partner sometimes) how meaningless the relationship is to me. I build up a wall and attack first before this hollowing sense of being abandoned can land its punches. I’ve pushed partners away with measured indifference while secretly hoping they’ll still want to stick around even after I scorch the earth.

I haven’t been in a genuinely serious relationship for close to two years now and I thought I had worked through a lot of these demons.

Naively, I thought the solution was to skew more towards emotional unavailability, adopting some of the same stereotypical tendencies single folks in New York exhibit: frequent dating but short-lived relationships, matching the city’s bustling activity with a similarly fast-paced approach to dating.

But I was still focusing intensely on whether the person across from me was having a good time without a single consideration for what I actually thought of them. I was hyper-attuned to displays of affection just like I would in a more serious relationship, except things were still too early stage for the emotional stakes to feel substantial.

Instead, the first few awkward dates feel like a dopamine-seeking game of collecting as much affection as I can.

Courting in the early stages of casual relationships reminded me of comedians workshopping new material at a local comedy cellar. As if dating was some sort of craft that can be honed, I was constantly fine-tuning the right stories, the right compliments, and the right romantic gestures in order to maximize the perception I held in their eyes.

To be fair, I’ve had more than my fair share of bombs and getting boo’ed off stage. Except comedians were practicing for a big upcoming show whereas I was…I don’t even know.

Do this long enough and dating just becomes a soulless routine, exacerbated by the convenience of dating apps and a city full of incredibly interesting and attractive people.

The curse of variety and availability is that dating can be fun but can ultimately feel hollow and unfulfilling.

Finally, a girl I was seeing had the courage to snap me out of my pernicious state of autopilot when she told me, “Why does it always feel like you’re performing whenever we’re together?”

Here I was, thinking that I was a far more emotionally balanced romantic partner than the one who exhibited anxious attachment tendencies when in reality the same lingering insecurity hadn’t been addressed at all.

I still had this long-held, subconscious belief that I wasn’t worthy of feeling good about myself until someone could bestow that esteem upon me.

And that sparked some critical self-reflection.

Where did this self-serving need for affection come from?

My psychology

Growing up, I idolized smooth-talking TV characters like Will Smith in Fresh Prince of Bel-Air just like I idolized athletic heroes like Kobe Bryant. I assigned an aspirational amount of value to men who seemed like they could always find the right words to say and push all the right buttons to win over someone.

Just like I needed good grades and awards to feel smart and capable, I pursued romantic partners in order to feel strong, interesting, and attractive.

I craved affection just like I craved athletic, academic, and career success, treating the general topic of romantic relationships like some challenging mountain that I can climb in order to achieve some higher-order state of happiness.

It’s also why I’ve caught myself drawn to those who were more emotionally distant.

When you spend more of your life striving towards that next achievement, it’s easy to convince yourself that things are inherently more valuable when you have to work harder for them.

And despite knowing that inconsistent, hot-then-cold behavior exacerbates my anxious attachment style, I subconsciously thought affection was somehow more valuable if it didn’t come easily.

Rather than working on my self-esteem, communicating with my partner, or just acknowledging that a relationship isn’t good for either of us, I’d exhibit the same patterns of trying to win over someone’s devotion.

Dating turned into some superficial bandage over a wounded sense of worthiness, a distraction from actually working on my own sense of self-worth.

Everything—from the pressure I put on myself to succeed in my career, to the nagging feeling that I’m not good enough, and this recent realization that I’ve had an unhealthy need for romantic affection—all stems from attaching my own worthiness to others’ perceptions of me.

I never actually learned how to define my own sense of worth.

What I hope to work on

I’m grateful for the heartfelt conversations that have guided me over the past few months. Addressing these tendencies is still very much a work in progress, but I’ve narrowed down a CVS receipt length of action items into a few things that are top-of-mind for me in the near term.

* Focusing on connection: It hurts to admit how I’ve been consistently writing about being more intentional and yet I haven’t done it at all when it comes to romantic relationships. Dates can easily feel like some sort of performance rather than an opportunity to actually get to know the person I’m trying to build a connection with. Am I excited to be around them? Do they inspire me? Am I happier with them? These are shockingly simple questions that I’ll need to ask myself more often.

* Communicating my needs: Exhibiting insecure attachment means we maintain this fear that our partners will leave at the first sign of trouble. Relationships can feel brittle, so we paper over problems, ignore red flags, and suppress any feelings of uneasiness to avoid any sort of conflict. I’m learning to actually identify and communicate what I need from a relationship. It doesn’t mean that I suddenly start keeping score and making things all about me—I believe the healthiest partners figure out what’s best for the relationships rather than framing everything as my needs vs. theirs. Instead, it’s not letting fear stop me from asking: “How are things going?”, “What doesn’t feel right?” and “What do we need to address?”

* Defining my own self-worth: This last one is probably the most important because it transcends every aspect of my life. While our flaws and shortcomings always feel glaringly obvious during any self-improvement journey, I’m reminding myself that you don’t need to be at some upper echelon of attractiveness, intelligence, and success to deserve love, happiness, and self-esteem. And at the risk of sounding like a self-help cliche: we’re ultimately the ones who define our own worthiness.

And if these takeaways feel redundant, it’s probably because it jives with a lot of what I’ve been working through in my writing:

* Being intentional about our time and energy

* Better understanding and communicating my own thoughts and feelings

* Focusing on internal motivators rather than seeking external validation

For me, being kinder to myself is learning to accept that I’ll continuously strive towards becoming a better human but that my sense of self-worth is not gated by others’ opinions of me.

As a lifelong people-pleaser, I know that there’s still a lot of progress to be made and that I won’t flip this switch overnight.

But I’m excited to do this work because I’m convinced it’ll not only improve how I’ve approached relationships but all other aspects of my life as well.

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