When It Hurts So Bad, Why Does It Feel So Good?

The addictive pain of wanting what we can't have.

I’ve been thinking a lot about guilty pleasures lately and i’ll be the first to admit I have quite a few, and I’m sure you do too.

Whether it’s overconsumption, procrastination, the lure of a passionate but unraveling entanglement, or the harmless-seeming white lie told without cause— there’s an undeniable allure to self-sabotage. These impulses, indulgences, and small betrayals hold a strange gravity. We know better, often, but knowing isn't always enough.

There’s something irresistibly human in indulging in what’s clearly not good for us.

When thinking about guilty pleasures, I can’t help but to reflect on the generation that came before us— their pleasures were and are fairly modest: a quiet backyard, a stable paycheck, the comfort and familiarity of routine. They moved through a kind of quiet gold rush era in the United States, not of riches unearthed from the ground but of opportunity seamlessly embedded in the everyday. They do not apologize for their contentment because it was hard-earned within a system that seemed to keep its promises.

They were sold a dream — homeownership, a nuclear family, retirement by sixty — and remarkably, though not without effort, they moved through life with the quiet assurance that their labor would be rewarded. They lived by a blueprint we’re still expected to follow, even as its foundations have long since cracked.

We inherited the illusion, but not the conditions that made it possible. And in the absence of that promise, many have drifted, jaded, overstimulated, seeking comfort in small excesses and fleeting indulgences.

Nevertheless, this isn’t a story about the collapse of the American Dream. It’s about the human desire to wants things that aren’t in our best interests.

When I think about this “guilty pleasure” pain/pleasure paradox, I’m primarily fixed on relationships—platonic, romantic, familial.

If you’ve dated into your 30s, I can almost guarantee you’ve found yourself on both sides of the spectrum.

On one side: you’ll chase someone who only ever runs. They don’t want a future with you, just a warm body on a Friday night and the ego boost of your devotion on a Monday morning. So you perform, pirouetting through their imagined fantasies, hoping your perfect act will finally make them see you as more than just an intermission between lovers.

On the other side: you are the one being chased. You say no—politely, then firmly, then with a tinge of exasperation. But still, they linger like a song stuck on repeat, refusing to hear the silence between your words. And you find yourself wondering: Is unrequited love still romantic when you’re the one being cornered by it?

Yet, it all boils down to the same thing, we are conditioned to desire things which are intrinsically more difficult and/or painful to obtain.

For example, when coveting friendship, you’ll buy similar outfits or go to the same establishments, even curate your socials just to get the cool girls to notice you. All without thinking about if the friendship would actually be worthwhile.

With family, (especially if you’re the youngest) you will silence your opinions in order to be allowed to stay in the room. You’ll apologize for everything on behalf of everyone just to find peace with the people you love. And still, an older sibling or parent will inevitably find a way to make you feel insignificant, as if you’re desire for relationship is rooted in something other than pure love.

What if Lauryn Hill wasn’t being poetic, but prophetic? “When it hurts so bad, why does it feel so good?” — not just a lament, but a warning.

A whisper to pay attention.

Why are we so tethered to what diminishes us?

We remain entangled in friendships defined more by performance than reciprocity.

We shape-shift to preserve peace in families while the person causing the chaos continues to break everyone’s heart with little remorse.

We label our habits “guilty pleasures,” though many are neither pleasurable nor harmless, just practiced forms of avoidance dressed as indulgence.

There is a difference between comfort and sedation, between connection and compliance and between desire and compulsion.

But when pain becomes familiar, it’s easy to mistake it for a deeper meaning. We’re more liable to return to the same dynamics, habits, distractions and not because they serve us but because they’re known. We know that if we pursue the thing head on, we feel like we’ve done our best, we can blame the other, but that is a fallacy that must end in order to grow.

The rituals we repeat—emotional, relational, behavioral—are rarely random. We reenact what we believe we’re worthy of. We chase the approval, closeness, and relief in places that have never truly offered them.

I talk about this not as some self-help jargon, but as a self-aware adult.

The work, if there is any, is not to seek more of what feels good or crucify oneself for the sake of peace but to interrogate why so much of what we call “pleasure” depends on our own self-sabotage.

Perhaps, that’s the only way we can finally understand how the things not meant for us will not become through sheer effort alone.