The Unpleasables
When Love Is a Moving Target
I am going to breakdown how to navigate relationships with those who give with strings attached, expect emotional ROI, and struggle to meet their own needs.
We all have them.
That person in the family who keeps the group chat alive with drama, guilt, or passive-aggressive jabs. Or maybe they show up with baked goods, unsolicited advice, or emotional monologues—but always seem upset no one’s clapped loud enough. They give, yes—but not without keeping score. And somehow, they’re still the victim in the end.
Meet the Unpleasables.
These are the folks you care about, maybe even love deeply, but consistently feel like you’re walking on emotional eggshells around. They’re not outright toxic—but they’re exhausting. They give, but they give in a way that feels more like a trade deal wrapped in obligation and expectation.
And here’s the kicker: They usually don’t meet their own needs, so they end up placing the burden of emotional fulfillment on others—often unconsciously.
Who Are the Unpleasables?
Unpleasables are not narcissists. They’re not evil. They’re not monsters.
In fact, they’re often the most self-sacrificing people you know. They’ll bend over backwards, say yes to things they don’t want to do, and claim they’re “just trying to help.”
But their help often comes with a side of guilt, resentment, or emotional blowback when things don’t go the way they imagined.
They operate on a kind of covert arrangement:
“I’ll give to you in the ways I think are meaningful, and in return, you’ll give me the emotional payoff I didn’t ask for out loud—but really needed."
Their behavior isn’t malicious—it’s patterned.
Most Unpleasables were raised in emotionally chaotic, needy, or immature households. They may have had to over-function as children, taking care of a parent’s emotional state, walking on eggshells, or managing the feelings of those around them.
In short, they learned early: If I’m useful, I’m safe.
Why They're So Hard to Deal With
Because they don’t know they’re doing it.
And because we want to love them.
We want to stay connected.
They’re often parents, siblings, adult children, or long-time friends. Cutting them off entirely may not be an option—nor does it need to be.
But staying in connection requires a different set of emotional tools.
Unpleasables tend to:
Struggle with boundary clarity (and get hurt when you set one)
Expect unspoken emotional payback for their efforts
See their identity as tied to how much they do for others
Feel chronically unseen or underappreciated
React with anger, hurt, or guilt-tripping when they feel disregarded
Rarely tend to their own emotional needs in healthy ways
Their giving becomes their identity. But it’s a codependent identity—one that requires others to respond a certain way in order for them to feel okay about themselves.
And when that doesn’t happen, they unravel.
Where This Comes From…
This pattern almost always has roots in early emotional dynamics:
Emotionally immature parents: The child becomes the emotional regulator or peacemaker.
Volatile or needy caregivers: Love becomes conditional, based on usefulness or compliance.
Unresolved generational trauma: Guilt, obligation, and performance get passed down like family heirlooms.
Cultural narratives: Many cultures reinforce duty, sacrifice, and “good child” roles at the expense of personal boundaries or individual emotional health.
Add in historical trauma, enmeshment, and learned helplessness, and you’ve got a recipe for a person who struggles to separate giving from being worthy of love.
So What Can You Do?
Let’s be real: You’re probably not going to have a calm, tearful breakthrough moment with an Unpleasable that ends in mutual understanding and a new family ritual. But you can:
1. Stop trying to please the unpleasable.
It’s not your job to heal their unmet emotional needs. If you keep over-giving to avoid their reactions, you’re reinforcing the pattern. Plus, they will never ever even begin to contemplate meeting their own needs through other options! (Friends and hobbies)
2. Set boundaries with emotional neutrality.
Don’t over-explain. Don’t justify. Just state your limits and follow through with calm consistency. Expect pushback—see it as proof the boundary was needed. A tone of indifference and positively labeling them as trying to be loving may be helpful.
3. Acknowledge their effort—without feeding the dynamic.
You can say, “Thanks, that was thoughtful,” without letting guilt dictate your next 10 moves. Validation doesn’t mean compliance and that you signed up for their covert arrangement!
4. Shift from guilt to grief.
You can’t be who they want you to be. You’re not responsible for their unmet childhood needs. That’s not mean—it’s maturity. Let yourself grieve that the relationship may never feel fully mutual.
***You may also want to start meeting the majority of your own needs too. More often than not people who are struggling with detaching also tend to be a lite version of the unpleasables…(More on this tomorrow!)***
5. Don’t try to win the emotional tug-of-war.
The more you defend, justify, or explain, the more enmeshed you get. Sometimes, the most powerful move is silence, followed by a change in behavior—not a change in argument.
6. Create micro-boundaries around time, energy, and conversations.
Don’t stay on the phone for an hour out of guilt. Don’t engage in emotional dump sessions you didn’t agree to. Protect your bandwidth.
Your emotions and choices your responsibility and vice versa.
Bottom Line
You can love someone deeply without being responsible for their emotional balance.
You can have compassion without collapsing into their covert agreement.
And you can stay in connection without sacrificing your own peace.
The Unpleasables don’t need to be cut off—but they do need to be related to differently.
Because if you keep trying to play their emotional game, you’ll always lose.
Not because you’re failing them—but because their scoreboard is rigged.
Stay tuned! More on the unpleasables tomorrow!
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