AITA: My childhood best friends is trans & homeless and I’m tired of helping him?
A childhood best friend is homeless, and the person trying to help is exhausted from carrying the load. The story centers on a transgender (FtM) friend who, years ago, bravely came out and began transitioning, with the poster by their side through every step—from choosing a new name to navigating family rejection. But after a breakup flipped their life upside down, things took a turn.
The friend rejected a rent-free housing offer, opting to live in their car, and keeps asking for money and food despite spending on non-essentials like cigarettes and drugs. What makes this friendship so strained? Alongside the challenges of being transgender, the friend seems to dodge responsibility for their own life.
‘AITA: My childhood best friends is trans & homeless and I’m tired of helping him?’
The story kicks off with a deep bond, where the poster stood by their transgender friend during a life-changing transition.
Everything changed when the friend’s life unraveled after a breakup, and the poster stepped in to help again.
The twist is, the friend made puzzling decisions that pushed the poster into a tough spot.
Eight months later, the friend’s constant reliance is wearing the poster down, emotionally and financially.
How long can a friendship last when one person leans so heavily on the other without standing on their own? The poster’s story highlights a friendship tested by relentless dependency. The transgender friend has faced undeniable hardships—family rejection, a painful breakup, and homelessness. Yet, their choice to turn down stable housing and spend money on cigarettes, drugs, and clothes instead of essentials like hormone therapy points to deeper issues with responsibility and priorities.
The friend’s focus on non-essentials over hormone replacement therapy (HRT)—a critical need—raises red flags. Beyond that, their use of Percocet suggests a potential addiction, which could explain their financial struggles despite a steady job. Dr. Gabor Maté, an expert on addiction, notes, “Addiction is not about the substance but about coping with pain” (In the Realm of Hungry Ghosts). This hints that the friend might be using drugs to numb emotional wounds from their breakup or societal pressures.
Advice: The poster should have an honest conversation, expressing their exhaustion and setting limits on financial and emotional support. Suggest the friend seek therapy or addiction support programs to address potential substance issues. Instead of cash, help with budgeting or connect them to community resources for transgender individuals.
Let’s dive into the reactions from Reddit:
The social media crowd jumped into this story with a mix of empathy, tough love, and a sprinkle of humor, offering varied takes on the situation.
Many users backed the poster, stressing that it’s okay to feel drained when kindness is taken for granted. They urged clear boundaries to protect the friendship.
Some focused on the friend’s Percocet use, warning that enabling could worsen a potential addiction. They suggested helping the friend face their issues head-on.
Others called out the friend for possibly using their transgender identity to guilt-trip the poster into giving money.
A few comments brought levity, pointing out the absurdity of the friend’s spending habits while pleading poverty.
From heartfelt empathy to blunt advice, the community agreed the poster needs to protect themselves while navigating this tricky friendship.
This story is a messy mix of loyalty, tough times, and the strain of one-sided support. The transgender friend is grappling with real challenges—breakups, homelessness, and societal pressures—but their reliance on the poster without taking steps to rebuild has pushed the friendship to a breaking point. The social media community agrees the poster isn’t wrong for feeling drained, though many suggest finding ways to help without enabling.
Have you ever had to set boundaries with a close friend? How do you balance helping someone you care about with protecting your own well-being?
