Background: My Ex and I

I (32F) dated my ex “Jake” (35M) for almost four years. Our relationship started fine, but over time, I realized how one-sided and draining it was. Jake was charming in public but careless in private. He often expected me to care for everything — bills, chores, even emotional support — while he coasted through life without much accountability.

I paid most of the rent when we were together because he was always “between jobs.” He’d promise me he was working on getting stable, but nothing ever really changed. I’d come home from work to find him playing video games, while I juggled finances, groceries, and our social life.

Eventually, I realized I was carrying the relationship on my back. I broke up with him almost two years ago, and while it wasn’t easy, it was the best decision I ever made.

How Things Went After the Breakup

After we split, I moved into my apartment and rebuilt my life. I focused on my career, friendships, and hobbies. Jake, on the other hand, seemed to spiral. He moved into a cheap place with roommates, but couldn’t hold down steady work.

Over the past year, I’ve occasionally heard updates about him through mutual friends. Apparently, he burned bridges with his roommates by never paying his share of the bills. He also lost multiple jobs because he “didn’t like the hours” or “couldn’t get along with his boss.”

None of this surprised me. It was the same behavior I dealt with when we were together.

The Current Situation

Now, here’s the problem: Jake reached out to me recently. He told me he’s about to be evicted because he hasn’t been able to keep up with rent. His roommates kicked him out, and he has nowhere to go.

He sent me this long, emotional message about how he’s “struggling,” how “life hasn’t been fair,” and how “nobody cares what happens to him.” He didn’t outright ask to stay with me, but it was heavily implied. He also said things like:

• “I thought you, of all people, would understand.”
• “You know how hard things have been for me.”
• “I have nobody else to turn to.”

My Reaction

I’ll be honest: I didn’t feel sympathy. I didn’t feel bad for him at all.

Why? Because he has always been this way. Jake isn’t a victim of bad luck. He’s a victim of his own choices. He refuses to grow up, take responsibility, and expect other people to rescue him when his laziness and irresponsibility catch up to him

I spent years being his safety net. I spent years carrying him financially and emotionally. And now, after all this time, he’s in the same spot because he never changed.

So when I read his message, my reaction was basically: “That sucks, but it’s not my problem.”

Why I Feel Conflicted

Part of me wonders if that makes me heartless. Homelessness is serious. I wouldn’t wish it on anyone, even someone I dislike.

But at the same time, I can’t ignore the fact that Jake created this situation for himself. He’s not an innocent person who suddenly got hit with tragedy. He had years to get his act together, and he didn’t.

I also don’t think it’s my responsibility to help him just because I used to date him. He’s my ex. We don’t share kids, pets, or property. We broke up for a reason.

What My Friends Say

This is where things get complicated. I’ve shared this with some friends, and the reactions are mixed.

• Some friends said I’m entirely justified. They reminded me of how much I did for him in the past and told me I owe him nothing.
• Others said I should at least show some compassion. They argued that homelessness is a horrible fate, and even if he’s made mistakes, he doesn’t “deserve” to end up on the streets. One even suggested I let him crash on my couch for a week until he figures something out.

Hearing that made me question myself. Am I being too cold?

Why I Can’t Bring Myself to Care

The truth is, I can’t summon sympathy for Jake. When I think about him being evicted, my brain doesn’t say, “Poor Jake.” It says: “Well, what did you expect?”

I watched him waste opportunities. I watched him quit jobs for petty reasons. I watched him live irresponsibly while other people cleaned up his mess. And now, life has finally caught up to him.

If I step in and help him now, won’t that enable the cycle to continue? He’ll learn — once again — that someone will save him, so he never has to change.

My Internal Struggle

Here’s where I feel stuck:

• My head says: He’s not my problem anymore. He dug this hole. He needs to deal with it.
• My heart says: What if he really has nowhere to go? What if he ends up in real danger?

I don’t love him anymore. I don’t even like him. But part of me still remembers the person I used to care about. And that tiny part of me feels guilty for not caring more.

What Jake Wants from Me

Jake hasn’t explicitly asked to stay with me, but I can see where this is going. He keeps dropping hints like, “I just need a place to crash for a while,” and “It’s so hard when no one helps you.”

I’ve ignored those comments so far. I don’t want to say flat-out “you can’t stay here” unless he directly asks, but I also don’t want to leave the door open.

I know that if I let him in, it’ll be a nightmare. He’ll stay longer than promised. He won’t look for a job. He’ll fall right back into old habits. And I’ll resent myself for letting it happen.

The Bigger Picture

This situation made me think about how we handle people from our past. When does compassion cross the line into self-sacrifice? When do we stop being “kind” and start enabling bad behavior?

The line is clear: I can wish Jake well from a distance, but I won’t let him back into my life. I won’t let him drag me down again.

Am I the Asshole?

So here’s my dilemma: AITA for having no sympathy for my ex, who’s about to be homeless?

I feel guilty for not feeling guilty, if that makes sense. But my lack of sympathy is also rooted in reality. Jake’s situation is sad, yes. But it’s also self-inflicted.

I’ve already been his safety net. I’ve already sacrificed my time, money, and peace of mind for him. I don’t want to do it again.

But is it heartless to see someone about to lose their home and feel… nothing?

Reflection: Hard Lessons About Responsibility

This experience has reminded me of a harsh truth: you can’t save someone who doesn’t want to save themselves.

I used to believe Jake would grow up if I gave him enough time, love, and patience. But he didn’t. He only grew more dependent. And now that I’m out of the picture, he’s facing the natural consequences of years of irresponsibility.

Maybe it sounds cold, but I think it’s better for both of us if I keep my distance.

Perfect ✅ Here’s a mock Reddit-style comment section for your post “AITA for Refusing to Pity My Ex Who’s About to Be Homeless?”. I’ve mixed verdicts, tones, and fake upvote counts for realism.

Mock Reddit Comment Section

[NTA] (⬆️ 14.9k)

You’re not responsible for him. Period. He’s a grown man with years to get his life together. Homelessness is sad, but in this case, it’s the direct result of his own choices. You don’t owe him sympathy just because you dated him once.

[NTA] (⬆️ 9.6k)

If you let him stay “for a week,” you’ll have a permanent roommate. People like this don’t change when others keep bailing them out. You’re right — sympathy here would enable the same cycle again.

[ESH] (⬆️ 3.8k)

He’s clearly irresponsible, but you’re being a little cold. You don’t have to house him, but basic human compassion isn’t the same as enabling. You can acknowledge that his situation is bad without taking him back in.

[NTA — Funny Take] (⬆️ 6.2k)

So he wants free rent, food, and emotional labor again? Congrats, he’s trying to reinstall the “Girlfriend 2.0” safety net. Don’t let him. 😂

[YTA] (⬆️ 2.1k)

I know this won’t be popular, but yeah, a little. You don’t have to help him, but bragging that you feel no sympathy makes you sound cold. He’s still a human being, even if he’s lousy.

[NTA and relatable] (⬆️ 4.4k)

I had an ex like this. Always “between jobs,” “down on his luck,” always someone else’s fault. I bailed him out over and over until I finally stopped. Guess what? He figured it out when people stopped saving him. Sometimes letting someone hit rock bottom is the kindest thing.

[NAH] (⬆️ 2.9k)

He’s irresponsible, but being on the verge of homelessness is scary. You’re protecting your peace, which is fair, but don’t feel guilty if you also feel conflicted. It’s natural to feel both.

[NTA — Sarcastic Take] (⬆️ 7.5k)

Yes, the “life is unfair, please rescue me again” speech. Sounds like he’s rehearsed it for years. 🙄 You don’t owe him a single couch cushion.