Man Decides to Date His Longtime Friend Only to Incur Expenses, Finally Decides to Let Her Be Homeless

"She’s upset that it isn’t happening fast enough for her"

A 28-year-old woman refused to get her life together, and the man trying to help her ended up wondering if he made things worse instead of better.

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It started with a longtime friendship that had a financial side to it, and then turned into something messier when she struggled to find and keep a place for months at a time. She had a compromised immune system, so OP wasn’t trying to punish her for being sick, but the pattern kept stacking up: a coffee shop situation where she needed a leave of absence, living with a coworker only until the end of the month, and then the looming threat of being homeless.

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What finally pushed OP over the edge was the way he felt stuck paying the price while she kept moving the goalposts.

OP's Girlfriend Has a Hard Time Finding and Keeping a Residence for Long Periods of Time

OP's Girlfriend Has a Hard Time Finding and Keeping a Residence for Long Periods of TimeReddit/Chenzo55BETA
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She Suffers from a Compromised Immune System, So the OP Wasn’t Going to Hold That Against Her

She Suffers from a Compromised Immune System, So the OP Wasn’t Going to Hold That Against HerReddit/Chenzo55BETA
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Friendship and Financial Responsibility

In friendships, particularly those that involve financial interdependence, expectations can become tangled.

The Coffee Shop Demands She Take a Leave of Absence for Some Reason

The Coffee Shop Demands She Take a Leave of Absence for Some ReasonReddit/Chenzo55BETA

She Is Living with a Coworker Until the End of the Month and Will Be Homeless Afterward

She Is Living with a Coworker Until the End of the Month and Will Be Homeless AfterwardReddit/Chenzo55BETA

OP thought he was dating a “friend who needs help,” but the second the coffee shop demanded a leave of absence, it was clear the timeline was getting dangerous fast.

OP Has Offered the Following Explanation for Why They Think They Might Be the A-Hole:

I feel that I am the AH for not just getting a place to rent with her and effectively giving up on getting a house.

The Reddit Post Received More Than a Thousand Comments, and We've Gathered Some of the Most Upvoted Ones for You to Check Out Below

The Reddit Post Received More Than a Thousand Comments, and We've Gathered Some of the Most Upvoted Ones for You to Check Out BelowReddit/Chenzo55BETA

She Is Beyond the Point of Trying to Choose

She Is Beyond the Point of Trying to ChooseReddit/Chenzo55BETA

When she said she’d be homeless after the month ended and was only staying with a coworker for now, OP’s “we’ll figure it out” plan started sounding like a bill he never agreed to.

This is messy like the rent-versus-gambling fight, where Reddit debates whether to refuse lending money to a friend.

Psychologically, the decision to allow a friend to be homeless can evoke feelings of guilt and obligation.

She Is Stringing the OP Along with Her Mess

She Is Stringing the OP Along with Her MessReddit/Chenzo55BETA

Why Does She Have a Problem Holding Down Jobs?

Why Does She Have a Problem Holding Down Jobs?Reddit/Chenzo55BETA

The comments basically zeroed in on one fear, if OP buys a house and moves in, his longtime friend might never actually stop needing a new place.

Establishing Healthy Boundaries

Setting healthy boundaries is essential in any relationship, especially when financial issues are involved.

Practices such as defining financial contributions and expectations can help prevent feelings of resentment. Engaging in open discussions about financial roles can create a stronger foundation for the friendship.

OP's Girlfriend Is Irrational, Irresponsible, and Entitled

OP's Girlfriend Is Irrational, Irresponsible, and EntitledReddit/Chenzo55BETA

This Redditor Insists That Dating Homeless People Is Great

This Redditor Insists That Dating Homeless People Is GreatReddit/Chenzo55BETA

Now OP is stuck asking whether he’s the A-hole for offering boundaries, instead of just swallowing the costs and hoping she finally lands somewhere stable.

Redditors were of the opinion that OP's girlfriend is careless and that she might never leave if the OP ever purchases a home and moves in with her! Depending on the laws of the state where the OP resides, he may always be the one to keep saving her.

The OP's Crush on Her Is Being Exploited

The OP's Crush on Her Is Being ExploitedReddit/Chenzo55BETA

Does She Ever Show the OP Proof That She Is Indeed Working?

Does She Ever Show the OP Proof That She Is Indeed Working?Reddit/Chenzo55BETA

The narrative of a man deciding to date his longtime friend brings to light the intricate balance between emotional connections and financial responsibilities. As the story unfolds, it becomes apparent that the transition from friendship to romance is fraught with challenges, particularly when monetary concerns enter the equation. The man's eventual choice to let his friend face homelessness illustrates a stark failure in establishing boundaries and expectations that are crucial for a healthy relationship.

Open communication is vital in navigating such complexities, yet this tale highlights how easily misunderstandings can arise. The financial strain and the resulting conflict demonstrate that love is not merely about affection; it also involves managing practical realities that can threaten the very foundation of a relationship.

He might be the problem, but nobody wants to bankroll a homelessness countdown.

Before you judge the “date her, then foot the bill” move, read whether OP should deny a loan after a friend failed to repay.

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