Should I Refuse to Lend Money to a Friend Who Never Paid Me Back Before?

"Debating whether to lend money to a friend with a history of not repaying loans - setting boundaries or being a supportive friend, what's the right call? AITA?"

It started with a simple loan, then turned into a full-on pattern. A 29-year-old woman, OP, has a friend named Alex who keeps asking for money and keeps disappearing right when repayment time comes.

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We are talking hundreds of dollars across multiple “short-term emergencies,” each with a new excuse. Car trouble, medical bills, unexpected expenses, you name it. OP has been understanding for years, but now Alex is back again asking for a significant amount, claiming it will be temporary, and OP is stuck between feeling cruel for saying no and feeling stupid for saying yes.

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With a decade of friendship behind them and a pile of unpaid IOUs in front of them, OP is wondering if this is still “helping a friend,” or just getting taken for a ride.

Original Post

So I'm (29F) and I have this friend, let's call them Alex. Alex has a history of borrowing money from me and never paying me back.

We're talking hundreds of dollars here. Every time, it's a different excuse - car trouble, medical bills, unexpected expenses.

And every time, I never see that money again. I've tried to be understanding and supportive, but it's starting to feel like I'm being taken advantage of.

Recently, Alex reached out again, asking to borrow a significant amount of money for a 'short-term emergency.' I want to help them out, but I can't ignore the pattern. I feel like if I say no, I'll be abandoning a friend in need.

But if I say yes, I'm setting myself up for disappointment once more. It's a tough spot to be in.

For background, we've been friends for over a decade, and we've had some great times together. But this constant financial strain is putting a strain on our friendship.

I'm torn between being a good friend and setting boundaries for my own well-being. So AITA?

Financial Boundaries

If the friendship is valuable, it's crucial to consider whether you can afford to lose that money without jeopardizing your relationship.

Comment from u/content_craver23

Comment from u/content_craver23
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Comment from u/mystical_soul_94

Comment from u/mystical_soul_94
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Comment from u/coffee_snob_7

Comment from u/coffee_snob_7

Alex’s latest “short-term emergency” request is basically the same song as every other time OP has handed over money and never seen it again.

Ongoing patterns of borrowing and not repaying can signal deeper issues in a friendship.

Comment from u/tech_guru_01

Comment from u/tech_guru_01

Comment from u/plant_lover_56

Comment from u/plant_lover_56

Comment from u/music_junkie_777

Comment from u/music_junkie_777

OP’s decade-long history of great times is what makes the boundary feel so brutal, even when the pattern is screaming red flags.

This also echoes the AITA post where the OP skipped Thanksgiving hosting after a newborn changed everything.

Understanding these underlying issues is vital. By recognizing the emotional aspects of financial transactions, individuals can make more informed decisions about lending. This awareness can lead to healthier interactions and prevent financial disputes in the future.

Comment from u/foodie_for_life

Comment from u/foodie_for_life

Comment from u/beach_bum_22

Comment from u/beach_bum_22

Comment from u/bookworm_1988

Comment from u/bookworm_1988

The comment section keeps circling the same issue, the fact that Alex’s borrowing excuses never line up with actual repayment.

This practice not only formalizes the transaction but also fosters accountability between friends.

Comment from u/gamer_dude_55

Comment from u/gamer_dude_55

By the time OP gets to the point of considering a formal “accountability” approach, it becomes clear this friendship is already strained by money, not just the most recent request.

What would you do in this situation? Share your opinion in the comments.

The dilemma faced by the original poster highlights the intricate balance between friendship and financial responsibility.

This scenario underscores the intricate balance between friendship and financial responsibility. The original poster is caught in a familiar bind where emotional connections complicate the decision to lend money. The tension arises from a desire to support a friend like Ale, who has a history of not repaying loans, against the instinct to safeguard one’s own financial well-being. Open discussions about money can pave the way for healthier interactions, enabling both parties to maintain respect and understanding in their friendship while addressing the realities of lending and borrowing.

Nobody wants to be the friend who funds emergencies that never end.

Before you let guilt win, read how one OP refused Thanksgiving hosting after a family feud.

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