Dealing with a Freeloading Friend: Setting Boundaries on Borrowing Money
Struggling with a friend who always borrows money but never pays back - contemplating setting boundaries to protect financial and emotional well-being, seeking advice.
It started with a simple loan, and it somehow turned into a full-blown financial headache for a 29-year-old woman and her family friend, Sarah. For years, Sarah would pop up with “small” requests, promising she’d pay it back soon, then follow up with delays, excuses, and silence.
Recently, Sarah asked for a significant sum to cover unexpected bills. OP hesitated, but agreed because they’ve known each other since high school. Then the weeks rolled by, the repayment never showed up, and when OP finally brought it up, Sarah got defensive and claimed she was having a rough time.
The part that really broke the trust? OP saw Sarah posting about shopping sprees and dining out while still dodging the money she owed.
Original Post
So I'm (29F) in a bit of a pickle with a family friend, let's call her Sarah. Sarah and I have known each other since high school, and she's always been the type to ask for small loans here and there, promising to pay me back soon.
But the thing is, she never does. It's always some excuse or delay, and the money never comes back.
For background, Sarah recently hit me up asking for a significant sum of money to cover some unexpected bills. I was hesitant but agreed out of our long history.
However, weeks have passed, and she hasn't made any effort to repay me. When I brought it up, she got defensive, saying she was going through a rough time.
The breaking point was when I saw her post on social media about shopping sprees and dining out, which made me question her sincerity in repaying me. I'm frustrated and feeling taken advantage of, so I've been avoiding her calls and messages.
I know she's a family friend, but her behavior is straining our relationship and my finances. So, would I be the a*****e for keeping my distance and not lending her any more money in the future?
Really need outside perspective.
This proactive approach can prevent feelings of resentment and ensure that both friends maintain their relationship while protecting their financial stability.
Comment from u/PancakesAndCoffee

Comment from u/gamer_gal2000

Comment from u/luvbug_47
That “soon” never arrived, even after OP kept bringing up the loan with Sarah and watching her brush it off.
When Sarah asked for a bigger amount to cover unexpected bills, OP tried to give her the benefit of the doubt.
It’s a lot like the AITA about supporting her sister’s risky career change, even when finances are the real stressor.
This can involve asking open-ended questions like, 'How do you plan to pay me back?' to gain clarity.
Comment from u/glee_fanatic
Comment from u/stormborn_bard
Then OP saw the social media shopping sprees and restaurant posts, and suddenly Sarah’s “rough time” story didn’t add up.
Now OP is avoiding Sarah’s calls and messages, and the family-friend bond is getting stretched to the breaking point.
How would you handle this situation? Let us know in the comments.
The situation faced by the Reddit user illustrates the intricate dance of kindness and boundaries that often arises in friendships, particularly when money is involved. The case of Sarah and her friend underscores the need for honesty and transparency when it comes to financial matters. By engaging in open communication about borrowing, the Reddit user can navigate this challenge without jeopardizing the friendship. The article highlights that approaching the subject with kindness and understanding is key to preserving not only the relationship but also one's financial well-being. This situation serves as a reminder that implementing such strategies can lead to more balanced and respectful interactions, ultimately benefiting both parties involved.
It sounds like this friendship is caught in a classic case of boundary issues and the emotional toll that can come from financial dependency. The frustration OP feels likely stems from a mix of betrayal and the realization that her kindness is being taken for granted, which can lead to resentment. Setting boundaries isn’t just about protecting finances—it’s also about reclaiming emotional space and fostering healthier, more respectful relationships.
Nobody wants to keep funding Sarah’s dining out while she treats repayment like optional homework.
Want another boundary showdown, read whether she should skip her sister’s wedding over Chris’s disrespectful behavior.