AITA for confronting my boyfriend about lending his ex money?

A 28-year-old woman has been with her boyfriend for six years and describes their relationship as loving and healthy. However, she recently found out her boyfriend lent $500 to his ex, who cheated on him in the past and occasionally reaches out despite his promises not to engage.

The ex claimed to need money for bills after being disowned and hospitalized for mental health struggles. While her boyfriend insists it was a one-time gesture of compassion with no expectation of repayment,

she feels uneasy about him breaking his promise and helping someone who hurt him before. This led to a confrontation where neither backed down, creating tension. read the original story below…

‘ AITA for confronting my boyfriend about lending his ex money?’

I (F28) have been with my boyfriend (M28) for almost 6 years now. He’s really great — sweet, patient, thoughtful — we rarely fight, and when we do have misunderstandings, we’re quick to sort them out. We also live together and share on the expenses but still have our own separate money.

Now, his ex before me, they were together for about a year right after he started university. They had a pretty toxic relationship, and he had already ended up in trouble academically trying to manage her mental health struggles. He ended things after she cheated on him the second time.

He blocked her at first and did not entertain any attempts to get back together (we were already talking at this point). He unblocked her after a year (he doesn’t like holding grudges). Since then, she’d hit him up on his birthday, Christmas, New Year’s, etc. to send greetings.

She’s gotten bolder since the pandemic, even commenting how happy we (me and my boyfriend) look in our pictures on social. He’d then say thanks or greet back. My boyfriend is very transparent about these things, and I’m generally unbothered.

I did ask him if replying to her, even if dryly, might be doing more harm than good (she might think it’s okay to keep talking to him, which would then be something I WILL be bothered by). He said I was right and promised not to respond at all anymore.

Now, a week ago while we were out, he mentioned how his ex hit him up the day before asking for money. He asked what for, and she said she got kicked out, disowned, and recently landed in the hospital again for mental health troubles and so needed money to pay bills. I thought, well, tough.

I had an ex cheat on me too, and I’m not lending him a dime even if he fell on hard times. My boyfriend doesn’t share the sentiment. He said he lent her money ($500) and isn’t expecting it back. He didn’t open her message explaining what had happened though, nor does he plan to reply.

He just sent her money and that was it. I genuinely didn’t think much of it at the time, but a week later, it was still nagging at me. I think it all boils down to this: it annoys me that he would help someone who once screwed him over and continues to try to be friends with him (?) despite being very clearly in a relationship.

I feel this also breaks his promise of not entertaining anything from her at all, even if he has good intentions. I finally decided to confront my boyfriend about this after he got off work. He said he understands where I’m coming from but that respectfully he can decide what to do with his money.

I told him pretty much everything here, but we ended up at an impasse with neither one backing down. I feel by talking about this, I’ve created some weird tension that neither of us knows how to resolve fully.

There’s just such a huge fundamental difference in how we’d tackle this situation that I also wonder if I’m maybe projecting in some way (?).. AITA? Should I just drop this?

See what others had to share with OP:

ColdstreamCapple −  NTA It’s weird that 6 years down the track she’s still as involved in his life as ever and giving her money is disrespectful to you given he didn’t ask you how you felt on that and just did it…..Yes he may have been transparent to you but it still doesn’t sit right with me.

If she’s as bad as you say she should of been out of his life a long time ago and it sounds like she continues to manipulate him. This would be make or break for me…..If he doesn’t understand what he did was highly inappropriate then maybe it’s time to reevaluate things

cascadia1979 −  NTA. You did nothing wrong in sharing your feelings with him about this toxic ex and his communication with her. He told you he promised not to respond to her any more – but then he not only responds to her, he gives her $500.

While it is his money to do with as he wishes, he also made a commitment to you that he broke.  Your call on how you want to handle this. But handling it by telling him how it made you feel was a healthy response.

Now you have to decide what to do going forward. You could stay with him and forgive him. You could stay with him and attach conditions. Or you could leave him. Any of those would be justified. 

Saberune −  NTA. Giving him the benefit of the doubt, her thinks he’s just being a good friend, but honestly, it’s weird. He had her blocked for as long as they were together. Not exactly friend friends, right? What he’s done is set a precedent. This girl will forever more be the third wheel in your relationship.

He might not be thinking of it that way, but she sure as s**t is. At the bare minimum, she sees him as someone she can use……. just like she did when they were together. He has a right to do what he wants with his money, but you have a right to decide what you’ll put up with from your partner. For me, this would be a dealbreaker.

Pandas-Brat −  NTA. Who gives their ex from 6 years ago, that cheated on them, half a grand… especially without running it by their long term serious partner first ? What the hell.

matthewsmugmanager −  To me, the issue is that you “confronted” him. I would have just asked what he was feeling and why he made that decision. I personally would probably not send money to an ex, but I can, if I work really hard, imagine circumstances in which I might consider it.

So I guess I’m saying you are a little bit of an a**hole for approaching your bf in an accusatory way instead of just asking him about his thought/emotion process.

Individual_Metal_983 −  NTA I can’t fathom why he would send such a significant amount of money to an ex who cheated on him at least twice, with whom he was in a relationship for only a year, 6 years ago and when there are no children involved.

He had even blocked her. And all this when he is in a relationship with someone else. At best it is bizarre and it is certainly a red flag. That he doesn’t see it as such is another one.

love_ci −  YTAH (sorta/kinda?) “Sweet, patient, thoughtful… doesn’t like holding grudges” You know your man, yet are expecting him to act in a way that isn’t him. I don’t see his actions as particularly “entertaining” her, but more of him being the person he is and helping someone who has asked.

He seems like he communicates very openly and doesn’t keep things from you, and because of this, you end up hearing things you might not agree with or like.

esoteriuc −  NTA. I don’t understand why he couldn’t keep her blocked… and why he even cared to unblock her after a year since he’s in a happy relationship and she isn’t in his life. She should be out of sight and out of mind.

Super weird of him to send her the money imo, she isn’t his responsibility and she cheated on him. It’s not like they’re friends.

chocolate_chip_kirsy −  NTA. He said he wouldn’t be in contact with her, and he not only responded, but he gave her money. He lied. You have a right to be angry. I feel like his comment about deciding what to do with his money speaks to the likelihood that he’ll do it again regardless of how it makes you feel.

sadilady18 −  NTA- he said it’s his money after 6 years and sharing a life together supposedly. I’m guessing you have no plans of being a fiancé or wife, and you got told that as a girlfriend larger sums weren’t going to be your concern. So, you have to decide if you are ok with there not being an “ours” or limits on large financial purchases.

Is she justified in feeling unsettled, or should her boyfriend’s good intentions outweigh the concerns? What would you do in her situation? Share your thoughts below!