Ex-boyfriend, Max, demands ex-girlfriend return all the gifts he gave her, but refuses to tell her why, until their mutual friend discovers he is planning to regift the presents to his new girlfriend: 'I was just trying to help, now everyone is upset'

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Emma Saven
Jul 28, 2025 8:00 PM EDT

It can become difficult to know where your loyalties lie when it comes to being the middleman friend in any off-again-on-again relationship. 

Especially when both friends within the couple look to you for advice and guidance…and even more challenging, when they ask you to keep secrets from their partner. So, how does one decide where the boundaries lie? Does being loyal to one mean being disloyal to another? 

In this story of an on-again-off-again couple, this friend feels conflicted when her best friend's ex confides in her after their short-term friendship remains strong. Although after she discovered that he is seeing a new woman in a matter of days, she feels like she owes it to her best friend to tell her the uncomfortable news. 

What he does to his ex next is even more shocking, and this loyal friend decides she can no longer keep the knowledge of his intentions to herself, causing very mixed reactions from both members of the ever-crumbling relationship…

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  • Heartbreak is a natural part of any breakup, but when a couple begins blaming their friend for making things worse, she finds herself in a moral dilemma, torn between guilt and a deep sense of loyalty to her longtime friend. In the chaotic world of messy breakups, is it nearly impossible to avoid getting caught in the crossfire?

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    "There was a blanket promise over the whole conversation that nothing would be shared with Hailey, but this knowledge was... a lot❞
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    The image does not depict the actual subjects of the story. Subjects are models.

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    AITA for telling my best friend that her ex started dating someone 3 days after they broke up

    Okay, the title kinda says most of it, but basically I have a friend, let's call her Hailey, who got dumped by her boyfriend, Max, a week or so ago. Max and Hailey had a very on-again, off-
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    again relationship, and it's been a few months since it's been any kind of healthy. They were both at fault, and when I learned it had ended, I was sympathetic but unsurprised. Max and I
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    have been friendly for a while, and I've talked him about his relationship with Hailey on several occasions (which she has known about and been okay with) to the point where I considered him to
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    be a friend of mine, especially since his older brother is one of my closest friends. When they broke up, I messaged Max to see how he was doing, and he seemed
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    to be okay. I had no intention to tell Hailey the details of any of our conversations. Then things got weird. Hailey told me that Max had asked for some gifts he had given her about a
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    week before the break-up (nothing expensive or fancy, just some stuffed animals). I asked him why, and he told me he was gifting them to someone else. He had, three days later, started
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    dating another girl and wanted the gifts back to give to her. There was a blanket promise over the whole conversation that nothing would be shared with Hailey, but this knowledge was... a lot.
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    I struggled the whole day and talked to many of my friends and family members (none of whom knew either Max or Hailey except for one mutual friend who doesn't talk to either of them anymore
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    for other reasons). I didn't want to break Max's trust by "telling on him," and I didn't want to break Hailey's trust by keeping something so big from her. That night, Hailey and I Facetimed. She
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    was packing the box of stuff to return to him, and she was wondering why he wanted them back. She made some comments and I couldn't keep it from her. (Hailey has been my close friend for
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    about two years, and Max and I only became friends through their relationship.) I just couldn't lie to her face. Now I'm catching heat from Max. He is very upset with me for telling her. He
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    Cheezburger Image 10534867712
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    The image does not depict the actual subjects of the story. Subjects are models.

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    said that he didn't want her to find out because now she's way more hurt than she was from the initial breakup. I feel because she is in so like such a j much pain now, literally heartbroken, and I broke my trust with Max. I feel so
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    conflicted because I felt so sure in the moment, and now I feel like an a hole. Some of our mutual friends are telling me I should have just minded my own business and kept it to myself, but I wasn't trying to go searching for drama;
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    I was just trying to help, but now everyone is upset, and it's messy. That's pretty much it. Am I the a hle for telling Hailey why he wanted the gifts back, and just in general, he had a new girl?
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    (quick aside, after I told her, she told me that Max had been constantly talking about the girl he's now dating during the last few weeks of their relationship, going as far as to say to Hailey, "she's just like you but with fewer problems.)
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    FacetiousTomato YTA You broke a promise so that you could tell another friend something, when the only outcome would be she is more sad/hurt. How were you "so sure" of that?
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    Possible Pudding_668 OP I guess I was sure because I knew she would be far more hurt if she learned that I kept it from her. I've always been closer to her. She's upset, but at least she doesn't have to deal with a second wave of pain when she finds out later.
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    SunChaserDisc Dyes NTA. Max sounds like he s ks. lol why couldn't he have just bought new stuffies? I'm going to say that your obligation of confidence with him went out the door when he asked you not to spill the beans about him. doing something sh ty to your friend.
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    ScustyRupper BTW-Hailey should put her name on each of the items being returned. Permanent/laundry marker or something even more durable.
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    Green-Device-6064 NTA. You were being a girls girl. You wouldn't be a good close friend if you didn't disclose this. Max should've known better than to tell you anything about Hailey to begin with.
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    West_House_2085 It is absolutely none of your business who either of them date or when! Why did you even consider it your business to tell either of them anything at all about the other person? YTA big time Should'nt have said a d n word!
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that escalated quickly relationship advice gifts secret stuffed animal new girlfriend on and off best friend relationships love-dating group mutuals breakup in the middle return cheezcake dating
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