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He Called Off His Wedding And Is Considering Ending His Engagement After Finding Out That His Brother Used To Sleep With His Fiancée

profile Bre Avery Zacharski | Jun 26, 2026
Jun 26, 2026
Girl with long red hair.
alenazamotaeva - stock.adobe.com - illustrative purposes only, not the actual person

It is so gross when a sibling decides to go after their brother or sister’s ex, because that’s the definition of sloppy seconds. How would you feel if you found out that the person you were about to marry used to hook up with your sibling? Would that make you call off the wedding?

Back when this 27-year-old man was 15, he started dating his 27-year-old fiancée, so they are truly high school sweethearts, as well as one another’s first experiences in love.

They had made plans to go to the same exact college after graduating, but he got accepted at the last minute to the school of his dreams after being placed on a waitlist. He ultimately picked that college over his original choice, which really upset his fiancée.

She was actually so mad that they broke up for that reason as their senior year of high school came to an end. They did split on good terms and went their separate ways.

“We ended up not speaking for the entire time we were at college. Fast forward about 6 years, and we ended up in the same city when we were about 24. She reached out first, and we ended up catching up and decided to give us another try,” he explained.

“We had both grown a lot as people, and our relationship was a lot different than when [we were] teenagers, but we still had a similar spark.”

Three years ago, they officially started dating again, and he proposed two months ago. He was elated when his fiancée said yes to being his wife, and they wasted no time getting down to planning their wedding.

Over the last two weeks, though, his fiancée has not been herself and has seemed hesitant about their upcoming wedding and marriage.

“Then last night, she sat me down and said she needed to tell me something that’s been eating at her for a long time. She confessed that during college, she had a year-long friends-with-benefits situation with my older brother (30m),” he said.

Girl with long red hair.
alenazamotaeva – stock.adobe.com – illustrative purposes only, not the actual person

“It was when she was about 19, and my brother was 22, so about a year after we had broken up. My brother had graduated and started his first job in the same city [where] she was studying, and since he didn’t know anyone else there, they began hanging out.”

“Apparently, they had gotten really close and eventually started sleeping together. They kept it up for about the entire school year until she went back home for the summer, and by the time she had come back, my brother started working somewhere else.”

His fiancée insisted that her relationship with his brother was meaningless and just came down to them both feeling incredibly lonely.

She also said that she was not in a good place following their breakup and did not fall in love with his brother or anything like that.

He’s so close to his brother, which made the news even more damaging. His brother has never alluded to hooking up with his fiancée, and at one point lied to him and said he had never run into his fiancée in the city where they both had lived.

His fiancée has spent a ton of time with his family and his brother after reconnecting, so that makes it even worse to him that they both had countless interactions and kept their relationship a secret from him.

“My brother was even so excited for us when we announced our engagement, and I just feel so betrayed knowing that they were keeping this from me for so long,” he added.

“She said that she couldn’t go into our marriage keeping this secret, and that she needed to get it off her chest. She reiterated that nothing [has] happened since that summer and even offered to let me go through her phone to check for myself.”

“I don’t even know what to think at this point. My brother is married and has been for the last 2 years, so I somewhat believe her when she says nothing more happened. But at the same time, if she could keep this from me for so long, I don’t know what else she could be lying about.’

“I went really quiet after she told me all this, and she asked repeatedly what I was thinking and if I was gonna say anything, and I just told her that I don’t think we should be getting married right now. I didn’t break up with her outright, but I can’t just pretend to be okay and go through with marrying her while all this is on my mind.”

His fiancée was extremely upset over his decision to call off the wedding and potentially end their engagement. She keeps insisting the relationship with his brother did not mean anything to her, but that’s not helping.

He has not talked to his fiancée since then, and he did see her crying in their bathroom earlier this morning. He hasn’t had a chance to speak to his brother, but he is going to.

He doesn’t think his brother is innocent, and he keeps thinking about how his brother hid the truth from him for so many years.

While yes, his brother and fiancée being a thing happened a long time ago, and he was officially broken up with her, it’s just not something he can get over.

“I just don’t know how to navigate all this and don’t know if this is even salvageable, and I definitely don’t think I’m ready to marry her right now,” he concluded.

His brother and his fiancée are truly horrible and repulsive for hooking up with one another and then not telling him about it. I would not marry this woman if I were in his shoes, because he’s right; what else could she be hiding from him?

And while this is water under the bridge and old news to his fiancée, this is a fresh wound to him, and it’s not cool that she’s not understanding that or giving him space to sort through his emotions.

If he has any desire to salvage his engagement, I do think he should tell his fiancée she has to go to couples counseling with him, as this is too big to work through alone.

Do you think he should leave his fiancée?

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By Bre Avery Zacharski

Hi, I'm Bre, Chip Chick's CEO! I have a degree in Textile/Surface Design from The Fashion Institute of Technology, and... More about Bre Avery Zacharski