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Her Boyfriend Slept With Her Best Friend Several Times Before They Began Dating, And They Chose To Hide It From Her

profile Bre Avery Zacharski | May 4, 2026
May 4, 2026
Friendly portrait of a smiling young woman
puhimec - stock.adobe.com - illustrative purposes only, not the actual person

It’s bad enough when someone you love withholds important information from you, but you know what’s even worse? When two people you’re extremely close to decide to keep a secret, and you’re the odd one out.

This 33-year-old woman has spent years being friends with her 33-year-old female bestie and her 36-year-old boyfriend. She’s actually been dating her boyfriend on and off for the last two years, but eight months ago, they made things official again and have been going strong ever since.

Her boyfriend has always been kind to her friends, but in the last three months, he and her bestie have become basically glued at the hip. Her boyfriend and best friend talk nonstop, and deep down, she found it suspicious.

“I had a gut feeling a month ago and asked my boyfriend if they had hooked up in the past. He was honest and said they had. And it wasn’t just once,” she explained.

“It was before [he] and I were together. I just can’t help but feel like they both talked and agreed not to tell me. They’ve been friends all these years, too. I am so thankful he was honest, of course. But now I just feel literally icky?”

“Like, why didn’t my best friend mention this when she was having all these heart-to-hearts with me? Why didn’t he mention it when he saw us becoming close? I want to be with him, and I want to be friends with her. But I can’t help when we all hang out thinking about them hooking up.”

Earlier today, she confronted her bestie and let her know that she’s aware of the hookups. Apparently, her best friend then told her that she had privately questioned her boyfriend a week ago about whether she knew about the two of them, and her boyfriend had said yes.

Her boyfriend never mentioned that to her, although he knows how she’s been having a hard time coming to terms with the two of them hiding such a big secret from her.

It’s really upsetting to her that her boyfriend and best friend had a side conversation about her, and nobody thought to include her.

Friendly portrait of a smiling young woman by modern stairs, soft light highlights natural beauty. Ideal for personal branding and headshot use.
puhimec – stock.adobe.com – illustrative purposes only, not the actual person

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“So I feel dumb. How do I move on? I just don’t think he’d be comfortable if roles were reversed. But they aren’t reversed. This is my unfortunate reality,” she continued.

“I wish I never found out. Truly. My heart feels sick and broken. But I want to move on and get over it. Any tips on how to move forward?”

The only way for her to move on is without her boyfriend and her best friend, because they both betrayed her. And also, the fact that her boyfriend and best friend have gotten even closer throughout the last three months is really weird.

It seems like they still could be hooking up!

What advice do you have for her?

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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