A proposal is supposed to be a vow for the future, but for these high school sweethearts, it became sullied by a confession from the past. Just seven days after sliding a ring onto his fiancée’s finger, she confessed to cheating on him, and with her boss, no less.
He still wants to fight to save their relationship, but is he simply the stability she chose once her first choice at the office didn’t pan out?
For the last six years, this 27-year-old man has been with his 26-year-old fiancée, and they have been best friends since high school.
They met back when they were 13, and have been in each other’s lives ever since. They only started dating right before the pandemic hit, as they went off to college in different directions, though they kept in close contact.
“Our relationship was full of love, laughter, and fun. Anyways, fast forward to 2 years ago, July 2024, I purchased a home for us to live in. We built this home together, and everything is amazing,” he explained.
In August of 2025, she stated that she really wanted to get engaged and then married, so in January of this year, he got down on one knee.
Exactly a week after he proposed, she admitted that she had cheated on him last year with her boss, and it devastated him.
He proceeded to ask his fiancée a slew of questions, and she informed him that the affair took off at the office. It began around November of 2024 and came to a conclusion in March of 2025, but it was pretty hot and cold instead of consistent.
The first hookup happened in July of 2025, and then in August of 2025, his fiancée’s boss was looking to sleep with her, but she promised she shut her boss down because she wanted to get married.
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“She said she never loved him but thought she did at one point. She claimed they only [slept together] 3 times, but I believe more,” he added.
“During this period of time, she was going out to work events weekly, getting super drunk, and coming home late. I told her multiple times I was not okay with it, but she insisted that it was normal when, in fact, it was not.”
He didn’t get mad at her or put up strict boundaries; he went along with her behavior. And then, of course, it comes out that she had an affair with the exact man she said he shouldn’t worry about.
He and his fiancée actually had prior discussions about her boss and how inappropriate he was, as his fiancée always told him about how flirtatious her boss was with her.
Ouch, right? So, he’s not sure how to proceed here, especially since his fiancée says she no longer feels like she’s the same woman. She’s spent the last four months sober and claims to know what she truly wants.
“She tells me that she knows that she wants to marry me and she wants to be with me forever, and although I had all these hopes and dreams of this happening, the fact that she did not tell me until a year later breaks my heart,” he continued.
“I know many people here are probably gonna tell me to break up with her, but can someone please tell me a way that this can work out? I know I was disrespected. I felt disrespected.”
“I know my worth, I know who I am, but this girl feels different to me, and I just really wanted a life with her. I feel angry. I feel sad. I feel betrayed, and she continues to tell me that this will never happen again, and that was an older version of herself. Please help me.”
He should absolutely not marry this girl or start a family with her. The fact that his fiancée tried to make what she did seem better by saying she only slept with her boss three times is insane, and I will bet that the number is far higher than that.
It sounds like her boss was her first choice, and it didn’t end up happening, so he’s just her backup boy. He needs to find some self-respect and leave this liar behind.
What advice do you have for him?
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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
