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Her Boyfriend Asked For Permission To Sleep With An Older Married Woman He’s Hooked Up With Before, And He’s Pushing For An Open Relationship

profile Bre Avery Zacharski | Jul 22, 2026
Jul 22, 2026
Pretty girl walking on the street from
Serhiy Hipskyy - stock.adobe.com - illustrative purposes only, not the actual person

If you were in a committed relationship with someone who asked for permission to sleep with a friend with benefits from their past, would you let them do that?

This 35-year-old woman has a 32-year-old boyfriend, and his very first relationship was open. His second was not, even though that’s what he wanted. Then he started dating her, and he’s had a hard time wanting to stick to monogamy.

“He gave up on asking for an open relationship when I began packing my things from his place. He held me and didn’t want me to go and said he didn’t need it,” she explained.

Her boyfriend is still constantly bringing up having an open relationship. One time they did have a thing with a random girl because she was curious.

Following that incident, her boyfriend insisted he is picking fights with her because he has such a great need to sleep with women other than her.

Over the last decade, her boyfriend has hooked up with a married woman in her fifties, and her husband apparently knows she likes to get around.

This woman will book hotels close to her boyfriend to have some fun with him, and he used to say this woman was the best he ever had…but lately, he’s claimed it’s her.

“He wants permission to sleep with her again. We became a couple in December, and he has been loyal since. The first time it almost happened with her was last month in June, but he agreed to the day I was coming back from a work trip to the airport and would need a pickup,” she added.

“He felt bad, so he canceled, but he begged her to make it work, and she said she wouldn’t be able to until July. Now she’s saying she can come this weekend and next, but he and I are leaving for his family’s vacation this Saturday and coming back next Saturday.”

Pretty girl walking on the street from work
Serhiy Hipskyy – stock.adobe.com – illustrative purposes only, not the actual person

“He told me he didn’t reply to her, but I saw where he texted asking if she could meet up during the week instead of the two days I would be out of town on a work trip. She couldn’t. So now I have to decide if he can sleep with her this Friday night, and if so, I would stay at my place even though [my little dog and I] have slept every single night at his place for months. He asked if he could come see me after, and if he showered, would I want to [sleep with him]?”

They honestly are just having so many problems regarding her boyfriend’s desire to see other women, and not just her. Several months after he committed to her, he confessed while at a club with her friend that he missed the single life.

From there, he said he was in love with her, but a week later, he took it back while insisting on an open relationship. He even talked about a girl younger than her that he said was better at romance than she is.

But then her boyfriend confessed that he only said that to push her away. He switched up again, pushed for an open relationship, and said he wanted to see this younger girl as well as the woman in her 50s he’s been hooking up with for 10 years.

She’s really not sure what to believe anymore. She is in love with her boyfriend, and he has stated he is getting close to feeling the same way.

She thinks a physical romance is special and sacred, but since her boyfriend doesn’t view this the same way, and if she allows him to seek out other women, she’s not sure how he will ever fall in love with her.

“I can’t imagine life without him. He’s my best friend. Other than this issue, he makes me so happy. I wish he could give up the need for…variety,” she continued.

“I think the fact that his first girlfriend gave in to an open relationship and this older married woman has slept with him for ten years, and then the fact that he says he feels so handsome, like a movie star, means he thinks he can get away with this.”

“Maybe if I truly love him, I should let him go to find [another] woman? But the thing is, he doesn’t even really want me to sleep around. He says he would allow it if I wanted that (but I don’t), but that he doesn’t prefer it. He also says he’s not jealous or possessive. How do I navigate this?”

I just don’t see how this relationship is going to work, because they both want very different things. One person in a relationship can’t be monogamous while the other isn’t.

And her boyfriend already admitted he was going to cheat on her, except she needed a ride home from the airport. Gross. Just because you’re in love with someone doesn’t make them the right fit for you, and that’s her reality.

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