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Bisexual Woman Refuses To Give Boyfriend ‘Free Pass’ After She Sleeps With His Female Friend

Man and woman arguing in the bedroom
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As much as two people might love each other, sometimes relationships get a little predictable and for that reason, boring.

But when a couple tries to “spice things up” without totally making sure that both people are comfortable with the changes, the relationship could be over before it could even really shift, cringed the “Am I the A**hole?” (AITAH) subReddit.

Redditor teethtreeboil was in a happy relationship with her boyfriend when they decided to try out a threesome to change up their dynamics a bit.

But when the two started disagreeing about the details of the threesome arrangement, the Original Poster (OP) realized the changes might have ruined what they had.

She asked the sub:

“AITAH for not giving my boyfriend a free pass after I slept with his friend?”

The OP and her boyfriend recently took their relationship in a new direction.

“My boyfriend, Ryan (25 Male), and I (24 Female) have been dating for a bit under two years. Recently, we’ve been getting more experimental in the bedroom.”

“I pitched the idea of a threesome with another woman (I’m bi) and he suggested his friend Jessi (25 Female), who is also bi.”

“I had met Jessi quite a few times as she is very good friends with Ryan and they’ve known each other for a long time.”

“He was upfront with me when we met that they dated for a few weeks like seven years ago before amicably splitting due to lifestyle differences (Jessi is a party girl, anti-religious, child-free, Ryan said there were too many differences between them, and they haven’t messed around since but stayed friends).”

“Jessi and I have hung out a few times, just the two of us, and I consider her my friend now too.”

Everything was going well for the three of them.

“One day when she was over Ryan pitched the idea to Jessi. Jessi seemed a bit shocked but agreed.”

“We got down to business and… it was nice. I thought we all had fun. We’ve done it a few times and I thought everyone was on the same page and it’s not weird.”

“Well, now it is. The other day Jessie stayed over and slept in our bed with us. Ryan went to work early and it was just Jessie and I.”

“I woke up to her trying to initiate sex with me (politely). While I was interested, I declined, saying Ryan wasn’t here, and he wouldn’t be ok with just us messing around.”

“She then showed me she had texted Ryan earlier specifically asking permission to sleep with me without him. He responded, ‘That’s fine, as long as I get a free pass, too.'”

“I thought for a second and came to the conclusion that the idea of him and Jessi together didn’t upset me, as I trusted both of them. So I was okay with him sleeping with her as long as he told me about it.”

But then the relationship got unbelievably complicated.

“We really should have talked about the details more because this is where it all went wrong.”

“Jessi and I did sleep together without Ryan, it was fine and all, but when he got home later, Jessi asked him when he wanted his free pass.”

“He said, ‘Not sure yet, gotta try to talk to this girl at work I want to use it on.’ Both Jessi and I were confused as we thought he meant a free pass with JESSI but apparently he meant a free pass with ANYONE.”

“Which I was not okay with. I knew and trusted Jessi, which is why I agreed to it.”

“I told him this and he said it wasn’t fair that I could sleep with whoever but he couldn’t.”

“I told him it’s not WHOEVER, it’s this one person we both trust.”

“Jessi then left us to resolve the argument. Ryan said the threesomes with Jessi are mostly for me, as he isn’t all that attracted to her. So he wants someone different.”

“I kind of feel like I got trapped so I told him no.”

“Now he’s not speaking to me and I can’t tell if I’m the AH. I mean, I did sleep with his friend.”


Fellow Redditors weighed in:

  • NTA: Not the A**hole
  • YTA: You’re the A**hole
  • ESH: Everybody Sucks Here
  • NAH: No A**holes Here

Some cringed, believing the relationship ended as soon as it was opened up.

“I’ve never known anyone with an ‘open’ relationship that worked out. If you just want a friend-with-benefits relationship, then it’s fine, but a relationship with a stable future isn’t going anywhere when you’re being intimate with other people. Best of luck to you.” – Huge-Lawfulness9264

“Open relationships are generally more successful when they start that way and the people involved are familiar with the dynamic. People without any open experience switching from a mono relationship very often ends up being messy especially with it’s only one partner that really wanted it.” – pup_101

“This sounds all convoluted and complicated.” – Pandorasconservation

“It’s not doomed because of a threesome or the idea of opening a relationship like others have said though. It’s simply doomed because of a massive difference in expectations that arose from said interactions.”

“If two partners can not agree on the terms of their relationship, no matter what type of relationship it is, then the relationship is inevitably doomed.” – Latsirroff

Though the OP suggested the threesome, others were concerned by the boyfriend’s motives.

“Listen, if he already has someone picked out, it didn’t matter what you agreed to, he’s going to sleep with her, and was planning to before this ever happened.”

“It’s over. Move on.” – better_as_a_memory

“NTA. Your title made it sound like you cheated.”

“In the context asked, why wouldn’t you have thought that he meant the friend? Why didn’t he already assume the friend was the one the pass was for.”

“He’s looking for permission to cheat. Tell him the pass is for Jessi, that’s it. If he has a problem with that he knows where the door is.” – No-Personality5421

“This is exactly what he wanted by saying he’d get a pass, too. He knew beforehand he wanted to sleep with someone else besides OP and Jessi. He has been waiting for the opportunity.”

“He’ll most likely attempt to cheat, given his desire to sleep with her and his upset over believing he’s being denied his pass. He knew what he was doing with his ask.” – trvllvr

“NTA. This man wants his cake, ice cream, cookies, and to eat it all in front of you. Leave, and take Jessi with you!” – bhardy10

“He knew what he was doing and what you girls thought it meant. Clearly when he came is was even more evident.”

“You are not the a-hole here. You had something steady with someone you both agreed to, and he’s changing the agreement. Yeah, this may be something you break up over because he’s clearly moving to a standard open relationship. Unless you want that. But this game he just played is a huge a** red flag! For sure!” – stinkytheferret

“This boils down to boundaries. It sounds like you two had already cleared the threesome hurdle but never the open marriage hurdle. He’s now broached the subject and you will need to have another conversation.”

“To be honest, I’ve never seen a relationship go this direction and survive, and I’ve been Jessi.” – NotSoNice_Needlework

One Redditor tried to offer a helpful solution to the OP before calling the relationship quits.

“Origin story of the situation aside, what this boils down to is that he wants something, that you don’t feel comfortable with. Discussing that, seeing and understanding each other’s position (even without feeling the same) will be key.”

“Once you’re there, as a couple you go with the most ‘conservative’ opinion that exists between you. You should both understand that your relationship is what matters here, not any of the extra ‘bells and whistles.'”

“The tricky thing is to not make it transactional. He’s not getting his free pass BECAUSE you did this other thing, he might get it because you both want him to have a nice experience. And likewise, he’s not NOT getting it for some previous event, it’s because it’s not right for both of you as a couple.”

“This setup also allows for changes over time. Something that might normally be fine, might not be right now. It’s okay to not always feel the same. Your comfort, either with the situation or person, can change and there should be space for that. Likewise for him.”

“It can be tough, but if you nail it, there’s so much healthy conversation and connection to be triggered by having these discussions. I’ve been on both sides, not ‘getting’ a treat I feel comfortable with but my wife doesn’t, and putting the brakes on a situation myself.”

“At the moment it sucks, either you’re not getting what you hoped for or you feel like the party pooper, but in the long run, it enables some amazing things! Hope you guys work it out!” – FriendlyDavez

The subReddit found this situation to be an absolute mess, and while the OP was the one who suggested the threesome in the first place, they could also understand where her misunderstanding and discomfort around the “free pass” were coming from.

It was clear the dynamics of the relationship were changing, and unless both of the original people in the relationship were comfortable with the situation and willing to communicate, it might be time to move on.

Written by McKenzie Lynn Tozan

McKenzie Lynn Tozan has been a part of the George Takei family since 2019 when she wrote some of her favorite early pieces: Sesame Street introducing its first character who lived in foster care and Bruce Willis delivering a not-so-Die-Hard opening pitch at a Phillies game. She's gone on to write nearly 3,000 viral and trending stories for George Takei, Comic Sands, Percolately, and ÜberFacts. With an unstoppable love for the written word, she's also an avid reader, poet, and indie novelist.