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'My best friend sleeps with married women and he crossed the line last week.' UPDATED 2X

'My best friend sleeps with married women and he crossed the line last week.' UPDATED 2X


A friend's toxic behavior can be written off as entertaining until it affects you personally.

"My (25M) best friend (25M) sleeps with married women and he crossed the line last week."

My best friend has a thing for married older women.

Over the years he has had surprising success in this area.

It started when he was 18 and slept with a married 30 year old woman with a kid. They were both waiters at a restaurant and after months of flirting she slept with him. In the 7 years since there have been 12 of them. All married or engaged, with ages ranging from 30 to 52. In the beginning I thought the whole thing was funny but as the years have gone on I have grown disgusted by this behavior.

If we are at a bar and he sees a bachelorette party he is hitting on the bride to be. He coaches his nephews little league team just to meet the moms. He’s had to leave 3 different jobs because he was sleeping with married coworkers and the husbands found out leading to confrontations while he was on the job.

The last straw for me was last week. I recently got engaged and my fiancé’s family threw us an engagement party. It wasn’t a surprise so my fiancé and I both invited who we wanted and one of the people I wanted there was one of my former managers at work, let’s call him Tom.

I am a CPA at a big firm and Tom was really a mentor to me when I started. He left to work in industry but we kept in touch and are still close. Tom is 40 and just the nicest guy you will ever meet. So he and his wife (38F) come to our engagement party.

I had never met his wife before, she is beautiful by the way. And at one point during the party I see my friend talking to Tom’s wife while Tom took a phone call. I immediately go over and interrupt the conversation and pull my friend aside and tell him to not even think about it. My friend says he wasn’t. Which was bulls#$t but I thought he took my warning seriously.

I was wrong. A few weeks later Tom calls me and tells me that his wife had been acting strange since the engagement party and he went through her phone and found text messages with another guy. The texts included nudes exchanged on both sides and it was very clear that they had met up for s#x. Tom had confronted his wife the night before and of course it was my friend who she’d slept with.

Tom was devastated, crying on the phone. He wasn’t even angry he just wanted to know why she did it and was asking me to talk to my friend to get some more details. I called my friend right after I got off the phone with Tom and exploded on him, basically ending our 20 year friendship.

It’s been a week and my friend hasn’t stopped apologizing. Other than his despicable behavior with married women he has been a good friend to me. We have been like brothers since kindergarten. It hurts to throw away someone who has been such a big part of your life but I just can’t be party to this anymore. I’m making the right decision, right?

TL;DR: My best friend sleeps with married women and I don’t know if I can be friends with him anymore.

Not long after posting, OP shared an update.

EDIT: I do want to add that aside from my friend’s bad morals with married women, he has been a really good friend to me over the years. If I needed anything he was the first one there. He’s never slept with any of the girls I’ve dated and never tried. A lot of people are also saying that my fiancé would be next but that is ignoring the fact that my fiancé would never cheat on me.

A cheater has a personality defect. My friend clearly has one but so do the women that cheat on their husbands. They are all inherently narcissistic and care only about their personal gratification. My friend hit on my fiancé before we met and she shot him down abruptly then. I’m not worried about her. But I am sick over Tom and I do bear responsibility for what happened.

People shared their thoughts on the matter.

druscarlet wrote:

Yes. He did not respect your request. He lied to your face and will do it again. Ruining other people’s marriage for sport is sad. I would not put hitting on your fiancé past this sick guy.

OP responded:

He actually hit on my fiancé first the night we met and she shot him down. My friend usually isn’t shot down so I felt I needed to go and talk to this girl and now we are getting married. He wouldn’t cross that line with me I don’t think but who knows if she was into him.

Beginning-Stop7646 wrote:

Although your friend is a selfish AH and needs therapy it takes two to tango. Every single one of those women should've and could've have said no, but they didn't. For whatever reason, they chose to cheat on their spouses.

I am pissed for you though bc you asked him personally not to do it again especially towards someone you looked up to he still did it. He's not trustworthy whatsoever. What if he tries again with your wife or someone else's wife in your family?

OP responded:

I justified his behavior when I was younger because he wasn’t the one married. I thought what the hell is wrong with these women that they would throw their lives away for s#x. But deliberately trying to tempt these women started to disgust me a few years ago

Disastrous-Assist-90 wrote:

You need to be honest with the fact that you were totally fine with him destroying other peoples lives right in front of you, but because it didn’t directly impact you, you excused it.

OP responded:

But I wasn’t fine with it I just wasn’t ready to end a 20 year friendship over his poor decisions.

Eatyourfriendz wrote:

He’s done it for years and you let it slide because it’s never been close to anyone you’ve been involved with. Now it hits close to home and it’s a bit too uncomfortable? I’d definitely wonder about the odds of him trying to do this to you as well.

Regardless of him being previously rejected. The dude has an issue that’s deep seated and he needs therapy for, so it isn’t that far a stretch to see it take a turn and take a swipe at yours.

heavy-hands wrote:

Your friend is a disgusting pig with what sounds like either a blatant s#x addiction and/or just a general disregard for the feelings of others. He’s lost THREE jobs???? And he doesn’t see the problem????? This is so foul I don’t even know what to say. I could never be around someone like this.

ETA: if I were your fiancé I’d be seriously second guessing this entire relationship. You are the company you keep and your morals sound compromised at best. Your friend is pathological and you’re definitely an enabler.

A week later, OP shared another update.

It’s been about a week since I posted and I wanted to give an update on how things ended up with my now former friend. I agreed to meet with him last night and hear him out. So we went for a drink and he apologized profusely for putting me in this spot and said he would never do that again.

So I took this opportunity to really express how disgusted I was with his behavior and that I couldn’t be friends with someone that intentionally tries to ruin families. I tell him Tom and his wife have 2 children they were happily married and he’s now destroyed their family.

I ask if that is something he feels bad about. He says yes but I can tell he’s bullsh#$ting. I ignore the fact that he’s lying because I want to know how all of this went down. Tom’s wife didn’t want to share alot of detail with him so I promised that I would find out as much as I could.

So I ask to see the texts between them. He resists but I threaten to walk out and never talk to him again so he gives me the phone. He contacted her on Facebook after the party and they talked there for a day or two before switching to text. The conversations turned s#x*al very quickly and it was clear that Tom’s wife was interested in a quick fling.

She says in the texts that she loves her husband but that doesn’t stop her. I’m shocked by this but my friend isn’t. This isn’t the first happily married woman who took up is offer for strings free s#x. Beyond what is in the texts my friend says Tom’s wife just wanted a temporary escape, to be someone she can’t be with her husband and once she got it out of her system she would just go back to normal.

Then he starts telling me what she was like when they were together but I stop him. I say we aren’t teenagers anymore and none of this is funny. I tell him I’m done with this and both you and Tom’s wife disgust me. I leave and block his number. I know I should have done this years ago but I didn’t. I call Tom after I leave and lie. I say I wasn’t able to get any detail. I can’t tell him that his wife just wanted some wild s#x.

That isn’t something I would want to know. Tom and his wife are a going to go to counseling. If it were me I’d divorce her. The level of disrespect is off the charts but maybe Tom is a better man than me. My fiancé is happy that I have finally cut off my now former best friend. But I am sad, I hope he gets help someday before he f#$ks with the wrong guys wife. Thanks for listening.

The comments kept coming.

AllInkalicious wrote:

You are making a massive mistake in not telling Tom and it makes me doubt your sincerity.If you know that’s she purposefully betrayed him for meaningless s#x why would you not tell him?

Who knows what’s she said or promised that can be contradicted or shown to be more lies with your truth. After years of applauding and supporting your scumbag friend’s behaviour, this is your one chance to help someone.

OP responded:

He already knows they had s#x and he’s seen a lot of the texts. I just couldn’t tell him that she wants to have wild s#x with someone else that she doesn’t want to have with him. She apparently just isn’t attracted to him like that, he doesn’t bring that out in her. I wouldn’t want to know that. I don’t know how I would have s#x with her ever again know she thought they of me.

tattoovamp wrote:

YTA for staying friends with this AH.

Individual-Foxlike wrote:

It was funny when it didn't affect you, huh? He has a history of enjoying stomping on social norms. Of course he ignored your request. He hasn't been a respectful person since the beginning, and the only difference this time is you got caught in the fallout.

WxaithBrynger wrote:

Honestly, you're a f#$king idiot. You're cool with him participating in disrespecting other people's marriages and relationships but you draw the line at your own. You're worse than he is because you're condoning the shit he does.

You two deserve each other, and your fiance deserves someone that has a moral backbone to stand on. You didn't give a s#$t about what your friend was doing till he crossed YOUR boundary. F#$k all the way off.

Sources: Reddit
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