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Best friend's girl cheated on him with 3 other men


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My best friend "Adam" of 12 years has been with his girlfriend "Jen" for almost 5 years now. I've come to see Jen as another best friend, second only to Adam. He is 23 and she is 22. They've just bought a home together not 4 or so months ago. They seem to have some problems occasionally but overall it appears they get along fine.


About a month ago Jen decided to temporarily break up with Adam. I was the only person Adam told and he relied on me for support through this time. Meanwhile, Jen texted me daily regarding their situation, which made me uncomfortable since I didn't want to be in the middle of it and was somewhat torn between who I should console. I showed Adam every text she sent me as she sent them to show my loyalty toward him and that I wouldn't hide anything from him. The break-up only lasted a week and they've been together since. I really felt like my relationship with Adam became even stronger through the whole thing.


A week ago my cousin was in town to visit me and we went over to Adam and Jen's house one night. Jen was a little drunk and she and my cousin had an all night girl talk in the kitchen while me and Adam watched a movie and knocked back a few beers in the living room. The next morning my cousin told me something Jen admitted to her the night before. Apparently Jen has cheated on Adam with three other men: Her cousin through marriage (he's married to some woman Jen is related to), a friend of Adam's brother, and Adam and I's 38 year old boss.


A long time ago Adam told me he cheated on Jen once with some girl Jen has never met and never will meet. Now I find out Jen has cheated on Adam with three people, who knows how many times. And one of them was his boss of all people, someone he's really good friends with and sees on a daily basis. I haven't had any trouble acting normal around Adam and our boss, but I feel really guilty knowing this information. If Adam found out it would ruin his relationship with Jen as well as his job (where he's been working for 8 years).


I was wondering if anyone would tell me what they'd do in my position. So far I've said and done nothing about it. Personally, if it was me I'd want Adam to tell me if my girlfriend slept with my boss. Adam's like a brother to me. Should I keep my mouth shut and wait for things to work themselves out naturally?

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hmm tricky situation


however, i think you should tell "adam" about it...


"adam" is a grown man, HE can decide what he wants to do about the job and the relationship....but he needs this information to make a informed decision.


u hit the nail on the spot, im sure u would want adam to tell U if 3 ppl close to him backstabbed him like that!

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Say nothing. These things have a tendency to work themselves out all by themselves. I doubt your friends are in for the long, long haul, especially considering Jenn's indescresions. In the end, I think Adam is better off not knowing.


Further, I realize that since you're Adam's best friend you feel like you're letting him down by not telling him. He would probably see it that way. However, it's just not true. Plus, each party could end up resenting you simply for being a whistle blower. You certainly didn't ask for this information.


The ONLY proactive thing I would even consider doing would be to approach Jenn since you're close, tell her that you know what happened, and explain that you're both surprised and disappointed in her behavior. I wouldn't personally take this course of action, but if you feel like you need to do something then I think this would be it. Maybe it would force her hand. Either she fesses up, ends the relationship, or else knocks off her destructive behavior.


In the end though, what's the point of plugging holes in a ship you know is about to sink anyway, especially if you're not even a passenger on said ship?

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Adam is your best friend ... you HAVE to tell him that the girl he is planning to spend his life with is incapable of being faithful. Imagine the day, after they get married, when he discovers she is in another man's bed ... it will happen. Once? Maybe an indiscretion. Three times? An inability to honor her commitment to fidelity because of an itch in her groin.


He did the same once? Well, he's bad too ... but you are HIS best friend, not hers.


Tell him.



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Oh my, I feel for your predicament.


I mostly agree with what Jetts wrote here (not to tell Adam being the upshot), but this does pose a problem:


Further, I realize that since you're Adam's best friend you feel like you're letting him down by not telling him. He would probably see it that way. However, it's just not true.


Later on down the line, when or if (and it will most likely be when, even if it's a long time from now) Adam finds out you had this information but didn't let him in on it, how are you going to explain why? He will see that as a betrayal. "However, it's just not true" is correct, but since he will feel you took her side (i.e., protected her secret), this could really estrange you as friends. I know I'd feel that way if I were him, at least for a long while, even if objectively there were reasons to have kept quiet. So I think you have to prepare EXACTLY what you will tell him if you are confronted about why he was not given this information. So that is something to think about, in advance. You also should prepare for him to come to you one day in a bad state, telling you he just found out about these infidelities, and how are you going to respond? Well-feigned shock? Admission that you knew it? Plan out something that is dignified (and your post suggests you are), true and persuasive.


I think one thing you have on your side, so to speak here, is that you know of Adam's affair. Should he ask you why you never said anything, you could say that you don't feel it was your place to spill the beans about Jen's indiscretions any more than it was your place to spill the beans about HIS. You just want to play fair and impartial, since you consider them both friends, and could not take sides, given both parties were fallible. You will have to make some sense out of this to Adam, but you could "humble" him a bit by referencing his own fallibility and that you honored that as confidential. You simply want to maintain confidentiality accross the board, and that this shouldn't degrade into a question of who you are more loyal to. The explanation is, both parties could get hurt with the truth if the truth were told.


And I, myself, would take the step of telling Jen that you know about this now. Then at least she will know that someone is aware of what has happened, who is close to the situation. This is not to intimidate her, but to give you a chance to air your sense of guilt with the secret. And to make an appeal that she come clean with Adam, to do the right thing. This should be done in a good faith effort to try to help them, but also in a sense this also covers your butt that you DID try to prevail upon her, and admonished her to tell him. That you didn't just passively sit by and wait for the chips to fall as they may. Then when it comes out you knew all along, Adam will see that you tried to do something, short of outing her. Which again, is really not your place.


And will certainly end your friendship with her, which will make your life miserable dealing with them as a couple. You don't want that.

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I agree with tired - but on the other hand simply put he will find out eventually.


When he does you'll be to blame for not telling him.

Further it could also be 20 years down the road and be 20 guys she's cheated on him with - and kids could be involved. By telling him now, HE is making the decision whether to continue the relationship with her. If you don't I'd almost pin the blame for their future predicaments on you. Kinda judgemental but hey, I'd really want to know if I was "adam"



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Adam is your best friend ... you HAVE to tell him that the girl he is planning to spend his life with is incapable of being faithful. Imagine the day, after they get married, when he discovers she is in another man's bed ... it will happen. Once? Maybe an indiscretion. Three times? An inability to honor her commitment to fidelity because of an itch in her groin.


He did the same once? Well, he's bad too ... but you are HIS best friend, not hers.


Tell him.




I would agree with this (I really had to think through my advice NOT to tell Adam), but there is one thing here Zack has brought to my mind that I think is pretty crucial:


How long ago was this activity? At least within the last 8 years, if it was with Adam's boss. If that was the LAST incident, and it was 8 years ago, then perhaps she has already repented silently and has decided to never do it again. This is another reason for you to talk to Jen -- so you can ask her some of these questions. Maybe she will answer honestly, maybe not, but at least you can try to see how contrite and sorry she is. If she has truly regretted it, and is trying to put it past her, then it's up to her to tell her SO when she feels the time is right (if ever) that this happened.


My issue with Adam being told that she cheated by his best friend is that Adam (and Jen) apparently do not know eachother well enough. There is a disconnect here, a lack of judgment (and self-control), in both parties. And each one is not tuned in. Is it someone else's responsibility to open the eyes of someone who is not looking, who is not aware enough? I think life should open people's eyes over the course of time and destiny, it's not another person's responsibility to show them they've made an error in assessing someone's true colors. It's sort of like the teaching a man to fish, not just catching a fish for him. A best friend can be there to be a good sounding board, even try to help indirectly to bring more awareness to his friend, but Adam has to learn to "fish" (i.e., become a better judge of character, and become a better observer of the woman he is going to bed with every night) for himself.


But I do try to put myself in your place, if this were my best, best girlfriend (my sister) and her husband were cheating on her, and I really can't say I'd be able to keep my mouth shut. But that's a little different, maybe -- I am not that close to her husband. It's just a really hard call, because friends should protect friends from danger, but Adam and Jen's destiny is owned by them, not you.

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TOV ... do you really believe she has changed? So even if what she admitted to tbickle's friend was in the far past ... maybe that's just what she admitted to him.


Cheating is a pattern, a character flaw. 3 cheats, even in 8 years, shows that she is incapable of keeping her knickers on when she is attracted to someone.



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Cheating is a pattern, a character flaw. 3 cheats, even in 8 years, shows that she is incapable of keeping her knickers on when she is attracted to someone.


Not to get too technincal, but about the 8 years -- I was just trying to imagine (for the sake of giving her the benefit of all doubt) what the "best case scenario" might be in terms of how long ago this occurred, without recurrance. These people have known eachother over a decade, and that's a long time, so I was thinking it MIGHT be possible these incidents happened close together (say, during a rough patch early on?) and never recurred. UNLIKELY, I admit, but if we were to give her the benefit of the doubt (because anything is possible here), saying this was a long time ago, how long ago might it have been? tbickle76 said one of the incidents was with their (his and Adam's) boss, who Adam has worked with for 8 years. So it could be possible that she cheated twice over a decade ago, and once around 8 years ago.


Not that she has cheated 3 times in 8 years. That would be just atrocious!


Not that it isn't really bad, and I agree with you, Zack: this does seem to be a pattern, a serial cheater. It's just such a weighty charge, and the stakes so high after what, 12 years together (and Adam not being an angel either), I am trying to presume innocent before guilty, since we really do not know for sure when these incidents happened along the timeline. If the last one was 8 or so years ago and their relationship has gotten more and more serious, and she has done nothing since, what then? How can we/you know her mind just from this post?


Maybe I will be called naive (I personally, to my knowledge, have not been cheated on, and have not cheated myself, even though I've gotten close a few times to danger), but I'm just trying to look at all possibilities. One being that the fling with the boss didn't happen last week or last year or even 5 years ago, but farther back and she regretted it.


Regardless, though -- it stinks what she's done, she is someone untrustworthy at this point, and how the timeline materially affects what the OP should do is questionable, I agree. I am inclined to think that if he is with a woman who has cheated right under his nose a few times, something is wrong with his astuteness and being clued in to this relationship and woman. I am not saying I am imperverious to being cheated on, but something is amiss if serial cheating is going on and the a person misses all the signs and has no clue. Don't you think? Something more fundamental is awry about his power of intuition/observation and their dynamic -- the communication, the intimacy, just knowing eachother. That is beyond the scope of what the OP can affect, I think.

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I think jettison has some great advice.... people have a tendency of 'shooting the messenger.' you weren't there, you didn't see the cheating with your own two eyes, and your information is second-hand information. both of them may accuse you of "lying" due to your own selfish motives.


However............. there is the STD question. If she has been unfaithful to him, I believe he has a right to know, so he can get an std test. many stds can go undiscovered for years. This issue for me trumps the "stay ou of the middle" argument. I would want to know if my partner cheated on me, so I can get an STD test done.

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I am in the you need to tell him camp - but only if you are VERY sure of the information (and I mean very sure). Yes, there is a risk he WILL "shoot the messenger" but honestly in your shoes, that would be something I would HAVE to risk in order to be their friend and maintain the honesty and other values I find important to that relationship. Even if the friendship was over, I would know I did the right thing - and I think eventually they may see that too (whereas if they found out later and knew you had been hiding it....hmm...think that would be worse).


I hesitate to say their relationship is not as "perfect" as you figure if they have both cheated; and I would say his indiscretion is just as bad as hers, but I would say that as HIS friend, you really need to tell him (despite his own indiscretions) about this information as he is your "best friend" after all.


As painful as the information would be to hear, I know in that situation I would prefer my trusted friend to tell me due to the emotional risk and health risk I am put at by cheating.


It's fine and dandy to say "he needs to be a better judge of character" (and if you were not close I would say stay out of it) however if he has been with her for so many years from quite a young age (probably the only real "long term" relationship he has ever had) he also has little context or experience to base that on - when you are with someone at such a young age for so long, sometimes issues like being able to be independent in order to view things in that manner are lost. Furthermore, even if you are a good judge of character....some people are just really, really good at hiding it. More so those whom don't feel much remorse for it or guilt if they are able to live their lives as "normal" despite the indiscretions.

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Thank you all so much for your responses. There's been a lot of suggestions and I'm going to have to consider all your points and think about it for a while before I even decide what to do.


But it seems I confused people a little with all these numbers. Me and Adam have been friends for 12 years. He has only known Jen for 5 years, and his boss for 8. Also theres more information my cousin told me that I left out because I didn't think it was important, but it's been brought up: Jen slept with Adam's boss about 3 months ago. She slept with her cousin in law about 4 months ago. I'm not sure about the third person.


Jen was saving herself for the right guy, so Adam was her first sexual partner. To Adam's knowledge he has been the only person she's ever been with, so he feels like he doesn't have to worry about STDs.


As for Jen feeling guilty about what she did, from what she told my cousin that's not the case. She told my cousin how great the sex was with Adam's boss and that she was bored with her sex life with Adam. She also told my cousin how she's too scarred to tell Adam or anyone about things that are bothering her because she feels nobody would care. And why she opened up so much to my cousin I'll never know, she doesn't really know her that well and as never really talked to her much in the past.


Thank you again for the suggestions. I'm leaning towards confronting Jen about it but I'm still not sure at all.

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you sound like a really good, concerned friend. and thinking things over is a really good idea.


everything else aside.... cheating on your bf is bad enough...... but to screw your COUSIN'S husband??? that is really messed up. i mean, that is family. that's really low. jen does not sound like a good person at all. ok, fine, sex with her bf is boring, but sleeping with your cousin's hubby is just really really really low. i hope adam doesn't marry her.

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Do you mind if I ask how old Adam and Jen are?


Jen sounds like a very immature and lost girl who has no moral compass whatsoever. And I am wondering if they are planning on marrying at too young of an age. Neither of them has much experience, let alone ability to make sound decisions about who and what they are getting themselves into. It's also very odd that you say Jen "saved herself" for the right guy...but then has such a casual attitude about sleeping with people and cheating, and keeping the lie going, and claiming to be afraid of telling anyone (especially her intended husband!) about her concerns (such as a boring sex life.)


Something smells fishy to me here, and I'm not sure what. Some things are not adding up. I am wondering if she might actually be lying about something here, and if so, what. I mean, why would a girl who "saves herself" (which means she is not promiscuous by nature, and has a more idealistic view of sexuality) suddenly become the town wench, without even a conscience? And why would she unload this to someone she barely speaks to, saying no one else would care? And why is she planning on marrying a man who she feels "wouldn't care" about something so important as her feeling that their sex life is missing something? Parts of this character sound like a somewhat timid girl who has little going for her in the way of communication skills, who has fostered some "wholesome" attitudes about monogamy and sex, and on the other hand, she sounds like an incredibly unconscienable, selfish and disloyal woman who can't even keep her own self-described secrets to herself. The picture doesn't add up for me.


Are you sure she hasn't lied to your cousin in her story to get some kind of attention? As a cry for help? It's just very strange to think that a woman who has waited for Prince Charming to deflower her, because he is "the right one" will then sleep with your own family and then her Prince's boss the following month, when they are making marriage plans.


And if she really feels that she can't sit and talk to her intended husband about her thoughts, troubles and unmet needs, she (and he!) are in no position to be getting married. Simply put, it sounds like their level of communication is stunted at best, nonexistent at most.


Since this is a very odd picture, and you don't have all the facts correct, I would really consider talking to Jen alone, and try to figure out what on earth is going through her mind. She sounds very lost, frankly -- lost somewhere between pathetically innocent, or ethically depraved. You seem like a level-headed guy, someone who thinks things through well, and I admire you for that. You might be the only solid rock in this situation. If you bring it up to her, it would be a very good way to impress upon her the danger she might be putting Adam in, with the STDs, and the very, very bad idea of going into a marriage where you cannot discuss your needs without resorting to the kinds of things she's done. If she has done them.


Good luck in this, my friend.

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In his first post he said he is 23 and she is 22, so they have been together since 18 and 17ish! All I can say is that someone can change a lot between 17 and 22 and while she may have had thoughts of "saving herself" at that age, her views can have changed a lot since then particularly when she realized that someone else can't save her from herself if that was what she was hoping for.


I don't deny though that there is something very amiss with the whole situation.

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IMO, Jen wants to be found out and use this to leave Adam, whether she really cheated or not. As to whether I would tell Adam, I'd go to Jen first and confront her with it, then if I thought she really did cheat, I'd insist she tell Adam herself and confirm with him once she had.


Do it fast and clean and speak of it no more once you've done it.

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i also agree, you should go to jen first. tell her what you heard and that you feel that you are in a position in which you have to tell adam about it but that you would prefer for her to do so and that in the end it would be better for her and adam if she was the one to figure out how and when. give her a timeline (say two weeks) to tell him. stay hard and fast and don't let her try to talk you out of it, cause more than likely she will.......

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Sounds like a really messy situation but there is one point I'm not sure if anyone else brought up here.


Adam also cheated on Jen.


I'm always one for honesty, but please be sure of your facts here before you tell Adam anything because he may not thank you for letting him know. After all, she's only supposedly done what he did. And before anyone says ah but it was 3 times to his once..........cheating is cheating however you look at it.

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not a nice situation to be in. but i would tell my friend for sure as i would want to know if my BF had cheated on my 3 times with the last time being 3 months ago. if i found out my friend knew and didnt tell me i would be VEXED... and as someone else mentiond... std's... yuo dont know if she used protection or not so yuo friends sexual health is at risk.

to me it seems like she was savign herself as she didnt know any different .. but now she's ha a taste for sex she wants to go and see what its like with other ppl... and im near enough sure that it wont be the last time either if it was only 3 months ago.


you should tell him 100%.... id rather lose a friend coz i was truthfull to him (coz theres a chance that he will be back once he realises whats she is like) then lose a friend coz i kept something hidden from him.. wouldnt yuo??


let us know the outcome

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  • 2 weeks later...
i will format this in bullet points


.you were best friends with adam before this girl came along.

.you wont be best friends for much longer if he finds out you are hiding this from him

.he DESERVES to know that he is wasting his life with this girl

.tell him


Okay people, don't judge me too harshly for this, but I say tell him. I've been there and done this same sitch where my current best friend had to confront my former best bud, who is a serial cheater. This is the truth, remember folks, were not talking about marrieds with kids here, we're talking about bf/gf who are starting to get serious and he needs to know. STD's are very serious and we do know some can kill. This is NOT something to trifle with!!!

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