It's only true that his cheating is between him and his wife, if you're not being asked to cover for him. But since you, and presumably others at work, are covering for him, it is in fact your business now too. If you are helping with the cover up, you are an accomplice to the crime, so to speak. You are in this up to your eyeballs. You are directly involved in his affairs.

Worse, it sounds like this has the potential to damage the business. If the affair(s) come to light, his wife probably owns half his interest in the business, and could demand payout in a divorce (depending on what state they live in).

Fuck that.

If I had a brother (or friend or whatever) who was cheating on a partner, and I wasn't involved in it in any way, I would say it is not my problem. It is between the two of them, and none of my business. But the minute my brother (or friend or whatever) started asking me to help cover up the affair, I would walk away from the whole thing. I would flatly have nothing to do with covering his tracks.

Your previous instinct to get out of the business was correct. Your return to the business (and the coverups) was a mistake. Get out.
Before you do anything, consult with an employment attorney. For all you know, you may have a claim to a share of the business.
As soon as the divorce is final, marry his wife. Adopt his children. Live like a warrior.

Really, you should distance yourself- like lots of distance. Having been in a family business for several decades, there is not enough distance (and, I took several physics courses at a good school) to protect yourself from heartbreak.
God, the poor wife. Can you imagine knowing something was off and having everyone just repeatedly bald-face lie to you.
@3: It's not at all clear from the letter, and Dan doesn't say, but I thought LW was female.
The lw is a woman.
Never lie for someone to help them do something shitty. They don't deserve it. But I realize there are practical matters... what @1 and @2 said. Please don't feel bad about the position HE PUT YOU IN.
It is kind of an eerie parallel to the time not very long ago when people said closeted gays couldn't be trusted because they were such practiced liars, and vulnerable to blackmail. Once you take away the reason to lie all the collateral damage from lying evaporates.
he's doing so without care or fear of repercussion

Would that we could all be so bold as to pursue our lives without such fears.
@5, @6

Same-sex marriage is legal now.
Wait — he said she’d no longer be asked to cover for him. So why is she covering for him?
@8 - When she came back to the business and fell right back into the same situation and started lying again, I think at that point you have to say that the LW put themselves in the situation. As the great George W once said: "Fool me once, shame on you. Fool me twice ... uh ... fool me and you can' fool me again!"

@13 - Exactly. This is affecting how she's men because of how easily "they" can lie and at the same time she's also constantly lying to her brother' wife also.

LW - The fact that she "corners you" about what he's up to means that on some level she knows, and you and your brother are kind of gaslighting the poor woman. He's being reckless and a complete dick etc. but maybe you should take a minute to look at what you're doing and just decide if you want to be an honest person or not. If you do, stop lying to his wife, and if she asks you something you don't want to answer, just be honest and tell her that she needs to talk to your brother about it. I'm sorry your brother is going through this and dragging his family along.
@14 (me) I need to proof read before I post. I feel like I owe anyone who read that an apology
LW: You could resolve the situation--in which you demanded that you not have to cover for him--by just not covering for him.

If he freaks out, remind him that you had a deal.
I agree with @2, safeguard or withdraw whatever stake you have in this company as it's only a matter of time before it implodes due to a sexual harassment suit. After that what I would say to any inquiries is, "If you know my brother, you know (or at least suspect) why I'm leaving. If you don't know him, it's none of your business." What you are doing is being the enabler – allowing his self-destructive actions to flourish via your passive participation. Run, don't walk, out the company door, and tell him why. He had his second chance, don't give him a third. As for the wife, when cornered, how about, "This is your relationship, not mine. You have to work it out on your own, but I'll offer whatever support I can if you need it."

As for "this whole ordeal has left a bad taste in my mouth with regards to long term commitments", don't let the assholes of the world get you down. They're the minority even if they do get the most press.
Oh, and as for, "how easily a man can lie and expect others to lie and cover for him", I've seen plenty of women who can more than hold their own on the deceit scale. Assholery is an equal-opportunity employer.
I'd say that HELP's brother is also possibly a misogynist, at the least someone who doesn't respect women, especially younger ones. He's treated the co-founder of his business very shabbily, as if she were nothing more than a lower echelon minion whose only role is to cover-cover-cover for her boss. I doubt he would have behaved the same were his investor-sibling an older brother.

I agree with the others above counseling HELP to get her stake out and then to inform the BoD.
There are many valid reasons that LW has to find this situation distasteful, however, LW also makes some dubious claims, such as suggest that this issue is effecting her livelihood, which seems unlikely given the known facts, or suggesting that her brother's behavior is "legally foolish," which is far fetched unless their is something criminal occurring that is unstated. I wonder then whether she is grasping at artificial reasons to justify a candid conversation with her sister-in-law.

Additionally, LW also introduces the fact that her brother's behavior has colored her view of men, which Dan doesn't bother to address, but seems to require some acknowledgment with respect to her discomfort.

LW also mentions in passing that her parents are aware of this situation, but doesn't mention what, if anything, they've discussed. I think parents are justified in speaking a child that is making significant mistakes in their life, shouldn't LW discuss with them about speaking with their son?
@20: "Additionally, LW also introduces the fact that her brother's behavior has colored her view of men, which Dan doesn't bother to address, but seems to require some acknowledgment with respect to her discomfort."

If you saw a black person commit a crime, and then started viewing all black people as criminals, how much acknowledgement or respect should we give your newfound racism? It seems like politely ignoring that part is the nicest possible response.
Dunno @20, I don't think "politely ignoring" racism is the answer at all.
That it's affecting her livelihood is NOT a dubious claim. Read that part again:
it's affecting my livelihood. I've decided to leave my comfortable position here because again I don't want any part in this.
Depending on her skills and level, leaving a job TWICE may look suspicious to a new employer; even if she has reason to leave this job - again - because she's lost all respect for her brother and doesn't want to be beholden to him for her paycheck, she's going to have to come up with a reason that doesn't dissuade a new employer from hiring her.
Sorry... should be @21
"This is not only juvenile behavior"

Her behavior is juvenile. Expecting someone to act otherwise than the way they have shown you they will act; tying her livelihood to someone she doesn't find trustworthy, and, yes, Eudaemonic, seeing all men as cheaters because she now knows her brother cheats. She needs to grow up and establish proper boundaries between herself and her family of origin.

SublimeAfterglow @20, running to their parents in this case isn't going to help her establish those boundaries.
@21: The LW does say "I've developed a lack of trust in those closest to me" and "this whole ordeal has left a bad taste in my mouth with regards to long term commitment." Perhaps, if the LW is hetero, "the way I look at men" is a hetero-centric stand-in for "the way I look at intimate relationships," since for a hetero woman those relationships would be with men.* It might be worthwhile, then, to address the issue she developed with intimacy and trust.

*After a bad relationship, I've noticed many women speak ill of "men," and vice versa, when the real issue is their own vulnerability to manipulation. Instead of admitting they have a problem being easily manipulated, they tend to project blame onto the group from which the manipulator came--in intimate hetero relationships, the opposite sex. The LW seems to be vulnerable in this way, since she returned to the business when she should have stayed away, and she lies to cover for the brother.
Many years back, one of my roommates was cheating on his girlfriend. When she asked me if Roomie was watching TV with my on DATE, I'd just play dumb and say "I don't think so." Once Roomie realized I wouldn't lie to cover for him, he just roped someone else in as an alibi.

Moral of the story: covering for someone is enabling behavior. If you put a stop to those requests right away, you can usually stay clear of the drama.
Well wasn't she silly to think a leopard changes his spots. @1 got it re legal mess ahead. Do what you need to do to protect any legal interests in the business, and step right away from any involvement in his lies.
HELP "was coaxed to come back and work for him under the condition that I would no longer be asked to cover his tracks, etc. This was fine for awhile until *it* started happening again and again and again".

I know this is serious, but I can't help but giggle. What exactly started happening in the passive voice? That Brother was asking-- passively as though he had no agency? Or that HELP covered for him, again like s/he* similarly had no agency, it was something that s/he just started doing the way people have no choice but to bleed when cut.

*(For the first 2 paragraphs, I pictured HELP as a younger brother. For the last 2, I pictured a younger sister. What sort of bad feminist does that make me that I pictured a man when the emphasis was on being a partner in a flourishing business and a woman when trust issues were brought up and the tone seemed more whiny? (Nocute, what makes you say assuredly that HELP is female?) Though I could be wrong, I'm going with feminine pronouns for HELP.)

Everyone has a choice here. Brother doesn't have to cheat, and he doesn't have to ask HELP to cover for him. HELP doesn't have to cover for him. Instead of asking him not to ask her to cover, she could simply announce that she's not lying for him any more AND THEN DO IT. Instead of worrying about work and income repercussions, she could take some responsibility, make money on her own, and get out from under this controlling asshole's thumb. Note that while I'm glad to call Brother a controlling asshole, I'm not letting HELP off the hook. He doesn't control her that much.

"My parents are also at their wits end." Which means that the parents are also of the mindset that all anyone can do when a family member is being a CPOS is run around in circles ineffectually whining. Reading between the lines here, HELP is afraid that if she doesn't lie for Brother next time, her parents will be put out with her for causing all that trouble in her brother's marriage, causing the divorce-- and the split in the business which puts everyone out some money It sounds like the dynamic for a long time has been one where the cute bad boy brother gets away with anything he wants while sister is put on the spot.

@29: "Nocute, what makes you say assuredly that HELP is female?

I'm not Nocute, but I assume she's referring to this part:
"It has also begun to affect the way I look at men. I've developed a lack of trust in those closest to me, seeing how easily a man can lie and expect others to lie and cover for him. (I'm currently in a relationship and pretty happy. I don't have trust issues with this person but this whole ordeal has left a bad taste in my mouth with regards to long term commitments, etc.)"

It would be unusual for someone to say that about a group they belonged to. The out-group homogeneity effect only targets out-groups, after all; a man doesn't judge all men by what he saw one man do, any more than a woman becomes a misogynist from seeing one other woman cheat.
@20 - LW said that some of the affairs were with people at work. If he's the boss and owner of the company, he's opening himself up to th risk of a lover becoming disgruntled and claiming sexual harassment. I'd argue that a boss having an affair with an employee is legally risky and therefore foolish.
@21. I don't think someone deserves any respect for generalizing about a group based on one individual, where we disagree it seems is that you think the more appropriate course is to ignore those comments, and I think someone should be called out on that.
As a woman who has been cheated upon, I think you should tell the wife. I agree to not go out of your way to do it, but if asked, say yes. When I started asking questions, I knew that something was up and I wanted to know. The gas lighting is horrible. It's so much better once you know. And when you're asking, you want to know. Before that, if you know someone is cheating, don't take it upon yourself to tell.
@20, yes, the brother is very much putting the business at risk.

As I previously stated, if he is finally caught by the wife, and she divorces him, she is probably entitled to half the value of the company in a divorce proceeding. Or half of his share of the company, whatever that is. In any case, a divorce would likely suck a big chunk of capitol out of the company, which could be fatal in itself.

And as others have pointed out, if he's cheating with women at work, he's opening himself to a huge sexual harassment lawsuit. If he's pressuring people at work to cover up his affairs, he's opening himself up to a sexual harassment lawsuit.

Even worse, if the LW is pressuring other employees to help her cover up the affairs, she herself might potentially be a party to a sexual harassment lawsuit.

There are so many ways for this to end badly. It sounds like a completely toxic work environment. Run, don't walk away.
@30: Yes, you beat me to it. Letter Writer is pretty clearly female, for the reason you mention. I'm surprised it took that long for people to (not) notice that it would be very weird for the letter writer to say:

"It has also begun to affect the way I look at men (of which I am one). I've developed a lack of trust in those closest to me, seeing how easily a man (which I am) can lie and expect others to lie and cover for him."

Aside from that, amen to what #18 said. Message to HELP: Listen up, Snowflake: women (of which you are one) are no strangers to the game of lying, cheating, manipulating and other crap behaviors, and if you think the reason you're a decent person is because of the genitalia between your legs, the real reason probably isn't the brains between your ears.
Whitey @7: The gender of the LW can be determined from the sentence "It has also begun to affect the way I look at men." Not "at other men."

Alison @13: Because the brother -- I know this is hard to believe -- LIED! Cheaters are also very good manipulators, at least this one certainly seems to be.

Xiao @26: Right on with your observation. Straight men complain about "women's" behaviour, and straight women about "men's" behaviour, when what they are actually complaining about is DATING/RELATIONSHIP behaviour. They just wouldn't know that their own gender does the same things, because they don't date their own gender.
"Straight men complain about "women's" behaviour, and straight women about "men's" behaviour, when what they are actually complaining about is DATING/RELATIONSHIP behaviour. They just wouldn't know that their own gender does the same things, because they don't date their own gender."

This is absolutely true. And is one of the reasons I eventually restricted myself to only dating bi women; it's not perfect, but it filters out a lot of the perspective-induced bigotry.
BiDanFan @36,

We don’t know for certain that he’s asking her to cover for him. All we know is that she is.

Other people lying does not cause me to lie. The LW is lying because she is lying, not because her brother lied.
Eud 30-- Good point on how LW must be female. I don't know how I missed that.

While it's not right or admirable to generalize the way HELP is doing, I do think it's understandable or normal. It's pretty known thing that children of alcoholics frequently grow up to find alcoholics for mates. You'd think they'd run in the other direction, but somewhere deep in the psyche, that's normal for them. While this isn't the same thing, I can understand how HELP could be shocked and upset as she processes learning in how many ways her brother's cheating is accepted. There she is involved in it herself, covering for him easily, not liking it, and feeling like a confused guilty mess.
@34 There are a lot of Ifs there, which can work both ways, for instance, if this couple have prenuptial agreement... . People posit a legal parade of horribles which they envision having incredibly high levels of success. I'm a lot more cautious about the possible outcomes for those cases.

At any rate, I think reiterate my point, which was picked up by @25 EricaP, that LW's letter suggest a level of immaturity. I see LW as having a valide emotion reaction to a distasteful situation, but I also see her searching for reasons to cover her desire to raise this issue with her sister-in-law.
@38, "I was coaxed to come back and work for him under the condition that I would no longer be asked to cover his tracks"

He actually IS asking the LW (and probably others, like his parents) to cover for him. My guess is that it happens in the form of "hey, if my wife calls, I'm in a meeting."
Jina @41: The letter is vague. She left three years ago partly because she “had learned about his multiple infidelities with women he worked with and with women outside of work.” Then she went back but “[I]t started happening again and again and again.” What’s “it” exactly? Him being unfaithful?

I get that if she happens to hear her brother having sex in the conference room and then his wife calls and asks to speak to him, it’s awkward. Especially the first time. But once she’s addressed this directly with her brother and made it clear that she won’t lie, then the next time “it” happens she says something like, “Yes he’s here but he’s with a friend right now and can’t come to the phone. If you call back in half an hour he should be able to take your call.”

If her brother is in fact asking directly as you suggest (though the LW does not say) then she answers, “Remember our deal.” And when his wife calls her complaining that he’s not picking up, says “I don’t know where he is. He left the office about an hour ago.”
@39: "While it's not right or admirable to generalize the way HELP is doing, I do think it's understandable or normal."

Yes, but she is also developing a complex about the entire subset of humanity that makes up her own dating pool. By demonizing 3 BILLION individuals over the actions of 1, she is actually hurting herself more than anyone else. The rest of the world will not suffer if she self-selects out of dating due to this misconception, but she will. She needs that "Oh, yeah, huh, that's pretty stupid of me..." moment for her own future good.
@41 That's what I was thinking. The correct response I think is "I'll tell your wife that you said you were in a meeting and if she asks any particulars I'll say I have no idea with whom or about what you are meeting."
44-- No, no, the correct response is "He's in the conference room. I'll get him." Then you knock on the conference room door, and if he screams "What? No! My wife? Don't come in!" You turn to the phone and tell the wife "He said "What? No! My wife? Don't come in!"" Bonus points if you tell her he sounded out of breath and had the new-hire in there with him. Better yet, just go in while he's mid-fuck, hand him the phone, and say "it's your wife." THAT'S what not covering for someone looks like.
I'm with you Crinoline@44...put her on Facetime and walk in with cameras blazing. Oops! Boss! What the hell are you doing!? You might even win a prize on America's Funniest Home Videos.
Crin for the win on this thread.
Am I the only one who's driven fucking nuts by a letter that's ruined by vagueness about the writer's gender/orientation when it would be relevant? This LW mentions losing trust in men, but we can't really tell whether that's referring to his/her relationship with a "person". FFS, don't make me read the letter three times over to try to figure out if there's a subtle clue in there. Just fucking state your gender and orientation up front so we know what the fucking pronouns mean and don't play this coy "person" shit.
@48 Surely the LW's gender is actually pretty irrelevant to any advice that is specific to the situation they're asking about? Sure, if you want to comment on their reaction to the situation you can bring gender into if if you must, but it's not pertinent.

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