The Relationship Judge: To Tell or Not To Tell

It’s a brand new year of juicy relationship issues and here at The Relationship Judge, we are ready to go.  No problem is too small to be judged – keep them coming! Today’s Relationship Judge is fairly straight forward, but kind of a crazy situation.  Which is good because it’s Friday and I could use hearing about someone else’s “craziness” on a Friday.  Here we go…

The Facts:  Lesley (I’m using that name in honor of one of our favorite Bachelor contestants this season), an old friend of mine, wrote in as she’s very stressed and needs advice.   Lesley works full time as a compliance associate at a bank in New York City.  She’s very close with her brother and his girlfriend, Whitney, who is Lesley’s co-worker.  Lesley is responsible for introducing them and they have been dating for 8 months.  Recently, however, Lesley has learned that her brother (who has a wandering eye) has been pursuing someone else behind Whitney’s back.  Lesley has urged her brother to end things with Whitney (who is already designing her engagement ring at various websitse during work) but he has not indicated if and when this will happen.  Lesley is very worried that her brother won’t do anything and the relationship will get carried out indefinitely.  She’s also worried about Whitney finding out about “the other woman” and particularly, that Lesley knew about it and didn’t say anything.  Being at work could get very awkward and stressful very fast.

The Question: Should Lesley indicate to Whitney in some way that her brother is cheating on her?  Should she get involved at all?  What happens if all hell breaks loose and Lesley is still forced to work with Whitney?

The Relationship Judge Says:  YIKES!!  This is a tough one.  Do you remain loyal to your cheating brother and keep his secret or do you fess up your knowledge to a good friend?  First off, just as you should probably never date anyone from work, for the same reasons, you should also heavily discourage a close family member from getting romantically involved with a co-worker.  That’s just a recipe for disaster, particularly when things go south.   Having good, solid friendships with co-workers is essential for a number of reasons.  Co-workers can become just like family – you probably see them more than your actual family depending on your job, so treat them kindly and honorably.

As for your question, though, there’s no easy answer here, but clearly, if Whitney rightfully thinks that she is in a committed relationship with your brother, then your brother is the “wrong” one here.  I would go to him this very second and give him the option – either he ends it or you’re telling her the truth.  Normally, I’d tell you not to get involved, but Whitney is your friend and you WILL be in the middle of it to some extent and you don’t want the middle of it to be at work.  Leave all that drama outside.   Be prepared for Whitney to put some distance between the two of you for the immediate future even if you are physically working near her.  It’s not fair – you’re just the sister to the dumper, not the actual dumper.  Still – she’ll need time to heal and get over it.  Try not to share too many details of what you did or didn’t know  – that will only get you in trouble and truthfully it doesn’t matter.  The bottom line is they needed to break up and you made that happen a little sooner.

PS – Maybe you can set her up with someone else when she’s ready?? Or nominate her to go on the next Bachelor?

Your Turn: Should Lesley get involved here?  Is it her job to let Whitney know what’s happening or should she stay out of it?

Have a wonderful weekend!! We are starting a dog training class for Wally on Saturday and on Sunday we have a dog birthday party.  This is not a joke.  Someone rented out a private room for a dog’s first birthday and we got an invite to join the festivities.  I hope Wally’s missing balls can handle the excitement.

Until next time, you can receive updates if you “Like” my Facebook page ( or “Follow” me on Twitter (@OfficeStace).



  1. Yikes indeed! This is a tough call and I feel for Lesley in this situation. Stacey you mentioned that you and Lesley are old friends, so I’m wondering what you know about the brother’s personality…?

    Anywhoo…I find this whole circumstance interesting (as I’m sure we all do). Lesley clearly set up her co-worker with her brother in good faith hoping the two would hit it off. If after only 8 months we have a brother who is cheating and a girlfriend who is shopping for engagement rings…then clearly the two are not even close to the same page on this relationship. However, before I started mind reading, I think I would first have a come to Jesus convo with my brother to say…WTF are you doing, thinking, etc. This girl is crazy for you and if you don’t feel the same way then cut her loose immediately. I would let my brother know that leading Whitney on is just plain cruel and it doesn’t help when I have to work with Whitney everyday knowing how you feel and how she feels….so man up already! Another possibility is that brother just sowing some final oats, prior to making a deeper commitment to Whitney (not soo unusual for many men). In any case, I would want to first know what his mindset is all about prior to posing the ultimatum….What are his true intentions where Whitney is concerned? Lesley – pin your brother down on this…he’s sounds like a potentially squirrely guy who will wiggle out of uncomfortable convos whenever possible. Don’t let him out of this one!

    What also occurs to me is that he may in fact be hoping that his sister Lesley will break the bad news to Whitney, letting him off the hook entirely and making his getaway that much easier. Don’t let him get away with this either Lesley! Your brother is the one in the relationship with Whitney and he needs to take responsibility for his behavior. Cheating can be indicative of a variety of things, one of which is a passive aggressive move to end a relationship when you don’t have the cajones to do it yourself.

    Of course the rub is that you work with Whitney each day….and set her up with your bro who is now acting like a jerk, possibly making you feel a bit guilty and/or protective of your girlfriend. However, I maintain that it is still up to your brother to take action, not you. If he’s no longer interested in Whitney, he needs to tell her himself. You can certainly encourage him and even put some pressure on him to be accountable. But you breaking the news….just lets him off the hook and puts you and your friend Whitney into an even more uncomfortable situation.

    Meanwhile, perhaps you can give Whitney some subtle hints that could potentially help her to become more aware of your bro’s bad behavior and their obvious incompatibility. I can completely understand your desire to get this uncomfortable situation over with, but again, I don’t see much good coming from you acting as the messenger.

    Best of luck!

  2. Lesley wants what is best for her brother.
    In time, it sounds like the brother will approach Whitney and tell her how is feelings may be changing.
    Whitney will probably ask Lesley for advice.
    At this point Lesley will be brought into the picture, and it will be a difficult day when that occurs.
    I suppose the best thing for Lesley to say is,”I don’t want to get involved, this is something the two of you must resolve”.
    In time, the right person will come along for Whitney, but that is “easier said than done”, but it will happen.

  3. Stacey, I wrote my response before I read yours.
    I really like what you said, and it actually made very good sense to go the brother and have him “do the right thing”.

    Love your blog, advice, videocast, the whole package!

  4. Hi Stacey,

    Here’s my advice.

    Lesley, should stay out of it. Her good intentions could backfire. Then she might have both her brother and her co-worker angry with her. Let me explain.

    Tough Call has a great point: the brother should (must) take responsability for his decisions. However, Lesley is *assuming* he is *cheating*. Perhaps Whitney *has been informed*. Lesley can’t possibly know all that this couple has discussed. Maybe her brother has tried to make it clear that he doesn’t want to make a commitment as of yet. Possibly Whitney is fantasizing and not really listening to Lesley’s brother.

    Or could her brother be getting *cold feet* because Whitney is too intense or stiffling? Wouldn’t it be wiser *not* to pressure him too much if he already feels pressured???

    What *does* concern Lesley is her relationship to her co-worker. *That* is what she should discuss with her brother. She should let him know of her predicament. If her brother is unsure of his feelings for Whitney (at times feelings are conflictual and complicated) *surely* he knows his feelings for his sister.

    In turning the discussion towards herself, Lesley’s brother will feel less threatened about discussing the situation. He may really open up. It’s understandable that he doesn’t want his sister to be meddling in his personal life. ! (Is Lesley a *big* sister, btw???!!) He may be more sensitive to her if she explains *her problem* rather than his.

    There are always 2 sides to every story. Don’t be too harsh on your brother Lesley. He may be considering his relationship with Whitney much more that you realize. If he feels too rushed, or pressured but is considering a serious relationship with her, he may need more time.

    Men consider the financial, social, and moral commitment to marriage. It’s a really *big* step. It isn’t just about feelings. It may just be a matter of his needing more space or more time. Let him know you are on his team, that you are very concerned for Whitney’s heart getting broken BUT that *you* need to know what *you* should do.

    Best wishes for a swift and amical resolution to your dilemma.


  5. I have experience with this sort of thing, having several older, and some younger brothers. It looks to me like Whitney is moving to fast, and Leslie’s brother is thinking about bolting.

    My advice is different but it comes from experience. Get yourself completely out of your brothers relationship. Its his and Whitney’s to deal with not yours. You don’t want to choose him or Whitney. Yes you may need to get along with Whitney on the day to day stuff. But when the whole world is going crazy one day (and it will cause thats life!) you are going need your family.

  6. I agree with Stacey’s idea but Tough Call makes an excellent point as well. The blowout should clearly fall in the lap of the brother, not Lesley. Perhaps Lesley could still give the brother an ultimatum but rather than TELL Whitney the truth, she could arrange an outing where she & Whitney “bump into” the brother and this other woman. This accomplishes the same goal but puts the brother in the line of fire.

  7. The answer is clearly tell her, even if only for health concerns. Does no one think about this at all? Some people have diseases and if he is cheating.. she needs to know. There shouldn’t even be a question about it. And it’s not a tough call.

  8. She needs to be told. Of course, the brother should be the one to do it. Put the pressure on and if he doesn’t, figure out a way to do it when he is present so he can be adequately confronted. Totally agree w/ the Anon. Hello STDs! They are rampant and if he is sleeping around she could be in danger. Not to mention the morality of the whole situation. Put yourself in her situation. If my friend knew my boyfriend or husband was cheating and didn’t tell me, let’s just say we are NOT friends. This ‘blood is thicker than water’ idea is crap when your blood is acting like an ass. That doesn’t mean you protect a person whatever the circumstances. Someone earlier said she shouldn’t tell bc you never know what’s going to happen and you’ll always need your family by your side. That’s true, but I guarantee he’ll be more responsive if you hold him accountable but forgive him. Of course – don’t push him aside bc he did something wrong. We all mess up at times and we wouldn’t want to be shoved aside in a moment of weakness either. Tell him you are doing it for his sake too – bc if you really love him you don’t want him to screw up a potentially great relationship and regret it later. He may be pissed off for a moment, but when the shit hits the fan and his family is still there for him, he’ll realize his offense on some level and be thankful for a sister who isn’t afraid to be honest with him. That’s my 2 cents, for what it’s worth.

  9. One more thing – true – you may lose a friend, but deep down she’ll know you were just trying to do the right thing and she’ll be thankful for it sooner or later.

    I have actually been in a similar situation myself. It wasn’t my brother, but my bosses, when I was a nanny. The father was trying to hit on another nanny for the family and it really bothered her but she was scared to tell the wife. I told the wife bc it was the right thing to do. Of course she fired my friend (who was planning to quit anyway bc it was just too awkward), but she was very thankful to me for being honest. In the end, it saved their marriage. I know these 2 people aren’t married, but who knows? You could save their relationship and they could move on to get married and have a great relationship in the long run. I for one could never, ever have forgiven myself if I didn’t report the situation I was aware of to the wife and they wound up getting a divorce bc of it. Of course it doesn’t always work out for the better like that, but you never know what’s going to happen if you don’t do the right thing. In the end, you won’t have to second guess yourself when you’ve done what is right.

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