Oh boy, fluther. Can you help me with this friend problem?

Go and tell him the truth. He’s your friend first who’s suffering because of a person who doesn’t deserve to be in his life at all.

Disclaimer:

I don’t know what you should do, as I’m not you and haven’t met any of these people, of course, as you know, but as you know this and are asking anyway, I will imagine myself in such a situation, and say what I would do in the situation I am imagining.

Check-in:

First, I would meditate and re-assess it all and ask my gut and intuition about it. Assuming I was still confident of the opinions as you describe them, I’m pretty sure what I would do is this:

Suggestion:

I would first consult with my wife, let her know everything, and what my suggested course of action is, and make sure she agrees. My relationship with my wife would be most important, and so I’d want to be entirely open with her and ask for her approval and input. Also because Tom was her friend first, and she is probably more invested in it than I would be, I would defer to her wishes and, because I would respect and defer to her wisdom in such matters.

What I’d propose is that I, or my wife and I, get together with Tom, and talk to him to be supportive, ensure him that we’re there for him no matter what happens with Jan, and feel him out and see if he was interested in perspectives, advice and/or information. It’s possible he would not want to talk about it or say something to indicate there were an issue, but assuming not, I’d offer the facts about what Jan has said and, if asked, my perspective/opinion on Jan, and probably (if he wanted to hear it) that he’d probably be best off getting himself well out of that relationship.

Sounds to me like Tom should definitely get out of it, and hearing what you’ve heard from Jan may help him to make up his mind about that.

She put you in an awful spot. She shouldn’t be confusing in you. It is a terrible burden for you to have to hold these “secrets.” She might be telling you on purpose knowing you are a risk and might talk.

My inclination is don’t say anything, but if Tom asks you something point blank to your face, don’t lie.

My opinion doesn’t really mean much, because I’m not really in the situation like you are, but what I suggested is along the lines of what I do in similar situations.

You could tell her next time she starts venting to you that you prefer not to talk about it, because you feel put in the middle, or put in an awkward position, or however you would describe it.

Tight situation.
I think that given how hard he is trying, he would not appreciate outside info or advice.
It is a tempting move, like swatting a fly, but it could get two people angry with you.
If you MUST do something, I would say do it on the sly. For instance, if you know of something she is keeping from him, mention it, in front of both of them. Once you do, apologize, oh sorry, I wasn’t supposed to say anything.
It sure sounds upsetting for you and your wife, but it is just so risky for a friendship to get involved in someone else’s relationships.

Can you expound on the relationship dynamics between you and Jan at your job since you have to work with her? If you were not coworkers it would be a no brainer for you to get involved.

You’re in an exceedingly difficult position, and I feel for you. If you speak out or if you don’t, friendships and relationships are at risk, and someone will suffer.

One of my test questions for hard choices is whether it’s reversible: if I don’t do it now, can I do it later? If I do do it now, can I undo it?

Another big one is whether I can live with the consequences. That one’s often hard to gauge, but I try. And of course that also goes for consequences to others—including some whose choices might be preempted by what I do.

There’s also the fact that in this situation, it may not be possible to tell Tom anything. Instead you might just engender his enmity.

Someone close to me has recently gone through a very bad breakup. I have always made it a strict policy not to get in between a couple and in particular never to interfere in my sons’ relationships. He now sees things he couldn’t see before, including some things I already knew, and he wants to know why I didn’t tell him. “Because you couldn’t have heard me; you wouldn’t have believed me. It would only have alienated you and probably even driven you away, and bound you tighter to her.”

And maybe Tom already knows. People usually don’t thank you for exposing their denial. Instead they resent you for it.

In your place, I think I would cool my relationship with her: “I’m sorry, Jan, but you know Tom is my friend. I just can’t hear any more of this. It forces me into a place where I don’t belong.”

And it is a place where you don’t belong. Tom has to deal with this as best he can, in his own way. When the time comes, just be there for him, but don’t try to push him to get there.

And don’t let Jan use you to flagellate Tom.

Whatever you do, don’t do something you’ll feel you have to conceal or something you’re ashamed of. That’ll come back to haunt you when the rest of the truth comes out.

As always, this is nothing but a personal opinion, offered with goodwill but no assurances.

The little voice inside my head is almost screaming, “He has to tell Tom!”

My suggestion (only because you’re asking) would be similar to that made by @Zaku above…discuss it with your wife, then if she agrees, talk to Tom. Don’t let it affect your relationship with your wife.

If you do decide to talk to Tom about it, you and your wife may want to see him together. If they are separated, it shouldn’t be an issue.

The conversation might start like this:

Tom, the wife and I have been friends with you for a long time, and we value your friendship, and care deeply about your well being. I am (We are) really reluctant to get in the middle of your relationship with your wife. I (We) know it’s hit a rocky patch that has resulted in a separation. As you know, I work with Jan. She’s said some things to me that I think you should hear, if you would like me to share. Of you would rather I (We) stay uninvolved, I (we) will respect that.

If he prefers that you not involve yourself any further, I would respect that, and tell him the offer will still be there, should he ever change his mind.

If he prefers to hear, I would be as open and honest about it as possible.

Let Tom have control over your involvement

I would be very cautious. For example: Tom, I have some reservations about this, would you like to discuss it?

Been there and done that. I always find most of the time you lose your friendship with someone who divorces. Of most of my divorced friends it seems they never want to be with people who they use to hang out with as a couple. And the chances get less if they feel embarrassed by having been taken advantage of. Even if you tell him all this stuff, he may appreciate being told on one hand but feel like a fool every time he sees you. I had a friend like that years ago. She confided in me about her cheating husband who was actually our friend first. But long story short, after they split she stop coming around and we certainly didn’t want to see him. He did some really crappy stuff to her and she was so devoted him and did above and beyond to keep him happy. But he was selfish as well. My husband worked with him but didn’t know of his cheating. He was cheating with someone from work. I always felt she dropped our friendship because she thought my husband did know and kept it a secret. She use to go on about how she must’ve been a laughing stock at his job.

My point is whether you tell him or not, he may still feel a fool and you may still lose a friend. So maybe you will at least clear your conscious. But do discus it with your wife first. Maybe find a way to break it to him without making him feel like a fool.
But there is also the possibility that his wife is using you to break it to him. She sounds pretty gutless so this is a possibility. Also could it be she is hoping to have him push for the divorce so that she can get him on alimony?

My two cents: Stay away from this. Do not get involved. You’ll get sucked into a place you don’t want to be.

As much as you are friends with the guy, no good can come of you getting involved.

I think I’d start by not allowing Jan to talk to me about personal stuff. Redirect redirect redirect. If necessary, tell her straight out that you can’t listen to her talking about her relationship. It is at the very least inappropriate for colleagues to discuss personal matters. If she pushes let her know you are not qualified to talk about these matters and gently encourage her to seek professional help. That may get her to back off .

I’d also suggest talking to your wife about what’s going on – she’s your spouse and you need her support with the awkward situation you’ve been put in.

Whatever is going to happen to Jan and Tom is going to happen without your input.

For some reason Jan has glommed on to me. During the wedding preparations she came to me almost every day to complain about Tom’s family, how she didn’t want the wedding and I was there to counsel her (Believe it or not, I used to be a counselor, I have DBT training and I can be incredibly perceptive and help people see things more rationally.) Ever since then, she always comes to me with her issues, and as always I give her my opinions and I truly try to help her with her overwhelming emotions.

I have considered all of your opinions and I have talked to my wife. She is at the same point I am. We want to do something, but feel like we shouldn’t get involved; she misses her friend.

I am definitely leaning towards staying out of it. My wife and I are entangled with them in many ways. Our landlords are friends with Tom and Jan’s family. (The Jewish community in the San Fernando Valley, CA are very close knit and the families are all intertwined.) If things go badly, it could effect my wife and I in many ways.

I knew my little fluther would lead me to a decision.

If I were in a similar position, and this is not a rented relationship but one with a ring on it, II would impart to inform him if not bluntly he needs to reconsider if he wanted to remain yoked to a woman who is not evenly yoked with him. If he is a true friend to do nothing would show the level of that friendship, if he were in need of a lifeboat and his mate was telling you she would eat al., the food, hide what she could from him and at some point toss him overboard, and you left him thinking it was going to be smooth sailing, you are showing her to be a better friend than your friend.

If I was Tom, I think I’d really appreciate it if you let me know what is going on. I think you should talk to him. If your seeing something that could potentially have a negative or prolonged impact on your friend then its your right and duty to tell/warn your friend. Maybe talk to your wife and decide how you’d like to go about telling him since she’s known him longer she may know what approach would work best with Tom.

And if for some reason you decide it may not be a wise decision to disclose this information to Tom then at least consider telling Jan how you really feel or asking her politely to shut her pie hole and leave you alone for you are on ’‘Team Tom’’.