Dear John: Ex Boyfriend. Current Boss.

Wednesday, April 11, 2012

John Simpson, GoLocal Advice Columnist

What’s your problem? Write to John at [email protected].

Dear John,

Ugh, this is terrible. Several years ago I used to date a guy I worked with. It was promising at first, but when it ended, things really blew up. I basically found out I was dating one of these guys who has three or four women at any given time all thinking they’re special. Like, expecting a ring special. He was such a liar I think he believed his own lies. Seriously. Anyway, the company we work for is pretty big, so our paths didn’t cross much for a long time. It was fine. An unpleasant experience that I put behind me. But for a few months now, he’s been my boss. He’s actually pretty good at his job (apparently), and he’s well liked in our company. He was promoted and due to some internal restructuring, now he’s my direct boss. And it’s awful. He knows I don’t like him, but he has adopted this demeanor of being so professional and pleasant, he really seems crazy. And a couple of times, he has made the most subtle digs at me in meetings – the kinds of things where no one would even notice, but I got the message. He’s that kind of guy. Very manipulative and vindictive – even if it’s just vindictiveness at being made to feel uncomfortable because he knows you know what he’s really like. It’s really adding to my already high stress level. I don’t want to find another job. I love this one – or did until this all happened. I’m not even sure I can, anyway. I knew dating a co-worker was a mistake, but it seemed so minor at the time. Now every day I’m on edge. Any advice?

Sincerely,
Sorry All Over Again

Dear Sorry All Over Again,

It sounds to me like your anxiety about this is making the situation more unmanageable than it really is. That’s not to say your anxiety is hard to understand, but perhaps it would be allayed somewhat if you felt like you had a little more control. So the first thing I would do (if you haven’t already) is to talk with him privately to tell him that, while the two of you share an unfortunate history, you have no intention of letting it interfere with your working relationship and you hope he feels the same way. (It just seems odd to have this hanging in the air between the two of you without addressing it directly.) Hopefully, that’s what he wants to happen, too, and he’s not so stupid as to try to use his new position to make your life miserable. Until you’re completely certain that’s how this is going to go, though, I would protect yourself by documenting all your interactions with him so that if you ever have to provide evidence of a pattern of unprofessional behavior, you’ll be ready. For now, do the best job you can, be cautiously optimistic, and see how it goes. It may be a bit galling, but with any luck, he’ll be such a good boss that he’ll get another promotion and you won’t have to deal with him any more.

Dear John,

Is it EVER okay to date your brother’s ex-wife? I’m in my fifties; I have a brother who’s just a couple of years older. We’re both divorced. His first wife (first ex-wife I should say) just moved to the city I live in. They’ve been divorced almost twenty years – a very long time, but it was really acrimonious when it happened. Very, very ugly. I don’t think they even keep in touch any more (no kids or anything). The thing is, I really used to like her. We always got along well. I’ve got nothing going on romantically and no one I’m even interested in right now, so I thought I might call her up, catch up and see what happens. I’m not sure how to deal with my brother, though. I know he’s going to hate the idea of this. He’ll claim he has my best interests in mind, but that’s not true. He’ll just want that part of the past to stay dead and buried and this will bring it all back to life, or it could. We get along well, but there’s always been a rivalry there, too, so no matter how his marriage ended, part of his problem is going to be as simple as, “That used to be mine, so you can never have it, even if I don’t want it any more.” So I don’t know, maybe it wouldn’t even be worth it. If I do it, though, when do I tell him? Right away? Don’t say anything unless it looks like it could go somewhere? What’s the “right” thing to do here? I’m a little too close to it.

Signed,
Ex-Brother-In-Law

Dear Ex-Brother-In-Law,

Let’s start with your final question. You don’t owe your brother an accounting of your dates. I might feel differently if they were recently divorced, but twenty years? I’d say enough time has passed for her to be fair game. And I’d let him know what’s going on whenever it becomes “serious,” and you can define serious however you want.

As for your more general question about whether it’s ever right to do something like this, yes – your situation is a good example. There’s nothing wrong with asking this woman out. And that simple fact has nothing whatsoever to do with how your brother will react to it. The way you’ve described him, there’s an excellent chance he’ll fly off the handle (although he may outwardly claim not to mind to deny you the power to upset him). You can’t control how he’ll react; you can just be confident that you’re not doing anything wrong. Whether all this is worth the drama it will cause is your call to make. Just be honest with yourself about your motives: if you do ask her out, be certain it’s not to stick it to him (even a little bit), and if you don’t, be sure it’s because you don’t want to, not because you fear his wrath.

Dear John,

My wife recently befriended a woman who’s quite well off. Financially, we’re fine – not struggling, but we both work hard to maintain the life that we’ve built. But this woman and her husband are in a whole different league. They are people for whom money is truly no object – maybe it would be if they wanted to buy a professional sports team or something, but for living in our nice college town it certainly isn’t.

The problem is, my wife is kind of realistic about where we stand financially and kind of not. Because we have a nice house, nice cars, etc., I think she sometimes lulls herself into thinking we have more money than we really do. I handle the finances and I know better. Like I said, we have a great life and I feel very fortunate, but we don’t have a lot left over. Only now my wife has started talking about doing things her new friend and her husband do, like taking lavish trips a couple of times a year, buying a second home (a “small” one!) – even her shopping trips with her friend place an inordinate amount of strain on our budget. The thing is, she can’t discuss these things rationally. When I tell her she can’t spend so much, she takes it as she can’t be friends with this person. Of course I have no problem with their friendship. The only thing I have a problem with is pretending we can do the same things they can. We just can’t. When I point this out, though, she gets very upset and it just turns into an argument. I would appreciate any suggestions to help her see my point of view.

Sincerely,
Strained

Dear Strained,

I have no suggestion that will help your wife grow up. Not that it’s exactly rare, but insisting on buying things you can’t afford demonstrates a lack of maturity and a warped set of values. You have to emphasize to her that your household runs on a budget and you’ll be happy to share the details with her. She’s free to spend as much as she likes of the money budgeted for frivolous purchases, but beyond that, there’s simply nothing to spend – not responsibly, anyway. It sounds like your wife thinks her friend likes her for what she can buy rather than who she is. I bet that’s not actually the case, but counseling may help her better understand why she would think such a thing.

John is a middle-aged family man from Providence, Rhode Island. If you learn from your mistakes, he’s brilliant. Write to him at [email protected].