Dear ILX, I have a boring tl;dr question about my job and how not to be a stupid, annoying co-worker, and I'm hoping you can help.

I've been annoyed lately because my coworker and I are meant to cover for each other's absences, so I've had to ask him before I book any leave, but when he's booked leave he hasn't even told me. This combined w/ him planning further ahead than I ever do means he's beaten me to a few dates I would've liked off, plus I wasn't allowed a week I wanted off for unrelated reasons.

So I decided to book a week off way in advance and be like him and not even ask, because it is the bf's birthday that week and he will be going back to his old hometown to visit friends and relatives. Half an hour later, coworker goes to the boss to book the exact same week. The boss comes out to tell us we can't both have it, and I say "uh, I could make do with the first two days I guess", and coworker says nothing.

So, my boss OKs my 2 days, and then I find out that my coworker wants to go to a wedding on the second day, and both of us are travelling far enough that we'd probably need both days off.

I emailed my boss to say that if we could both have leave that would be great, but if we're not both allowed leave I want him to take it, as his reason is much more important. My boss just replied that I should have it. And now I feel like an asshole, because my boyfriend's birthday is not a round number and I see him every day, so, y'know, it'd be nice, but it's no wedding, you know?

Well, tl;dr, but if anyone made it this far, what do I do? How can I change my boss's mind? I cd possibly get the manager of the project we're meant to cover for each other on to say they can do without on-call support for 2 days, but involving third parties to overrule my boss is NAGL, right?

"Dear boss, I want to stay on good terms with co-worker and his need is greater than mine. Can we switch days so I don't look like villain?"

so I've had to ask him before I book any leave, but when he's booked leave he hasn't even told me.

This is the only thing you need to think about.

I think the burden to try to get an exception made is actually on yr colleague? You've been more than fair, it sounds like, and no higher ups have noticed(??) that you weren't getting a fair deal from the other guy, who wasn't checking dates with you. Sometimes when you're in a position of strength or having "won" something, an egotist might be comfortable up on that perch but someone genuinely not self-promoting might not be. You don't have to apologize for coming out a little bit better this time!

It can actually undermine you with others, not to be comfortable "winning" things. It's weird, right? Because you don't want to be or become the asshole that others often are to you! But sometimes you can be comfortable getting what you deserve.

I just feel bad because I would never normally book leave 3 months in advance, and this is not a particularly special occasion, and I only really did it out of... spite, almost.

In fact, if I let myself get really paranoid, I can convince myself that my boss knows this, and wants me to look the villain (as WmC aptly puts it). Or maybe he has in fact noticed that I got the short straw the last couple of times and is being nice. Or maybe my boss is not letting emotions come into it at all and is being purely first come first served, of course.

I wonder if unapologetic winners can also manage not to second-guess and psychoanalyse everyone else? That might be a good skill.

I've had to ask him before I book any leave, but when he's booked leave he hasn't even told me.

I wouldn't even second-guess taking the time off, given this is the way he has behaved.

This used to happen to me all the time: a colleague who I had to cover for (although not the reverse!), who made more money than I did and could afford to travel and plan/buy tickets ahead (unlike me), used to ask for time off that was still MONTHS away and of course since she was first, she always got it.

I didn't like her to begin with, so I can't say that her vacation practices really helped. Enjoy your days off.

Eating dry grape nuts at my desk: how do I rate as a co-worker?