A reader writes:

I started a new job just over a month ago. On my first day, a coworker — Kevin — asked if I would like a doughnut from a popular bakery near our office, as he was headed there anyway. I said yes, and he brought it. (He got my order wrong, but oh well, still a free doughnut!)

I thought he was just extending a nice gesture to the new employee, and that would be the end of it. But had I known what would happen next, I never would have accepted the doughnut — because it opened the floodgates of unsolicited food items.

At least five times now Kevin has brought food I didn’t ask for. I say no to the food every time and have outright asked him to check with me first before bringing me anything, which he verbally agreed to, but he has not actually stopped bringing me things unprompted. Most recently today, he slammed a big bottle of iced tea onto my desk, and demanded to know why I didn’t want it when I turned it down.

I’ve told him I have health-related dietary restrictions (not just a deflection tactic, some foods make me pretty sick), which also hasn’t deterred him. I’m at the point where I’m not really able to be polite about it anymore, since I set the boundary and he seems to have no intention of respecting it, despite me sticking to the “no.” My work station is freely accessible to everyone, so I can’t prevent him from bringing me things by shutting an office door.

I’m so annoyed but I feel bad for him at the same time, because my impression is that he badly wants to be liked by me and our other coworkers, but he’s so clueless that his overtures just have the opposite effect.

Is this something I can take to my boss? She also manages him but I feel almost silly bringing this issue to her, especially since I’ve only been working here for a month. I’m worried she’ll think I’m being too harsh/judgmental, or that I’m trying to stir up trouble. Any advice would be much appreciated.

I wrote back and asked, “When you told him you had dietary restrictions, what did he say? And have you noticed him doing it to anyone else?”

He acted like he understood when I told him about my restrictions and asked what kinds of things he should avoid, I told him it’s kind of a long list so the safest bet is always to ask me first. He seemed to agree but then brought me a brownie without asking three days later, which I turned down.

I’m one of the first people you see when walking into the office, so when I inevitably say no to the food, he brings it straight to someone else. It seems like he wanders around until he finds someone who wants whatever random food he has. I asked another coworker about it and she somewhat sheepishly admitted she’ll usually take what he offers but then throw it away later.

As an even weirder side note, on my first day when he brought me the doughnut, he also asked my manager if she wanted one; she told him no. He proceeded to bring her one anyway.

What on earth.

I’m sure you’re right that Kevin is desperate to be liked by people — this is very much currying-favor behavior — but doing the exact opposite of what people have repeatedly asked from you is a weirdly bad strategy for that. It seems like he picked up on the idea that bring food can be a gesture of warmth (it can be!) and he cannot let it go, no matter what the people he’s aiming it at tell him.

So, you’ve got two options here:

1. You can call him out on it more assertively: “I asked you not to bring me food anymore, what’s up?” Or, “I asked you not to bring me food. Please respect that.” Neither of these would be rude, but you might feel rude saying them — it’s a level of bluntness that you normally don’t need to use with colleagues and it might feel like a lot for a work relationship. But his aggressive food pushing is a lot for a work relationship! It’s not inappropriate to tell him bluntly to stop when he’s ignored politer wording.

2. If you don’t want to do that, the other option is to just consistently say no every single time. Don’t ever give in — even if he shows up with an enticing item you very much want — because if you do, you’ll be training him that if he asks enough, sometimes you’ll say yes. Stick with “no” every time. Feel free to sound bored or even annoyed when you say no.

If he again demands to know why you’re saying no like with that iced tea (!!), you can say “because I don’t want it” or “because I asked you to stop bringing me food” or “because I asked you to stop bringing me food and it’s getting really weird that you won’t.” (That last one feels kind of mean, but you have standing to say it because it is getting weird. And after something passes a certain level of weirdness, it’s arguably kinder to just tell the person that. That level has been passed.)

I don’t think this is worth taking to your boss — not because she’ll think you’re being too harsh or trying to create trouble, as you worried about, but because ultimately it’s a pretty small interpersonal issue that most managers will want you to deal with by just telling Kevin no … and also because he’s apparently doing it to everyone and she probably already knows about it. (If the behavior were worse — like if he were leaving food items on your desk that he knew you were allergic to or if he starts throwing more of those iced tea tantrums — my answer would be different.)

If you weren’t new, there would be more room for going to your boss and asking what the F is up with Kevin’s aggressive food behavior, but as a new person I’d handle it on your own for now.