Approach a coworker-friend about being nicer to his friends

Question

TLDR: My coworker makes unkind jokes about someone else to build rapport or support friendship with me. This makes me uncomfortable because it is outright mean and has noticeably hurt the teased party more than once.

Background:

I have a coworker who I have become friends with. He feels very close to me and (over)shares a lot of his personal life with me. He also feels very free to ask very personal questions about my life and frequently crosses my normal boundaries for coworkers and men (I am a female 10 years his junior). I am working on getting him to recognize that when I deflect his questions and statements I am attempting to avoid a topic he has brought up. Usually, his response is to ask again even more directly, which is uncomfortable at best. He has told me several times he believes himself to be on the autism spectrum, which I believe contributes to his ignoring my conversation signals. I am close enough to him to spend social time at his house and house-sit for his pets. (Read: coworker is harmless, married, and acts more like he's my age.)

The Problem:

Recently I have noticed that one way he likes to build rapport is to make fun of my boyfriend who is also a coworker, and typically the kind of guy to clown around and make jokes. On one recent occasion, I made a joke of some sort, my boyfriend thought it was a little funny, I explained the pun in the joke, and then he laughed more, understanding the real joke. Our older coworker then chimed in a euphemism about the last horse crossing the line and I didn't understand the phrase. When he clarified he said something like the stupid people laugh last. I thought that was a very mean thing to say. Being the non-confrontational person that I am, I attempted to deflect by saying "I usually laugh last" which is entirely true, but because I have a hearing loss that causes me to miss jokes. Then instead of allowing me to shift the conversation to myself he basically drove home the point that he thought my boyfriend was stupid and should have gotten the joke.

What I would like to achieve:

I don't think he actually thinks my boyfriend is stupid. He thinks very highly of the both of us. But because he works closer with me and is closer to me, I think that my boyfriend is seen as a mutual punching bag to bond over. How can I make it clear that this behavior is unacceptable? In the past, when I have called him out on very minor offenses against coworkers who were not offended in the moment, he just grins and says "I know, I'm a terrible person." and makes a big joke out of it. In the past, if I have declined offers to hang out or said I'm busy or talk about an event I'm excited about, he will make it very obvious he is hurt that I won't make every effort to involve him and will guilt trip me while making a joke about it. I would like to tell him he shouldn't make fun of someone I care about, and for him to take it seriously with no joking and guilt-tripping.

Answer 1

He has told me several times he believes himself to be on the spectrum

Being on the spectrum does not give you a free card to insult people after being told that this is inappropriate and unwanted - especially at the workplace. Also note "he believes himself", he isn't even officially diagnosed.

---

he just grins and says "I know, I'm a terrible person." and makes a big joke out of it

Don't let him make a joke of it. If he says that, do not engage with this behaviour. Do not laugh along, do not smile. You want him to know that you think this is not funny and that you want him to take this seriously.

Listen , this is not a joke to me. You are actually hurting people and the working atmosphere with this behaviour. Can you please stop?

Exclude the please when this comes up again and again.

---

he will make it very obvious he is hurt that I won't make every effort to involve him

Whoa, what? You don't make every effort to involve him? So your life mission is now to be the caretaker of this person? Hell no.

You can not let your life be determined by this guy and if you feel that he would not be a good fit for a personal event then you don't have to invite him. If he asks for a reason you can tell him that in the past he has caused people to have bad experiences because of his behaviour.

You should of course give him a chance to redeem himself but make it clear what behaviour you do not want to see from him (comments on other peoples behaviour or abilities). If he 'misbehaves' just take him to the side and tell him that behaviour like this is exactly what you mean.

If he is unreasonable, you do not invite him for the next events. When asked why, tell him the truth. He makes the whole event a bad experience for multiple people.

He clearly has an understanding of what it means to be hurt by being excluded so you can use this to explain to him how he makes people feel.

Remember when I did not invite you to X? Well that's how [other person] feels when you say things like that about them.

Answer 2

AK_is_curious already gave a brilliant answer regarding handling your coworker.

However, I've got a hunch that this (as in so many cases here on IPS) mostly revolves around your own feelings and attitude. You want to make him behave politely without making him feel bad - because you're a nice and compassionate person. But the answer very likely is that it's just not possible to make him change his behaviour without giving him some negative feedback and feelings about it.

Let's face it:

• he basically drove home the point that he thought my boyfriend was stupid
• my boyfriend is seen as a mutual punching bag to bond over
• "I know, I'm a terrible person." and makes a big joke out of it
• will guilt trip me while making a joke about it

He acts like a dick on those occasions. But you still feel bad about confronting him about it. As long as he gets away with acting like a dick and feeling great about it, he won't change - and he'll continue to offend people. Sooner or later he needs some boundaries to help him become a better person.

I'm not saying you need to be the person to give him those boundaries - but if you feel compassionate, you may just as well do it. If you don't feel compassionate, it's also OK to just avoid him as far as possible in the future and just keep a professional work relationship.

"I would like to tell him he shouldn't make fun of someone I care about, and for him to take it seriously with no joking and guilt-tripping."

It sounds like your sentence comes with an asterisk: "*But without making him or me feel bad about it!" And my guess is: you just can't. He has to feel bad about it to some degree, because otherwise he won't have any incentive to change his behaviour. And you likely will feel bad about it, because you were taught it's not polite to point people's rudeness out to them or to be confronting in any way or to cut people out. But the latter part is the part you can change. You can "allow" yourself to set healthy boundaries and enforce them. You can realise and keep telling yourself that his own behaviour is the source of his problems. You can realise and keep telling yourself that your boyfriend deserves better than being used as a bonding device.

Setting boundaries is something you can get used to, and it gets easier with practice. AK_is_curious already answered how you could do it.

Good luck!

Answer 3

Your TLDR is very misleading.

You are describing, in essence, someone who is flirting with you and being hostile to your boyfriend. By being open to him you encourage this behavior (... spend social time at his house ..)

A marriage ring and 10 years of seniority does not make a person harmless! Respecting your boundaries and your friend does!

I would strongly think about limiting contact to that person to polite-professional. Don´t react to jokes or guilt-trips about that. He will eventually go away when he sees you are no longer interested in him.

Answer 4

(Read: coworker is harmless, married, and acts more like he's my age.)

I am glad you put that in there because I was not getting that from the rest of your post.

You describe a guy ten years older then you, becoming friendlier, letting you in on personal parts of his life and belittling your boyfriend. I am seeing a guy here that at best is having a midlife crisis, and at worse is hoping to replace your boyfriend for a weekend or two. Who knows.

Someone suggested that you exclude please next time, I would suggest exclude everything except a contemptuous "How Dare You?". Should take care of anymore snide remarks about your boyfriend and squash any embryonic fantasies he may or may not be indulging in.

Answer 5

If a person bullies you or someone you care about as a "joke", you ask them to stop (especially repeatedly), and they keep going, it was never a joke. It's just a more socially acceptable way for them to say how they actually feel. I don't believe that he thinks highly of your boyfriend. You should believe what he's saying to you point-blank, which is how he thinks your boyfriend is an idiot. Would you want to be nice to someone who thinks your boyfriend is an idiot, and what's more, tells you as much? Cold, professional, and polite is the way to go here. No more outside of work socializing.

Edit: I didn't realize that you hadn't already asked him to stop. Try some of the suggestions above, and if he doesn't stop or tries to keep deflecting, then I stand by what I said above.

Answer 6

I think that the best thing you can do is to be very clear on it. And I don't mean only in what you say, but also in how you say it, your tone of voice and body langauge.

I get the impression you dislike direct conflict and like to deflect/ evade conflict by joking around it or moving the focus to you instead of the conflict. While this is a good way to go about it when minor things happen, this is not how to solve a bigger issue like this.

Take him aside, perhaps with your boyfriend there as well, if you think that is helpful, and very clearly tell him that you do not like it or appreciate it when he talks badly about your boyfriend, or other friends/ coworkers.

Don't make it sound like you are angry at him (even if you are) or that you blame him, make it sound like it is something that you don't appreciate and that you would like to make him attentive on the matter. I assume he will apologize and promise to not do it anymore.

If he persists, then be more direct and less friendly. If that still persists, you will have to evaluate your friendship with him and whether or not you want to escalate it to HR.

Something else, which is more personal opinion. If what he does does not stem from him being on the spectrum, I think him to be an ill friend. I had a friend to do the same thing, but to strangers while shit talking about myself and another mutual friend. And it broke a 10 year friendship. We got past it but it is nowhere near what we had before all of that happened. I regret that the friendship devolved, but I do not regretting cutting him out for a while. While jokes and banter are part of any good friendship, Respect and care should take priority. Especially so if he knows he is your boyfriend. I bet your boyfriend feels all kinds of not happy with the situation.