Awkward friendship situation - please advise

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Through my ex work, a small group of friends formed about four years ago. Over the years people have come and gone but the core group stayed the same about 6 of us.

We all had one thing in common which was that we had a dark sense of humour, do not get easily offended, and it is a safe space where anything goes. The group is very diverse on gender, race, sexuality etc. Some of the jokes would be deemed very offensive but just not to our group.

The problem has started that one of the core group members let's call Tom has gotten a girlfriend Ray. She seems lovely but when she joined us for a walk and dinner and conversation started it was clear she did not find our sense of humour funny. She was visibly uncomfortable. Nothing outrageous was said (I know how outrageous it can get) and all the humour was quickly nipped in the bud. We all hung out for four hours but it was largely awkward and quite serious. I had a one on one chat with her about her family, which was fine, but it felt like a workplace setting chat and was very different to usual. I put it down to her feeling overwhelmed at meeting her partners friends.

We all met up for a quick drink after work Tom and Ray included and and it was the same vibe, serious conversation about the Ukraine war. Half the group left soon after because they just aren't interested in talking about that in a social setting.

My friend Clara called me and told me what I was already thinking.

We don't want to be the people who don't include everyone. We would hate for anyone to feel unwelcome. Ray is a lovely person. On the other hand, this new dynamic doesn't work for us. The gatherings when she is there are no longer fun social gatherings, they're work place outings. If we were to be ourselves we risk offending Ray and effecting professional relationships (some people there work with Ray). Clara is Ray's direct supervisor.

Another person in the group Jax has a birthday coming up. They called me to help arrange something fun. The brought up that the dynamic changed when Ray was there and that maybe he should just invite Tom.

I'm not sure how to respond. I also don't find it fun when Ray is there but I don't want to upset anyone.

I get that when you have someone in the group who is shocked and upset, suddenly the jokes don't seem so funny any more. Tbh if Ray were nonbinary they'd probably give as good as they got.

Either you just get on with it and keep the jokes going or you don't. Probably they will both drift away naturally.

I don’t see anything wrong then. Although I wouldn’t like the explicit and vulgar stuff just because I get grossed out very easily.

Friends should be able to talk and not be afraid of being reported. That is actually scary if you think about it.

Yes we do feel scared in a way. There is nothing worse than feeling you may get cancelled for a joke.

We have such a diverse group- we tick just about every other box. But no-one is non binary or trans. Everyone gets joked about and the people who often find the offensive jokes the funniest are those who are being made fun of.

I can see why you don't want to just be yourselves when you can see you're making someone uncomfortable, you're not horrible people who don't give a damn. You can't live your life always pleasing other people though.

If Tom and Ray stay together, then either this friendship group collapses because most of you can't be your true selves around Ray or you start meeting up without Tom and Ray most of the time. I'd go with the latter. If they break up, you haven't lost touch with Tom and it goes back to how it was between you all. If they stay together maybe they'll have children and get too busy for many friends gatherings and the situation will sort itself out naturally that way.

Sounds as though Tom finds you entertaining and good company but he isn't really one of you, he doesn't think the same way so he's not joining in with the banter much, more of an observer. It's not real life for him, he's more reserved and polite and is able to relax with someone like Ray. Whereas the rest of you genuinely think like that, it's your personality and you make an effort to rein it in at work and in polite company.

It isn't feasible to invite only Tom if others partners are part of the group. He might be annoyed or hurt if he realises what's happening, but surely no more affected than if someone points it out to his face in advance that his girlfriend has changed the group dynamics and it's made the rest of you feel uncomfortable. If the friendship group collapses Tom loses you all anyway. No need for the rest of you to lose each other 🤷

Sounds like fun! But if Ray is a virtue-signaller who has all the fashionably correct opinions, those who work with her will not dare to express their views. That will kill conversation.

Especially on transgenderism, as people have lost their jobs for refusing to say they believe transwomen are women. (I know the law now accepts people’s right to believe that humans cannot change sex, but feminists have still been hounded out of their jobs.)

It’s a tricky one. Clara is most at risk, I think, as Ray’s supervisor. She would be foolish to let her guard down in front of Ray. Maybe see if Tom and Ray drop out by themselves?

I hope this works out for you and the group.

Sorry, cross-posted!

Ray is a lovely person. On the other hand, this new dynamic doesn't work for us. The gatherings when she is there are no longer fun social gatherings, they're work place outings. If we were to be ourselves we risk offending Ray and effecting professional relationships (some people there work with Ray). Clara is Ray's direct supervisor.

Another person in the group Jax has a birthday coming up. They called me to help arrange something fun. The brought up that the dynamic changed when Ray was there and that maybe he should just invite Tom.

I think someone needs to convey all of this to Tom. You risk losing Tom as a member of your social group, I suppose. But it's hardly relaxing to be on your best behaviour when socialising.

Talk to Tom. Explain that you like Ray but you're all censoring yourselves to accommodate her. Then change the subject. He might steer her away a bit more.

This.

Ask Tom if Ray is uncomfortable with how you all joke. Maybe she just needs time to get used to it. I mean she keeps coming, so it can't be that awful for her. Could it be more that something about her manner is making you feel uncomfortable, but she's actually fine?

I've been in your shoes op. Great bunch of work friends, had a real laugh except when two particular colleagues joined us.. these two only wanted to talk about work and related serious issues. When they didn't come, we had a blast. Unfortunately I can't recommend anything except maybe sometimes organise your outings for times when you know this couple is busy, and other times, invite them but be yourselves around them. If Ray doesn't like it she can stop coming

Maybe you all need to practise being fun, and funny, in a variety of settings including those where you can't be offensive. It'll be a useful life skill.

You seem really immature, esp your comment re people leaving because the conversation turned to the war in Ukraine, I csn understand why she doesn't like being around your group

I'm guessing you're talking about the kinds of joke to be found in the game 'cards against humanity'? Very inappropriate and un-PC but very funny to some whilst offensive to others. It's definitely a game I enjoy with certain friends but wouldn't even think of playing around others. I'd gently talk to Tom and find out what he thinks about the situation.

Maybe she's not offended, maybe she's bored?

If you’re all so cool and hilarious, I am not sure why you are spending so much time wondering about the thoughts of a random new girlfriend unless you are truly deserving of some calling out? You either think what you’re saying is okay, or not.

I wonder if Tom who has been single forever, will slowly disengage from your group, to do more 'couple things'. Ultimately you (as a group) don't trust her and haven't gained her trust.
Until then, I would ask Tom if Ray is ok with the sense of humour. You could explain that you are concerned she will take offence/repeat some of what you are saying out of context and and you are all a bit uncertain as she reports to Clara. I think he will understand.
I would not want to go to the pub and spend the evening discussing the war either.

@flyingant yes the cards against humanities humour.

From what I know Tom and Ray are really keen to hang out with us again. The humour was nipped in the bud so quickly that I really don't think Ray knows what sorts of conversations usually happen. From what I know of the others they don't really want to give it another try because they don't feel comfortable to be themselves especially Clara. Theres too much on the line if someone is offended.

I spoke to Tom. I feel bad. We met up for the birthday without Ray. I bought it up causally by asking Tom what sort of sense of humour Ray had and he got very defensive quickly. This would be the first Tom would know anything is amiss. I asked if she would find our sense of humour funny because it can be quite offensive.

Tom tried to reiterate that Ray wasn't offended the last time we met up. But this was because none of us said anything offensive because she was there. I told him that I went quiet because I was worried about offending her.

I also know she is sensitive about race. The second point I bought up is that there is someone in the group who is Indian and loves make jokes about his own culture. Many of the others also direct jokes and his expense to him and he finds it hilarious but it maybe shocking to Ray. (I truly understand this isn't everyones cup of tea). Tom said Ray is particularly sensitive to jokes about race. I said that is all the jokes that Pardeep makes then. Tom went quiet.

Tom said that if Ray was uncomfortable then she wouldn't call us out so it's fine. I said that no-one will say anything if she's uncomfortable.

It went quiet so I ended the very short conversation by saying that we would need to ease Ray in and could he please let her know about the sorts of jokes that get made so she can decide whether this is something she is uncomfortable with.

The ball is now in his court.

I'm wondering whether Tom is beginning to find the group sense of humour somewhat less funny than he used to.

last night he was laughing hysterically. After what people assumed about Tom I was watching closer to see if he found the jokes funny and he did. I had this conversation with him at the end of the night. He still hugged me goodbye.

So you all get together and tell hilarious close to the bone jokes all night?

Sounds a right old laugh.

I can't stand this kind of in group "banter" you get with these kind of intense friendship groups. If I was the girlfriend I'd not want to be hanging round with you all, but then I'm not a fan of friendship groups anyway and prefer to have friends I see on an individual basis. I used to be part of such a group at university, except I wasn't really, they looked down their snooty noses at me and saw the same thing happen to 2 lovely women who became girlfriends of male group members, they were basically bullied and hounded out by the toxic females in the group. Weird and very immature.

it's really not for everyone but when you have a group of people together that appreciate it its really refreshing to be in such a safe space where expression and freedom of speech is welcome. We have welcomed lots of partners and new colleagues to come and join us, we have just never been in a situation where the group dynamic has made someone uncomfortable. I'm not sure if I did the right thing approaching Tom as I didn't expect him to be so defensive off the bat