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A few months back, four of my friends and I started meeting monthly for Dungeons and Dragons sessions. We weren't all close at the start of our campaign, but are now a tight-knit group. One member of our group (let's call her Jill) asked if her boyfriend (Let's say he is Jack) could join at the end of the first campaign. I didn't have any issue with this since I didn't know Jack and the more the merrier. I have since come to find out that no one else in our DnD group likes Jack. They find him arrogant and annoying. We were all asked by Jill if he could join, but no one spoke up at the time. Now we are trying to figure out how to uninvite the guy.

Some of the dynamics at play: We all like Jill as a member of our group, but nobody would be terribly upset if she stopped attending. We just want to maintain our friendship with her. Nobody cares about Jack's feelings, haha. Jill doesn't date around too much, but most of the friends seem to agree that Jack will not last. Jack wants to run his own game, but he also wants to be in ours. This seems like the easiest way out of this situation: Somehow get Jill to be in Jack's game and continue our monthly game without them both.

While I believe that plan is the path forward, I am having trouble imagining the conversations that would lead to the desired result. Help me come up with some ways to navigate those conversations or any other useful solutions.

Updates: To clarify, Jack has not yet joined our group. The negative opinion of him has formed from other interactions.

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    Note that Role-playing Games SE is more used to handling questions in this setting and this would fit right in there if you don't find the answer you're looking for here. – scohe001 Sep 27 '18 at 1:50
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    To add to what @scohe001 said, check out this specific tag for more information: rpg.stackexchange.com/questions/tagged/problem-players – Maurycy Sep 27 '18 at 5:34
  • How aware is Jill of Jack's behaviour? Has she ever remarked on it? If you ideally want to keep Jill in the group, a factor in your approach would be how she reacts to the impression that the rest of you don't like Jack. – user8671 Sep 27 '18 at 7:07
  • @Maurycy I disagree, that is more how to fix problem players, the answer ends at "get them to leave" – WendyG Sep 27 '18 at 11:39
  • I'm not clear on something-- has Jack been playing with your group, or have they formed this opinion of him through some other interactions? – Upper_Case-Stop Harming Monica Sep 28 '18 at 0:26
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The base advice you would also get on Role-playing Games SE is:

Communication and honesty

This does not mean you sit in the game round and tell Jack he is arrogant and annoying. Jack is new to the group and has been introduced by Jill. You need to talk to Jill about this. Not only is she the only one who wanted him in the group, but she is also the only one who cares if his feelings are hurt.

You need to talk to her - as a group, not just you as the gm - outside of the game. Tell her that the entire group does not like how the dynamic changed since Jack got introduced. Assure her that you would still like her to attend, but that Jack is not compatible with the group. Refrain from using insults or complaining, but do bring examples in which Jack disturbs the group dynamic.
You don't have to judge Jack, but talk about his behaviour as difficult for the group.

Find a solution with Jill. Make the suggestion that since he wanted his own group anyway, he still has a group with Jill. Try to suggest that it might be best if he left the group, but do not give her the feeling that he is just being kicked out and she has no say in it.

It might not be a fun conversation, but if this keeps going your group will disperse. One person incompatible can easily ruin the fun for all players in the long run and no one will be in the mood to play anymore.

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The easiest, lowest-conflict approach?

Give Jack a shot.

I'm not saying that your friends' opinions of Jack are wrong-- they may well be 100% correct. But your current trajectory is to exclude him based on word-of-mouth from situations totally distinct from roleplaying, and you're set to cut Jill loose from your allegedly tight-knit group for essentially no reason at all. That's a pretty strong reaction in a low-stakes situation because you vaguely assume that you can't possibly have fun with him around. And as no one in your group saw fit to do more than silently allow Jill's request to be granted he may not be so bad that you can't endure him for a couple of hours.

If he joins your group for a session or two, and he's not a good fit (as sounds likely), then you have an actual reason to disinvite him, and your group can discuss it (possibly with Jill included). RPG.SE has plenty of information on handling that sort of thing. If Jack and Jill break up along the way, then the problem really solves itself. Letting Jack join isn't a permanent decision.

A key element of this approach is that you and your group should give Jack an honest chance. No badgering, no going from annoyance-level 0 to annoyance-level 9000 the first time he does something you don't like. You, as the DM, can also do a lot to distract, channel, or otherwise smooth over any tendencies Jack might have that the group finds disruptive. Another part of the DM's role is to help manage group dynamics (it's your table), but you have more options than kicking people out. And if it honestly doesn't work out, or the group just thinks the game is more fun without him, you can get there equally well at that point as you can today.

I strongly suspect that the reason you're having trouble imagining conversations that end with Jack excluded (and maybe Jill too) is that you don't have much of an affirmative reason to pursue that goal at this time. That's especially the case for you, as you have zero firsthand knowledge of him, which makes you a poor choice to spearhead the effort if you decide to ban Jack before he gets anywhere near your table.

If you do decide to uninvite Jack, before or after playing with him, it should be a group decision and discussed and conveyed outside of the game itself. The rationale you give should be truthful, but focus on the game itself and how he and the rest of the group don't mesh well with a result of a worse game for everyone. It's not about him (even if it really is), it's about the game that the whole group shares.

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    RPG Stack also has loads of references to 'Session Zero' where everyone has a chance to figure out exactly what they're looking to get out of the game. OP doesn't need this for their own group, but can always do something similar to see if Jack would fit into your group's playstyle. – Red Mage Jun 3 at 12:07
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Talk to Jill, not to Jack. Come as one.

You mentioned that Jack is not going to last, he isn't your friend, and that nobody cares about his feeling. Just to make it clear : don't talk to Jack about the situation. There is no need to make an uncomfortable situation out of this.

You need to talk to Jill, and you need to come as one. She has to know that it's not just you, but the whole group who can't handle Jack's behaviour any more.

We have been talking with the group and...

This is really important because it shows that you guys all agree on it, so you are not being a princess, and more importantly, it shows you care about her feelings: you had the thoughtfulness to speak with your other friends before won't hurt her.

Be gentle, but be direct.

You don't get along because he is an idiot. She doesn't need to know that Jack is an idiot, just that you don't get along. Do not spit on Jack behind his back, your friend Jill doesn't need that. You guys have more fun when Jack is away, that's all. Worst case scenario is that she takes it personnally and leaves the group, but imho, she already knows you don't like him.

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