Dear ESB: How do I tell my best friends they’re not invited to the wedding?

My fiance asked me to marry him a month ago, and I’ve been just floating on air ever since.

As we think about how we’re shaping our life together, we want the wedding to really reflect that, and to be more about the experiences we’ve had together and the joining of families than about extravagance or picture perfect details. We’re both super creative, and have tons of experience throwing events together (we own a business together and have probably thrown 100 big parties over the last 1.5 years), so we will get to all that stuff at some point, but we feel so lucky to have what we have and hold it so precious, that we have no interest in exploiting it or cheapening it with cutesy stuff, or throwing things in there just because. We want everything to be there for a reason.

With that in mind, we want every one of our guests to be there for a reason, and here’s where it’s getting reallllllly tricky, and why I’m writing to you.

First, there’s the size of the wedding. We’ve been leaning toward a quite small wedding – we’ve divided the list up into A, B, and C. The “A” list is only about 30 or 40 people, where the “B” list suddenly shoots us up to 100 at least, because of huge numbers of aunts and uncles and cousins that we barely know. We were thinking of doing a small ceremony and reception for only our “nearest and dearest,” and then heading to a club somewhere for some wild dancing with “B” and “C” invited along. I had real reservations about doing this at first, but I’m warming up to the idea. Thoughts?

But!! But, but!!! My real quandary is the definition of “nearest and dearest,” and compromise and when to make it. My fiance strongly dislikes one of my best friends from high school. Honestly, he dislikes my entire small group of friends from then. I have remained very close to them in my mind – we all live in the same city again and act, well, basically the way we did in high school. But honestly, none of us have much in common anymore, and we only actually see each other every two months or so. They’ve all been less than supportive as I’ve built this business with my now fiance, rarely attending events we put on. I could write a whole novel about this, and how hard it is to find other enterprising people who will allow you successes and celebrate your successes without feeling threatened themselves. Also, I frequently have whole conversations with them where they fail to ask me a single thing about myself. It’s all about them.

My fiance sees this and hates the way they treat me. I have had these thoughts, but never verbalized it, and hearing it from him is a big dose of the truth that I wasn’t quite ready to take. The friend he dislikes the most came to my birthday party recently and nearly ruined the day – he and his friends he brought along can be just foul-mouthed and disrespectful. I don’t want to risk that for my wedding, which happens only once and involves more than just me, and my fiance is basically saying that he doesn’t want to allow my less-than-thoughtful friend to attend our wedding at all. The thing is, until actually contemplating our very real upcoming wedding, I had basically assumed this group of friends of mine would be my wedding party. I always thought I was so lucky to have a group of old friends who I’ve know for 14 years, half of my life! But now looking at it, they’re not the people who support my life and seem to have my best interests at heart these days.

We’re almost thinking no wedding party, or the above-mentioned small ceremony followed by larger reception, which would relieve me of all of this to contemplate. But I can’t help but contemplate it all anyway. My fiance’s concerns take us beyond just the wedding and into life together, marriage together. He doesn’t want to have these foul-mouthed selfish people around our future children, around his gentle grandmother, and I completely understand and agree. Do I say something to my friend and explain why I’m not inviting him? Do I allow these friends to slowly phase out of my life as I phase into a new leg of my journey? I don’t want them to blame my fiance. I don’t want them to hate us, I hate to be hated. They assume that they are going to be a major part of this big life step for me, but even there I think they are doing it in a selfish way. The particularly-disliked-friend, mentioned above, said, when I told him of my engagement story, that he wishes that he was loved romantically as much as I am, and that he’s excited about more engagements because it’s pressure on his own boyfriend to marry him. I don’t want my wedding to be something that he uses to reflect on himself so much.

Thank you so much, any words of advice are SO appreciated!