I'm sorry this is long! I tend to type a lot.
Since my fiance and I got engaged, I've been having a lot of issues with my bridal party selection.
Some of the problem stems from the fact that my fiance was pretty clear about wanting a smaller bridal/grooms party. He had picked out a best man and four groomsmen effectively the day we got engaged! (Kind of cute

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Limiting my bridal party to five people was difficult because I have a lot of very close friends from highschool, as well as friends from college. In addition, myself, and my family, really wanted to include my cousin.
I ended up selecting my best friend from highschool as my MOH (I'm an only child), and three of my closest college friends, as well as my cousin as bridesmaids. During college, my three friends and I were very close all four years of school and did everything together; we continued to be close after graduation, but lately in the past year some of us have drifted apart. Myself and one of them had an unspoken falling out for a while that really hurt me; we've since made up but things haven't been the same. I ended up asking all three of them to be in the party, as I felt like there was no way I could break up the group (I didn't want to hurt her feelings). I had suggested having one of them be a 'representative' for the group to one of them, but she informed me that the others would be extremely angry and hurt if i left them out. Long story short, I filled up my bridal party pretty quickly:
Yet later I realized that by doing this with my college friends, I ended up leaving one of my long-time highschool friends out. She's super dear to me, and although she has been supportive and hasn't said anything about not being in the wedding, I still feel terrible that she's not in it, especially when some of the other girls and I aren't as close anymore.
It's a few months later, and not having my HS friend in the wedding was really bothering me; So I mentioned it to fiance to see if he would bite on adding another member to our party, and he wasn't very receptive. Things are difficult for us right now as we just moved, he just started a new job, we are a little strapped for money, and I know he is worried that adding another person means adding another expense. He said that he thinks it will look weird to have an uneven amount of people in each party, and that having five people is already too big..plus there is the additonal cost of another dress, and possibly another groosmen..at the end of all of that he told me if it really means a lot ot me to do it, but I feel like I can't because I would feel guilty knowing it's not what he wants.
In the end I'm kind of a mess. I don't want to pressure him or stress him out, but I am feeling a little sad about leaving out my friend, and I"m not really sure if it's even that big of a deal. We still have over a year before our wedding, and fiance has said to mention it again after we're more settled; but I know how he feels about the goup size, and having to possibly add someone to his party isn't going to change.
Not really sure if I should let this one go, or pursue it further. :-/ I know we both have to compromise on what we want, and I don't know which things to push and which to let go. I think my friend will be fine not being in the bridal party, but I will still be sad that she isn't.
-May