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I've been married twice and just kind of worked it out on how many I'd have. First wedding: My 3 best friends from childhood, my best friend from college(MOH... also my sister-daughter), my closest cousin and my groom's sister. We had 350 guests so I guess it did fit that ratio, but it wasn't intentional. This is really awful, but I can't, for the life of me, remember who all the guys were in the bridal party for the first wedding. I remember we had my brother, his brother, and his best friend (who was our best man) but I can't remember the rest.
Second wedding: best friend from college again (MOH), new very close who I'd become friends with at work during my first marriage, my groom's best friend's wife (so they could stand up together.. plus, I really liked her a lot.. still do in fact!) Oh, we also had 2 junior bridesmaids and 2 junior ushers who were all his nieces and nephews. It was definitely "his" wedding and "his" bridal party. The friend from work that stood up for me was with me when I met him. He had his best friend as his best man, one other childhood friend and his best friend from college (whose wife stood up with him). One of his best friends from childhood did the catering for us and gave us a very very good deal (pretty much his cost) and another of his childhood friends was a DJ and did the wedding as his gift to us.
I was pretty much having the second wedding because my second husband hadn't been married before and really really really wanted a wedding after being in all his friends' weddings. It was less expensive, less formal and much smaller. I only had my immediate family and closest friends there.. and a few "newer" friends who hadn't been around the first time I got married. I had two tables of guests (about 24 people). He had about 120 people there. I had a long talk with the gal who had been my MOH the first time about doing it again and offered to pay for her dress the second time, but she declined the offer. And, I have to say, it is a rare friend who is your MOH twice! She's still my closest friend.
Both times, the only expense I paid was giving them their jewelry. That was tradition around here and ensured that they all matched perfectly. I didn't choose outrageously priced dresses either, but the new tradition of dictating the color but allowing the bridesmaids to get what they look good in (and can afford) is a good one, I think.
I think you should just balance who you really want to have and who he wants to have for his half of the bridal party. Hopefully, you're close enough to the bridesmaids that if it's going to be a financial hardship for one of them and they aren't going to stand up only because of that, then you could help that one out if you can afford it. If you aren't close enough to openly discuss that, then they probably shouldn't be in your wedding party!
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