Wedding Date Clash

That's such a tough one. I don't think you can assume that your friend will cancel her plans if you pick the may date, so you need to think about that when making your choice. So it looks as if you can't have the venue you want, the date you want AND your friend being bridesmaid. I would suggest spending some time thinking through each option and imagining best and worst case scenarios before making a choice.

E.g. you might pick the May date and then have horrible weather - or have an unexpectedly good day weather-wise in November.

You might pick a different venue or date to accommodate your friend and then she gets flu the day before and can't come.

If you do decide to pick the May date, I would suggest ringing your friend to explain why - hopefully, she will understand that you can't pick a date that doesn't work well for you just so that she can come. You could still include her in pre-wedding events and also she might be able to join the ceremony online so that she can still be there virtually. I know it's not the same, but better than nothing.

Depends if your friend has already booked her holiday to some extent but the problem I see is finding a venue that will let you have your own caterers - this will drastically narrow down your venue options. so trying to tie a venue in with your friend is going to be tricky. I am nearby in Leicester and know a could of venues that allow outside caterers.

You might pick a different venue or date to accommodate your friend and then she gets flu the day before and can't come.