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Stop changing your date to accommodate others! It's your wedding...if the date works for you and your FI, then it will work for everyone else. We got married over Labor Day and invited close to 400 people. Over 300 still came, and who couldn't be there, we totally understood. It's over a holiday weekend...people are going ot have longstanding plans. As long as you're ok with that...I say stick with it.
@Anriya: I agree with @2PeasinaPod:
If you are inviting that many people, you will likely have some that can't make it, but many who will. It will be okay.
You will be surprised at how flexible people can actually be. You can't satisfy everyone as not everyone will be able to make it, no matter what you do. Stick to the date you really want, don't compromise for others or there will never be a right day to do it on! :)
You know...there are always going to be something going on around your wedding time. I say, if your immediate family is available that weekend, book it! Not worth the stress it is causing you now.
We went to a Labor Day weekend wedding recently too. Which works well for a lot of people since it's a long weekend. But if you plan on doing a long weekend wedding, make sure to let people know early so they can book cheaper flight ticket :)
We were pretty firm on our date, or at least month. So we just gave everyone notice far in advance and let others work around our schedule. If they can't make it, sorry then. it's our day and I want to do it my way. As soon I confirmed all my immediate family will be okay with the date, we just ran with it.
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I have had to change my wedding date so many times now that it's not even funny. I had to change it from June to August because it was too close to Hodag Country Festival for my FI. Then I had to change it from the date I chose in August because it was too close to the local fairs and it was on a weekend my mom's friend was getting married. Finally, we settled on August 18th. I became very comfortable with this date and liked that we didn't have any major holidays or birthdays around it. However, we just found out we are now expecting a baby.
Our options were either to keep the date and have me huge and 8 months pregnant at the wedding and not be able to fit into my gown, get married at the courthouse and have another wedding after the baby, or bump up the date. After a great deal of going back and forth, we decided to bump up the date so I could have my dress and because in the end we probably wouldn't have another wedding after the baby anyway.
We chose May 19th as our new date. The other night my FI went to the reception hall to book it for the changed date, but they were already booked and he picked the next weekend on the 26th instead. I'm not exactly happy about the date. May is already a busy month. My father's birthday, Mother's Day, my FI's birthday, and then our wedding too? It could have been worse, and it kind of happened that way too. I told my mom the date and she started fretting because it is close to graduation so there will be parties around that time people have to attend, and it is Memorial Day weekend which might hinder guests from being able to attend as well or go the other way and maybe make it more possible to come.
At this point I'm torn. Part of me just says heck with it. I'm so tired of trying to change this date and plan my wedding that I just don't care anymore. We have at least 300 guests to invite so there will still be a great deal of people there, so if some can't make it then that's just how it is. On the other hand, I would like it at a time that works for most. So I'm just stuck on what to do at this point.