But if she doesn’t get you the money by the deadline you set than go ahead and tell her sorry but you cannot share a room. Also, no charging privileges if room is in your name (your cc on reservation) and you won’t be together much in parks.
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This sort of situation is always tough. I like the deadlines and I think it’s fine to say that you are doing certain days solo (you are happy to give her pointers of course.). Better to be upfront about it all.
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Someone you haven’t seen in 20 years and you are thinking of sharing a 300 sq ft room for a week in an environment that sometimes pushes close family members almost to blows… AND she is showing considerable insecurities, financial and otherwise… Maybe I’m being a pessimist, but I foresee problems…
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I think you’re probably right @bswan26. I just sent her a very clear email about the money part of things. I’ll keep you all posted. Fingers crossed.
Yippee skippee!! I guess that was a lot of drama for very little trouble in the end. I wrote a carefully polite but very firm email with all your suggestions. I reiterated that it would only be about $100 more to use the Orbitz promo code I gave her to get a solo room. It worked! She’s currently on the phone with Orbitz booking her own room. Solo room for me!!! Happy dance. @ThatDisneyGuy_outer1 - will you find me a happy dance gif? I don’t know how to insert one of the fancy moving one.
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Wohoooooo that’s awesome. Enjoy your trip with old friends!
Glad to hear it worked out!
On my phone so not sure this will work but here goes nothing…
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Hahaha! I love Carlton. Thanks @ThatDisneyGuy_outer1. I promise not to tag you a million times tomorrow. @Sing_a_ma_jig_Keli might get jealous.
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No worries.
Stop threatening to tag my Disney husband. Don’t make me come out to NM, Sally!
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PHEW! As I was reading the beginning of this thread I was like OHHH THIS SOUNDS BAD! I am glad she is getting her own room! WAY better plan!
@ThatDisneyGuy_outer1 How did you get a gif to post?!!?!? I tried the other day and it didnt work!
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Funny you should ask… I just posted the instructions.
Just make sure you are linking directly to the gif file and it should work.
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Thanks!!
@SallyEpp_cot I am SOOO glad this whole situation worked out for you! I was sitting here reading your tale of woe and was getting increasingly more concerned for you 
Thankfully NHH decided to go the suggested route!! Yay! We need to have our WDW trips drama-less (is that a word? ha!) Can’t wait to read your trip report 
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Just read your story and I am thrilled she is getting her own room. Absolutely. Thanks for sharing because I have been in similar life situations trying to do the right thing and consider others etc etc etc. Happy for you.
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Thank you @whenuwish! I’m so lucky that the other 4 are all very compatible people.
We’ve started discussing strategies for splitting checks at TS restaurants now that we know that one of our number marches to the beat of a different drummer.
Does anyone have any suggestions for splitting checks? Will Disney TS restaurants to separate checks for parties of 6? I hope so. We will have to bring a calculator if they won’t.
@SallyEpp_cot I’m almost positive that I asked the server to do separate bills the last time we went with a group. I asked at the beginning of the meal and then reminded him at the end. Oh I hope I’m not steering you wrong.
Thanks @EthicalAddict! I hope that will be the case. Disney restaurants must deal with large parties all the time, so surely the will accommodate.
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You can def get separate bills. Glad this all worked out!