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You did nothing wrong by scheduling the dress fitting on her birthday, but if it was traditional for you guys to celebrate her birthday together, you really should've planned this all better. Sure, she probably needs to get over it at this point, but you're not without fault on that one.
I'm gonna be honest - if I went to the trouble of throwing a shower for someone, I'd be kind of pissed if the guest of honor asked me how long it was going to take because she wanted to go take engagement pictures. However much you may have thanked her, she may feel like you treated this nice thing she was doing for you as an inconvenience. I'd be hurt too.
I also think you need to quit reading so much into texts. People often come off annoyed or upset over text when they really aren't - I myself had to explain to a friend recently that she was overanalyzing my text messages. She thought I was super upset over something when I was just a little frustrated and venting.
Yes, it can be tricky to stay friends with someone when you are at such different points in your lives. But you're not superior to Emily just because you and your FI have been together for so long and she has an on-off boyfriend. Maybe Emily's been acting weird because she's worried about how your marriage will change your friendship with her, or maybe she's picked up on your judging her love life (which it sounds like you do). You and Emily have been friends for a very long time, so if the wedding is causing that much tension, I think you need to put the wedding aside for a while and focus on the other things. There really shouldn't be that much you need to talk about regarding the wedding at this point anyway.
She can do something about all this and is choosing not to. There's no helping someone like that. If she is unwilling to make the effort to improve things, why should you put any effort into it for her? It's one thing to be picky about your next job when you are working and in a stable situation, but when you are unemployed and facing homelessness, you have to stop thinking of certain things as "beneath" you.
As harsh as it may seem that her family isn't providing much help, they may have been through her being entitled and unrealistic about things before and just can't deal with it again. If you want to offer some advice or moral support from afar, that's fine, but really, anything else is just enabling her and allowing her to take advantage of you (which she will).
OK, a few things here from an overthinker who managed not to overthink her wedding too much:
- There is no such thing as a perfect wedding day. There will always be something that doesn't go as planned or that you wish you'd done differently. Accept that now.
- The small details you are obsessing over are just about never what makes a wedding memorable. People mostly remember good food and drink and whether they had fun (was the DJ good, did people dance, did they like the people they were sitting with, etc.). Put more of your focus on that and not on the little details. Nobody is going to remember your exact flowers, and no matter how much you obsess over favors, chances are they'll still end up in a drawer somewhere.
- Wedding planning tends to be a long process nowadays, and you need to keep living your life during that time. Wishing you could quit your job to plan your wedding is not healthy. If I'm being honest, I didn't have anywhere close to this level of focus on my own wedding until 2-3 months out, and even then it wasn't like what you are talking about.
- If you can't step back from wedding planning entirely at this point, allow yourself a certain amount of time each day to focus on it, then stop when that time is up and move on to other things. You can increase that amount of time when the wedding is closer, but even then, it should never take over your entire day, especially when you are working. If you're just about the wedding all day every day for the next 8 months, you will drive yourself and everyone around you crazy. Lots of people love weddings, but nobody loves them that much.
Go for the red dress. It's gorgeous, and you'll feel fabulous in it.
Sides do not have to be even. Do not replace this bridesman. Wedding party members are people, not job positions that need to be filled. It doesn't say much about your friendship with either of these people that you think it's fine to just replace one with the other.