My daughter just turned five and is painfully shy (when she wants to be). I am wary about character meets-she will hide behind my legs when she gets nervous, and honestly I wasn’t even going to push it. Then all of a sudden she has started talking about all the characters she wants to meet and what she is going to ask them. I have a feeling though once we get there she is going to be back to her shy self.
Any advice on how to best prepare her so she feels most comfortable? I won’t push her at all but I’m really nervous she will regret it after. For example, we went to see the Easter Bunny and she flat out refused but is now upset because we only have a picture of her baby sister and the bunny. Our ADRs are heavy on the character meals and I have heard that it feels a bit less pressure for those but for other characters that we have to wait in line I don’t want her to miss out.
Any ideas?
Well look there! Thank you so much!!
My then-DD4 was shy, too…afraid of costumed characters. A good way to ease her in is to have her meet either a character she loves, or a face character first. 
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Kennythepirate.com has tips for character interactions. They helped break the ice when my kids were shy of characters on our first trips.
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The kids I’ve traveled with may be shy at first, but usually warm up to the characters once they understand how the whole meet process works, at least, assuming the first couple encounters go well. To help those encounters go well, I (or another adult in the traveling party) will usually talk with the character, shake their hand, and show that whoever we’re meeting is really friendly and “safe”. That won’t work with every child and if it doesn’t, then I wouldn’t dwell on it, since making a big deal out of an encounter that didn’t go well may amplify the problem later.
Having something to break the ice, like an autograph book, also helps in some cases.
My daughter was quite shy the first time she met characters too. She ended up drawing a picture during breakfast at Chef Mickeys and was so proud of it that she would get up to show them. Once Donald made a fuss about her picture, she was in love.
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We recently took DS4 and DD2. The characters are pros and know how to handle timid children so I wouldn’t worry about it! My 4yo is typically very shy but he was the one running up to the characters and hugging them while my normally-daring and outgoing 2yo hid behind me!
My advice would be to watch youtube videos of characters interactions so your daughter can get an idea of what the characters are like. I think my kids were surprised that they were big, full-sized “people”. Haha!
My children were terrified of the characters when they were little and during our first trip. We made the mistake of doing a character dinner at Garden Grill our first night and it traumatized them. I would recommend starting with face characters - at a dinner or M & G. If she does okay with that, I would try seeing some other characters from a distance - waving at them during a parade is good. Then I would move on to meet and greets. My daughter felt more comfortable if we let her stay in her stroller and we wheeled her up to the characters - I think she felt safe in her umbrella stroller. Another option is to carry her if she isn’t too big. Hold her on your hip that is farthest from the character so you are between her and the character and see if she will give them a high five. If you can get her to at least do those things, then I would consider a character meal. It can be very intimidating when the big costumed characters bound up to the table. Giving her an autograph book to hand to the character is helpful too. Just ease her into it and she will probably come around.
It’s also ok to skip the character interactions if your child really doesn’t like them. Mine are happy to see the characters from a distance and spend their time doing attractions instead.
You did say she wants to meet some, so go for it! I’m just saying that if she doesn’t enjoy the first one, she might like to know that just spotting the characters can be a fun option. It can be like birdwatching. 
You could even make a list that she can check off when she spots them.
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