Anonymous:
My friend, who I haven't seen in forever, is going to anime expo this year. I'm going in ott sweet and she's cosplaying but she told me last night one of the days she's going in lolita and posted the design she is making… It is so extremely Ita. I don't know what to do. I already mentioned that the skirt should go to the knees but thats not the only thing wrong with it. What should I do?

Rather than saying that it’s ita which will always come off as an insult and there’s really no way around it, tell her that it’s just not exactly Lolita. Point out the things that are wrong, explain the problems with them, and offer suggestions as to how she could improve on the issues. Explain to her that there are important elements that make something Lolita and if they’re not present it stops being Lolita and maybe use the cake example (You can substitute, add, and remove certain ingredients but if you take away important things like flour and eggs it just stops being cake.) If she decides she likes it the way it is and doesn’t want to change it then that’s up to her, but explain these things to her and request that she not say the outfit is Lolita. There’s no reason to say it’s Lolita when it clearly isn’t and if she’s not claiming that it is there’s not really any harm to be done.

I wish I was strong like you to say it when people are hurting me. To protect myself... I admire that in you... Just saying...

It’s just something that I’ve learned after years of being a doormat. Most of the time if someone is doing something or saying something to me and it’s obvious they’re just trying to get a reaction I just won’t give it to them. Other times I’ve found that something as simple as telling someone in a firm voice that they’re being rude and they need to stop is enough to get them to knock it off. The trick is to not stoop to their level. Point out to them that they’re being stupid whether it be blunt (“You’re being immature and you need stop”) or something with a snarky hint to it (“Where’s my sheep? Oh you’re so clever! I’ve never heard that before! Bravo!”) and leave it at that. 
It can be hard sometimes but if someone is hurting you it’s important to make it known to them and whether they were aware of it or not you should do what you can to get it to stop. 

Anonymous:
this isn't really a question but my friend keeps saying i cant be lolita because i wear glasses?? i know its not true but she always makes comments about how my glasses ruin my coords and how i should get contacts (i have astigmatism + i'm just squeamish about putting something in my eye..) or get lasik it's really getting to me do you have any advice on how to get her to stop?? she's been doing this for a couple of years now

To be honest I probably would have just snapped at her at this point. Just tell her to shut up and drop the subject. You’re happy with your glasses and you don’t want to have to deal with her crap anymore and you shouldn’t have to. She’s been saying it for years and you haven’t changed so what makes her think you’re going to now? Be blunt and straight forward with her about it.

Ah! Sorry, typo on the boyfriend one... It was my current boyfriend who said I would look beautiful in lolita, not my guyfriend... Thanks so much for the advice though! :) Also, what is the least I can expect to pay for a legitimate lolita dress?

Oh well if your boyfriend thinks you look beautiful your guy friend can go screw himself his opinion doesn’t matter one bit. You’re very welcome dear.
As for the least you can expect to pay, that depends a lot on what you’re looking for and what you want to buy, as well as any sizing needs if you would happen to need something custom or not. When you take into account the cost of shipping and things like that though, Bodyline is probably the cheapest legitimate place you can buy from and a dress from them will run around $40-$50.

Anonymous:
Hey! My guy friend tells me that if I wear lolita to school (I will be a freshman next year) then I will never get a boy friend, or my boyfriend will not want to be seen with me... I recently sent him a picture of what the style is and he thought I would look beautiful in it, but I am still a little bit worried... Also, any tips on making my nose look smaller?

It sounds like one of two things is going on. It’s possible that your friend is just trying to scare you out of getting close to any other boys because he wants you for himself. Like, he’s trying to pull this “All other guys are assholes and I’m the only guy who thinks you’re beautiful in Lolita and the only guy who ever will” crap. Or it’s also possible that your friend is a douchebag (actually if he’s trying to pull the crap from the first scenario he’s probably a bit of a douchebag either way.)
Whichever one it is though, forget him. There are plenty of Lolitas who have perfectly happy relationships. There are Lolitas with boyfriends and Lolitas with girlfriends and Lolitas who are married happily and have been for years. The idea that you’ll never get a boyfriend because you dress in a way that makes you happy is silly anyway because why would you want to date someone who is that shallow anyway?
As for your nose, there are things you can do with makeup but it will differ depending on what exactly you aren’t happy about. If you search “how to make your nose look smaller” on youtube though you’ll get a ton of results.

Anonymous:
Is it ok to bring a non-lolita friend to a meetup for support, or would it be weird to bring someone not dressed in lolita? I'm considering going to my first meetup soon, but I'm very shy and even if I tried meeting people online first I'd still be very scared and nervous.

I think it’s a very good idea but you should bring it up with your comm first. Usually they’ll say it’s perfectly fine but for some meetups, like if it’s a tea party and there are only a certain amount of seats reserved, they’ll want to save those spaces for people who are actually a part of the community. 

Anonymous:
good afternoon! can you give me some advice? I have super bad social anxiety. Do you think it's a bad idea to goto a lolita tea party? I have no idea what to expect. I really don't want to speak in front of everyone by myself or anything like that.

I don’t think it’s necessarily a bad idea to go, I think you should just really prepare yourself. Something I’ve done because I get very shy and nervous around new people is before going to a meetup I asked it if was okay to bring a friend along. Even if your friend isn’t a Lolita (which you should mention to the group) having someone there that you know and can easily talk openly to can help you feel more comfortable and serve as an icebreaker, especially if your friend is an outgoing person. Just make sure to clear it with the people hosting the meetup first because there may be limited space at the tea party and you want to make sure there is plenty of room for the people who are actually part of the community before you bring someone else with.
Another option would be to try to make friends with just one member of the community before going to a big meetup. Getting to know one person can be much less stressful than trying to get to know a whole bunch of people at once and having had previous contact with someone in the group will help you feel more comfortable at the meetup because you already know someone and they can help to introduce you to everyone and you won’t feel so alone.

Anonymous:
I've only ever told a few people outside of my family that I wear lolita. I don't know them that well, and I figured if they didn't like it id never have to see them again anyway, but everyone I wear it in front of loves it! I want to like announce it some way, but I don't know how. Should I start posting pictures on FB? Or maybe just wear it whenever I want and screw my friends opinions on it?

I would either start by posting picture on Facebook or wear it when you’re going to hang out with your friends but not in a public setting. Don’t make a big deal out of it because it shouldn’t be a huge deal. It’s just the way you like to dress. But I think to an extent you do need to respect your friends opinions on it. I’ve said this a lot before but I really need to stress how important it is. Some people are comfortable with getting attention and some people aren’t. If someone is out with you while you’re wearing Lolita they will be getting attention by association and while your friend might love your Lolita, they might not be comfortable getting that attention. If your friends opinions are more like “That’s stupid why are you wearing that?” then feel free to say screw them. But if they’re simply not comfortable with being with you while you’re wearing it that is something you should respect and see what you can work out with them.

Anonymous:
Hi! Um, this sounds kind of dumb but I have this friend who usually wears sweet lolita and I'm trying to get into lolita, but she keeps forcing me to go for a gothic style. I have no problem with gothic (it's very gorgeous), although I'd really prefer to wear sweet and classic. I'm afraid she'll think I'm trying to "be like her" in a way. ;;

That’s silly. You should wear whichever style you want to wear. Just tell her “I like Gothic but I don’t want to wear it as much as I want to wear Sweet and Classic so please stop trying to force me into Gothic.” And if she claims that you’re trying to be like her just tell her that she’s being dumb and that you just like those styles better. You can wear whatever styles appeal to you and she has no right to tell you not to. She is your friend, not your boss.

Anonymous:
To the friend-making-a-big-deal-about-skirts anon: I had a similar situation with an acquaintance in high school. Every time I wore something frilly, feminine, etc. (not even Lolita) he'd flip out. And not even in a negative way. Like, creepy overly praising, and he'd keep referring to me as "Misa" (from Death Note)... Sometimes the best thing to do is tell them it makes you uncomfortable. Be brutally honest with them. If they can't take it, then they weren't meant to be your friend anyways.

If I were in that situation I probably would have punched him for calling me Misa. I’ve always hated her as a character.
You’re definitely right. Don’t dodge the subject, be completely honest, and let them know how the situation makes you feel.