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I'm a member of the incoming class of 2013 so this is just my take as someone who just had the interviews this year.
1. No, because it is very outdated. Even worse it'll make it seem like you haven't done anything worth saying in high school.
2. I wouldn't mention it. It's a personal medical issue, not something to discuss with an alumni interviewer.
3. No, let the admissions officer worry about that. Your interviewer could care less, and it'll make you seem like your already setting yourself up for not getting in.
4. Definitely talk about your EC's.
5. I would definitely not talk about this. It makes it seem like going to Yale wouldn't really be all that important to you, among other things.
Also, as someone who was in a similar situation. At one point before we applied to schools my girlfriend and I talked about that. Trying to do that would've made a bad situation because if one person goes to a school that wasn't their top choice because of their significant other it gets in the way of the relationship because you'll come to regret it. Harder to think about, but just as importantly, if a couple breaks up there'll always be the regret of going to a school that wasn't his/her top choice. My advice, if you both have such a strong relationship it'll survive through college wherever you both go. and sometimes things work out great anyhow (they did for me). Of course, good luck whatever you decide to do.
6. Don't do it. It shows not only a lack of caring enough about the college process, but even worse a lack of interest in Yale. It would be like if someone you were interviewing for a job asked if you thought they would fit in at other jobs. Use your counselors, parents, friends, books, internet, etc for that.
7. Sure, wear it. Since you say it isn't really over the top it shoul dbe completely okay.
A final note. When talking with your interviewer talk about your EC's but also feel free to mention the things that really interest you even if they don't really show up in your EC's. It's finding something that you and your interviewer can just keep talking about for a while that makes an interview great, and sometimes it's your random interest that thye also share that gets that conversation flowing.GOod luck.
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