So I'm 16 years old and I'm really shy. Sometimes I don't talk to strangers/people I'm not close to because I'm not comfortable/don't want to embarrass myself/nervous, but most of the time it's because I can't think of anything to say. Nothing comes to mind! How can I work on this?! I feel so bad sometimes because people will be telling me stories or trying to get to know me and all I can say back are things like "that's cool". It's not that I don't want to make friends, it's just that I can't. I get jealous of my best friend all the time because she's so outgoing and it's super easy for her to make new friends.

And on top of that, I have a compulsive eating disorder so I'm super self-concious and have a really low self-esteem.

You can turn being shy of what you think is a flaw into an asset by considering yourself a good listener. Find a common ground between you and the person that you are conversing with and expand on that, such as your thoughts on a book, a movie, etc. You don't have to lead a conversation in order to make friends, but it does help to contribute every once in a while, and usually with more than two syllables.
As for your compulsive eating disorder, is all this a contributing factor or did something else happen? If you can, please try to give more details.

Stop comparing yourself to others - I'm still in the process of overcoming my shyness. But some tips that have been helping me:
1. Stop caring so much about what you're going to say next and what to say. I realize that I get so caught up in thinking that I never end up saying anything at all.
2. Be yourself. Don't consider alcohol as a way of helping you open up.
3. Help yourself become more comfortable so you are not so insecure. Observe people and the surroundings.
4. Build up your confidence and become happy with yourself (be your own best friend).
5. Knowledge and intelligence.
6. Study people to help understand how people act.
Good luck and let me know how things go:)

There are a lot of shy people out there and yeah, it's a process. I agree with nicespringgirl but to add my own two cents. I was never particularly shy around strangers which is odd. I always have trouble maintaining friends that I want to have long term friendships with. Its one of those "making sure i don't say the wrong thing" things. And well. Like above said don't worry about what you say, just as long as your not lying. Personally, if I were you, I'd try to get a job where you work around people a lot. It might take a little while but you'll find yourself coming out of your shell more and more. Good Luck!

One good way to always have something to talk about is to ask the other person questions about themselves. Most people like to talk about themselves when asked. So just ask them a question about what they like to do or where they were born or even what their favorite color is and why... this will usually lead to more questions and more talking. Just pick something and ask away and then you'll probably think of things about you that are similar that you can talk about as well. Good luck!

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Originally Posted by folk_death

So I'm 16 years old and I'm really shy. Sometimes I don't talk to strangers/people I'm not close to because I'm not comfortable/don't want to embarrass myself/nervous, but most of the time it's because I can't think of anything to say. Nothing comes to mind! How can I work on this?! I feel so bad sometimes because people will be telling me stories or trying to get to know me and all I can say back are things like "that's cool". It's not that I don't want to make friends, it's just that I can't. I get jealous of my best friend all the time because she's so outgoing and it's super easy for her to make new friends.

And on top of that, I have a compulsive eating disorder so I'm super self-concious and have a really low self-esteem.

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Pick an ugly person to talk to and practice with them talking

Great advice above. Can't even think of anything to add except stop beating yourself up, you're only 16, it'll all come right in the next couple of years or so. Check out some good 'Build Your Self-Esteem' books.

I recommend -

Everyday Enlightenment - The Twelve Gateways To Human Potential by Dan Millman

Discover Your Worth

“No matter how intelligent, attractive, or talented you may be - to the degree you doubt your worthiness you tend to sabotage your efforts and undermine your relationships. Life is full of gifts and opportunities; you will open to receive and enjoy them to the degree that you begin to appreciate your innate worth, and to offer to yourself the same compassion and respect that you would give to others. Discovering your worth sets your spirit free.”