Conversations?!

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I've known this girl for a few years, we've had a few classes together in middle school and high school. She's started a few short conversations with me over the past year. As much as I'd like to continue the conversations, I'm generally too nervous to say anything really meaningful! I can't tell if she was really interested in me or just making innocuous conversation - I remember once she asked me about a game I was playing and another time she said she liked my glasses.

Well, we've ended up seeing each other more this year because of schedule changes for second semester, and this afternoon she talked to me for the first time in months. I was walking to a club after school and we ended up walking next to each other in the hall. We spoke very briefly. She said "What's up?" and I tried to reciprocate (but sounded weird - like "What's up for you?" ) She asked me what I was doing before she had to leave for wrestling practice, then we said goodbye. It was probably the most successful conversation I've had with her since middle school.

I'd like to return the favor by trying to start a conversation with her, but I'm not sure how I should do it. I see her briefly in gym and we share the same lunch period, so that helps, but I often see her with a bunch of people. And if I do try to talk to her...what do I talk about? I'm nervous.

That's a good question. A mystery to me too, starting conversations.

try getting her to laugh at herself. Say, 'will you wear a plaid wrestling uniform for for St. Patrick's Day?'; or, 'will the wrestling team wear red uni's for Valentine's Day?'; or, 'does that thing come in leather?'.

or try a joke - 'why does the Tampa Bay football team wear helmets? -- to cover their buccaneers'.

you can always wave, smile, etc. Can't hurt. I dunno...ain't got much to go on here, but 'hi' is always a good place to start...

Do you know of any of her hobbies? Maybe you could ask her a question about one of them. This is always good because then the other person talks about their hobbies, all you have to do is listen. If I am stuck for conversation, this is what I do and generally, it's successful.
If she asks you "whats up?"...maybe you could tell her in brief detail [less than 20 words] what you will be doing later on in the day. Generally, people don't want details, they just want a chance to be with you. This is something i've learn't after people have became annoyed at me when I responded with a 5 minute description on what I was reading/doing/researching etc.
I hope i've helped...let us know how it all goes.

Don't overthink it. The best thing you can ask anyone is something along the lines of "How did things go at X" (where X is something like wrestling practice, or a class you know she takes)

This question gives her an opportunity to give more than a one word answer, and should provide enough info for some intelligent follow up questions. It gets her talking about something she's interested in (people like that) and it shows your interest as well. Don't ask questions that can be answered in one word, because if you have trouble maintaining a conversation, that may be the end of it. By using strategic questions, you'll get her to do most of the conversational work, and you look good for it. A win-win scenario if ever there was one.

You know of her interest in wrestling, you can start there. If you share some classes, you can ask about a project in the class, opinions of a professor, or something. Pay a little attention, and you'll pick up on things she likes, and use them to begin the conversation. Just remember to ask open ended questions that allow for conversation.

BAD: "Do you like this class?" She might say "no", and then you have to work harder to develop a follow up, which is tough if you're an awkward conversationalist.

GOOD: "How is this class going to factor in your plans for after graduation?" She'll have to answer about what her future plans are, how the class is or isn't going to help, etc...you get tons of information to keep the conversation ball rolling.

Think of conversation like tennis. You want a good volley of back and forth, so say things that can be responded to, and ask questions that invite a response.

what do either of you like to do outside of school?

Today I really wanted to try to talk to her, and had plenty of chances to. I couldn't even bring myself to wave - I was so nervous I could barely move. I don't want to seem distant, because I like her, but I feel like something bad will happen if I do try.

Tell her that her makeup is (smeared,running,funny looking)*

*In a nice way