Ok, so I met up with an old friend from high school a week ago. She's now 17 and I just turned 18 (in college).

I'm a direct guy, so immediately I start flirting with her. It's been 5 days since we met up, and we've chilled together 3 times and texted everyday. She doesn't not like it because I can tell when someone is annoyed. Every time I see her, I go for a kiss sometime near the end of the interaction.
The first time, we were cuddling and watching a movie. After, I asked her what she would do if I kissed her (I know. A horrible move.). She said she didn't know, so I went for it and got a cheek. Then I asked her if chasing her was going to lead anywhere. She said that she didn't not like me. I smiled and winked at her, which made her smile. Then I took her home.
She's always giddy when I text her. We talk a lot.
The next two encounters I went for a kiss as well. Each time she says that it would be weird because she doesn't know me well enough and she hasn't kissed a guy in a while. She does like me though. Anyone can tell if this was a movie and they were watching it. She just might be a little scared to try a relationship with me (She's kind of shy).
Well, I've realized today that I have oneitis. Extreme oneitis. It's pretty bad.
So tomorrow I'm going to get my ears pierced (I've always wanted to try ) and she's' coming with me. After, I'm going to grab her hand and hold both of her hands against the car (Gently but firm); I'm thinking about telling her this:
"Let’s talk.
You know, you’re an awesome, sexy chick. I’d love to see where we’d go, but I’ve never been one to chase. Don’t get me wrong, chasin you has been a fun ride, but the chase... It’s done. You know me well enough to decide whether you’re in or you’re out. You wanna try us out or you don’t."

(You can tell I have extreme oneitis because I've literally planned tomorrow out. How sad.)

It's not gonna be too serious, but I'm not gonna be my normal super funny guy when saying this.

What do you think? I either get rejected and break away from my oneitis, or I'm gonna get the girl.

You know, I normally hate ultimatums but this hardly seems like an ultimatum to be honest. An ultimatum would be "i don't want to be friends. either date me or let's go our separate ways." I don't get that vibe from your planned statement.

I always liked the straight-forward, go-for-it speech. It's congruent with my personality, and bluntness has reaped rewards for me. But that's me. So I'm not going to tell you to not do it, but I would make a few suggestions.

I wouldn't call her a "sexy chick." It's not that big of a deal, but this girl seems reluctant for physical interaction. She seems like the type to be unconsciously put off by your insinuation that the attraction is largely sex-based.

The whole thing seems confident but I would throw in something about it's obvious she likes you.

Do not say anything until you have dead eye contact. Sly smile.

"You are an amazing girl, and I like you a lot. And it's obvious you like me. Chasin you has been a fun ride, but the chase... *pause*...It’s done. Give me a shot."

Wait for a response. If she doesn't say anything in 3 seconds, slowly go for a gentle kiss on the lips. If she turns her cheeks or rejects you in any way, you gotta just smile, say "alright then," walk away, and FREEZE HER OUT. Don't text her, don't respond to her texts, don't talk about her to friends, nothing.

good luck

Dude, this is great advice, man. THanks.

The problem is that I can't freeze her out. Her little sister and my little sister are friends, and I have to take her to their house and stay there.

I am curious to know something though. What would freezing her out do?

Dude.

NEVER GIVE AN ULTIMATUM unless you can live with the answer you dont want.

Just back off. Stop texting so much. Stop being so needy.

She obviously doesnt wanna hurt your feelings.

Im not saying she wont ever want you but right now she definitely doesnt.

She just likes you as a friend. She likes the comfort but she doesnt wanna lead you on anymore than she already has.

If you wanna get her to like you, you just have to start backing off, give her space and knock the one-itis shit off.

When she does come back, you have to maintain composure until she gives in.

Right now you are DEFINITELY in the friend zone.