let me map this out real quick.

im 18, freshman in college, and want to go after this 16 year old girl that my family has known for like 10 years or something. she goes to the high school i went to for my freshman and sophomore year, and apparently is popular there. my brother is in her grade. when we were younger we would hang out on occasion but we never had a big conversation or got to know each other really well. shes not ditzy or dumb, she comes across somewhat quiet yet you can tell she has a more open side around people she is confortable with. unfortunately, the only way i can communicate with her right now is through facebook, but i dont know how to go about it, and she doesnt seem to be on very often so im thinking i may have to message her rather than chat with her. im not really looking for a pickup, ideally id like this to turn into a relationship. shes the kind of girl who i know if i dont do this i will have wished id at least tried something ten years dont the road. any tips or advice would be greatly appreciated, thanks.

ya facebook game can be tricky, i'm a senior in college so i know how it works. I do think sending a message would be the best thing to do... use some cocky/funny material, say something maybe that reminded you of her (cause "obviously" you wouldn't just message her randomly for a pick up/relationship right? wink wink)

maybe say something like
"omg check this out... I was walking to class today and there was this dorky looking girl in my class and she looked just like you!!!! it was crazy, too bad she ended up being [insert whatever here]."

after she messages you back tell her to come party at your college sometime, neg her by saying hopefully she can handle "big college parties" or something, get the digits, and start working some phone game.
hope this helped in some way!

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**~~Feed Her To The Sharks~~**

thanks. yea negging her on the basis of "seniority" seems like a good idea haha. one thing i forgot to add into the main description of this situation is that one of her best friends and i were a "thing" a couple years ago. although her friend moved away so i think they arent as close anymore, but she just moved back here recently

heres what i went with:

victoria I was walking to class yesterday and I saw this scrawny girl who looked literally just like you, if I hadnt known better I would have thought you were at (my college)... haha hows high school?

Scrawny is a way harsher neg than dorky. Watch out with negs when you talk about their physical appearance, women spend a lot of time and money trying to look their best.

Also I don't think you should be negging this girl as you already know her. Negs are used in initial interactions to show value in yourself and project an image that you're not intimidated as such. She knows you, so just be playfull and fun with this girl and then suggest you should hang out.