First off, why does it look like you cut that out and scanned it into your computer lol?
Anyway, first you need to get your inner game handled. Through your post I can tell it screams, not confident, not in control, not at the center of your universe, not living in my own reality, letting other people really define my life, etc.
You need to change ALL of this before getting the image down. New mindsets, new paradigms, new techniques, new beliefs. Can't go through all of them now but here's a few:
All women want you. They do. Tell yourself this over and over, and you'll believe it.
I'm a catch. She's lucky to be spending time with you, because you are going to make sure she has a TON of fun when she's with you.
I'm a cause not an effect in this world. Don't let things happen to you, make things happen. You've already taken the first step into improving yourself, don't let anyone take you off your path. right now this is your path in life. You want to evolve and improve, LET NO ONE TAKE YOU OFF THAT PATH. Part of being a real man is knowing where you want to go and get to in life, and then doing it. I guarantee you if you surveyed 1,000 men, about 10-30 would actually know their path in life, and probably less actually will stick to it and persevere. PERSEVERE, CONSTANT VIGILANCE, do not be swayed off. When you are taken off your path, you become less of a man. A man is supposed to be a leader, he needs to know where he's going, and he needs to know how he's going to get it. Be THE man, you are surrounded by a bunch of beta males, don't treat them like crap (thats something someone who's insecure would do), but know that you need to be the dominant one, always ahead, all the time. Summer vacation is coming, this is the perfect time, I'm going to be improving myself too.
Theres so many more but I don't have time.
Then you work on outer game, appearance, technique etc. You should be doing them hand in hand, but you really need to get inner game handled first. I could give you the most incredible lines, plan out every scenario, give you everything thats been used to catch women like Angelina jolie and paris hiltion, and guarantee you, without your inner game handled, you'll be demolished.
Look up David DeAngelo
Look up Mystery (aka Erik Von markovik).
Find their products "somewhere" (I'm sure you have more than one way of acquiring e books on the internet at a VERY low cost

)
And you aren't that bad. Work on losing some of that weight, toning some of it down, you don't have to be a muscle head, but at least try to get that shape and cut going for you, and as for your hair...hmmm. You look like a skater type of guy, but you've gotta do something with the hair, make it stand out.You tried getting it cut and gelling it back? How about making it straight and tying it back. I'm not the worlds greatest hairstylist so thats something you should get this women to handle.