You need to get a relaxer put in your hair. You have a jew fro and you're always going to have a jew fro until you do this (regardless of if you are a jew or not). Relaxers are what black girls put in their hair to get it somewhat straight but it works WONDERS on white people hair and any stylist can do it, if you have previously highlighted or dyed your hair in the past few months they may be reluctant to do it because it can be quite damaging but you can typically find a stylist who is willing.
As for the style, if you want a longer look and are in your mid-twenties I think something similar to the following would be good...
<3 John Stamos.
Anyway...obviously you'll have to grow your hair out a bit more (but probably not that much considering you will add a LOT of length once it is straightened, you'll be surprised how much).
I would also consider going a few shades darker but you are going to have a hard time finding a stylist who will do this after a relaxer. You can accomplish it, however, with a SIMPLE and very easy on your hair dying technique (which I will explain later) and if you aren't sure you want to die it you can spray it with a natural color of colored hair spray while gelled to see how it would look.
I used to have NEON pink hair but needed to do a contest video for a Lifetime contest (which I was the national winner for! thank you $5 bottle of colored hair spray). Here is what it looked like with the spray on...
You could barely see the pink, and it washes right out...so it really does give you a good perspective of how your hair would look a different color.
Now...you can buy the colored hair spray I'm talking about at Sally Beauty Supply (I'm assuming you live in the states) for like $5 and it comes in blond brown and black..I think you would look MUCH better as a brunette.
If you decide you like the color, you can dye your hair VERY simply. All you need is (also from Sallys) a mixer (it's like a squirt bottle that you will mix all the ingredients in), 20 developer CREAM, and ONE box of the color of your choice. This will cost you less than $10, and make sure you get the CREAM and not the water/oil based developer or you will have a runny mess on your hands. Once at home, take the mixing bottle and add ALL of the dye (should be 1.5 oz if I remember correctly) 3 oz of 20 developer and 2 oz water, or until a runny but not INSANELY running consistency. What you will then do is squirt this all over your hair after it has been wet and shampooed (NO CONDITIONER) and rub it in like you're shampooing your hair, YES your hair should be wet while doing this! Leave this in for 10-15 minutes, rinse and use a deep condition on your hair for 5 minutes which is also available from Sally at the front counter for 99 cents. This is a tip I got from a stylist last time I was at Sallys and it gives me a very pretty blond color I am VERY happy with and is very easy to do maintenance on my hair while at the same time very little damage is done to my hair.
Okay, I know that was a lot, but I really like hair and have a lotttt of experience dying mine so if you need anymore help and I forget to check this thread, PM me.
One more thing, you NEEEED to get your eyebrows waxed. If you make it clear to the stylist that you still want very manly eyebrows she will accomplish this and you will be so happy with how much it opens up your eyes and NO ONE will even know you wax your eyebrows because she will make it look natural. After she waxes your eyebrows you can keep them up simply by plucking (you just pluck the hairs that are regrowing to keep the original shape she gave you!)
I hope this helps and I think if you made that change to your hair and shaped your eyebrows you will have NO problem picking up any girl!