simple advice?

so i need help with a couple things goin on these days….

problemo numero uno- me and the youngin. hes a great guy….got everything i want in a guy just about but there are a few things going on in my mind a lot the past few days. for one he is quite a bit younger. i’m 20 years old and going out with a guy in high school…awkard i agree.  we were in high school together back in the day and thats how we met but it wasnt til after i graduated that i started to really talk to him and get to know him. now i’ve gone out with him before and this is the guy that cheated on me with my best friend angie…thought number two that keeps going on in my mind. i am almost 100% certain he will never cheat on me again but it still remains that he did and a lot of things he told me back then seemed to turn into a lie when he cheated and hes back to saying those same things again….its hard to believe it. another thing is i need to get real focused in school…i talked to the financial aid officer yesterday and today and she thinks i can get out by next march if not by december but thats by taking atleast 18 hours a quarter. i dont know if i have time to get into a relationship at this moment! last but not least…my friends want to enter me into this "HUNTSVILLE BACHELOR RADIO CONTEST thing." my all time favorite morning radio show has 3 djs and one is super hot and funny and the other two are going to do a "radio bachelor" thing to find him a girl friend. my friends think we would click but again im technically "in a relationship" plus all the other stuff….so heres the question….should i screw the age issue, get over the cheating past, and just see how things go or move on or stay single for a while? hes a really great guy and there really isnt any big problems…just age and past mistake….thats why im cautious to make a bad move.

number two-my hair. its time for a change….ive been blonde, brown, red, and for a while had some pink but now its time for something new…im only young once! haha. the following photo was photoshopped poorly to give a hint of what i’m thinking of….what do you guys think? should i go something like that or different? any suggestions?