Select the Boyfriend Type Wisely
At the beginning of the game you will be required to choose a boyfriend type which helps set the goals for the "dream date." The three types are athlete, musician and skater. Your activities, clothes and popularity will determine whether you are successful in achieving your dream date and boyfriend in the game. For example, don't select an athlete if you do not want your character to go to sporting events. Part of the your requirements is meeting the needs of your boyfriend.
Keep the Parents and Best Friend Happy
In the game you cannot only look out for yourself and your boyfriend, you must also keep your parents and best friend happy. If your parents become upset, your character will not be able to leave the house. Your best friend can provide you lots of hints as you progress through the game. Go out for ice cream with her and share other activities, otherwise, when you need help, she might not be willing to do so.
Money
Money is needed to shop for new outfits and accessories that can help increase your "cool" levels in the game. Check with the school library for student jobs that are available. Look at the requirements and qualities required. The higher level of qualities you have in the game the higher certain jobs will pay you. If you are disparate for funds, go to a friend's house and walk the dog. Come back home and do any three tasks such as talk to your dad, listen to music, call your best friend or take a bath. After the three tasks are done, go out and wash the car and walk the dog. Repeat as many time as necessary to build funds.
Access
Certain areas are going to be off limits to your character. This can be as simple as watching what time it is on the game. For example, your character cannot go shopping in the middle of the night. Other areas require having certain "cool" levels. To get into these areas try on new clothes and accessories to enhance your cool. Remember to keep your dream date's needs in mind when dressing.