This Time Around is a made-for-television movie starring Carly Pope, Sara Rue and Brian Austin Green.
In 8th grade, Melissa Rochester is a shy, geeky girl who has a huge crush on Drew Hesler, the most popular boy in her junior high school.
They decide to play a prank on Melissa and leave a note in her locker from Drew who tells her to come up to him at lunch and wait to be asked out.
She has since gained self-confidence, but still has trust issues due to her humiliation at school and refuses to maintain any long-term relationship.
The girls use a series of tactics to get Drew to ask Melissa out, and he eventually does, leading to a romantic date at his new restaurant (before it has officially been opened).