When Gabby finds out she may be crushing on a guy in her class, she does what any hopeless love struck "tween" in the eighth grade does; tells her best friend, Lindsey. The girls come up with a plan, and not just any plan, to figure out how to ask him out, talk to him, and, in the end, try to figure out if he likes her! Lindsey is Gabby's wingman, or in this case, "Wing Girl..."