Help keep your middle schooler's spirits high with uplifting entertainment. Include a few books written by well-loved tween authors, such as Judy Blume, or some funny, lighthearted movies about school life. Buy a subscription to a tween magazine, but avoid ones with overly made-up or idealized models. Get her a gift card to an online music download service. Include a list of podcasts she may find interesting and can listen to on the bus journey.
Get your middle schooler off on the right foot nutritionally with a basket of healthful snacks. Include cups of yogurt, some granola, cereal, fruit and baked potato chips. Include a pamphlet on the importance of eating right and encourage him to pay attention to what he consumes. You could also buy him several gift cards to restaurants with healthful options, such as Subway, or give him a booklet of IOUs that promise to take him out for a healthful dinner once a month.
Help your middle schooler stay organized with a day planner that fits into his backpack. Fill a pencil box with various supplies, such as pens, paper clips, a mini stapler and hole-puncher. Include a flash drive for saving work at home or the school's computer lab. Give him a locker caddy for keeping spare supplies. Include a new alarm clock for getting up on time and a new gym bag for keeping track of extracurricular equipment organized.
Middle school can be socially very rough on some kids. Put a couple of DVDs or pamphlets in the gift basket explaining and preparing her for the possibility of bullying and peer pressure. She may blush, but you could also include a few tween-friendly advice books, such as "How to be popular" or "How to kiss." Include a booklet of gift certificates that entitle her to various social experiences, such as staying out one extra hour or hosting a slumber party at your home. Give her a cell phone (set strict rules about its use) so she can text her friends on the weekends.