I have suffered from various types of insomnia for what seems like my entire life. Either I can't fall asleep, or I fall asleep fine and wake up 47 times through the night, or I sleep fitfully. It is so hard on the body.
I have also taken so many types and brands of sleeping pills and to be honest they really only make things worse. I may sleep well on them, but I hate being dependant on medications, so when I stop taking them I withdraw, which means worse sleep. Some of them make it so you couldnt function if you were woken up (like Ambian CR). I really like Benedryl and it's safe to take. I even take it now. Two capsules an hour before bed.
Developing good sleep hygiene is important. A lot of people like to lay in bed and watch tv, read, or just hang out. Your body gets used to this and doesn't think of bed as a place to sleep, but a place to hang out. It is important to only use your bed as a place to sleep and have sex. Then when you lay down in your bed your body knows it's sleep time.
I assume your bf is young, but caffiene might be a huge culpret.
He's probably stressed from school/classes.
Not sleeping is such a pisser.