How can you (or he) lose anything? If you is synced the iPhone with iTunes (on computer), all of your apps and music (even for items purchased on iPhone) should be backed up in the computer's in the iTunes library. You can check your iTunes library now, by selecting the media types in the iTunes sidebar, under LIBRARY. If your apps and music appear there, you can re-sync them to your iPhone, even if lost or broke your iPhone and had to get a replacement.
Furthermore, any songs or apps purchased from the iTunes Store (on computer or iPhone) can be re-downloaded from the iTunes Store (as long as you use the same Apple ID used with the original purchase). From the main iTunes Store page, find Purchased under QUICK LINKS. On the Purchased screen, you can check for your previous purchases from the iTunes Store. If it's there, you can re-download it. So, even if you lost or broke your iPhone AND you lost or broke your computer, you can get those purchases from the iTunes Store back.
Your boyfriend should do the same thing and get back the stuff he lost previously (at least the items that were purchased from the iTunes Store).
FYI - The most current iOS version for an iPhone 3GS is 5.1.1. The upcoming iOS 6 should also be supported.
iOS 5: Updating your device to iOS 5
iOS: How to update your iPhone, iPad, or iPod touch
If you are currently running an iOS lower than 5.0, connect to your computer & click on the "Update your device using iTunes".
Tip - You may need to disable your firewall and anitvirus software temporarily. Then download and install the iOS update.