Bluetooth not working and Can't have "Repeat Playlist"

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I just noticed that I cannot connect my iPod touch 2G with my iMac desktop though both machines/devices are "discoverable." And for some reason, I dob't have "Repeat Playlist on my iPod Touch 2G though on my iMac the "Repeat Playlist" is highlighted.
Tried resetting this iPod touch several times but no success-all kinds of resetting. It's difficult to stop when you are running and music suddenly stops because there's no "repeat playlist."
Is there someone who has suggestions on what to do with this device?
Thanks so much.
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Replay

Regarding BT, the iPod Touch only supports headphones, keyboards, speakers, some game-to-game conductivity to different devices). You can transfer files. The BT profiles supported are here:
http://support.apple.com/kb/HT3647