SOURCE: Singer Touch & Sew won't loop bobbin thread
I believe you have a broken gear. These are difficult to repair on your own.
SOURCE: how to thread the bobbin on a singer simple sewing machine
Drop-in bobbin: Note: thread must change direction when entering bobbin shuttle notch. Usually bobbin will turn counter-clockwise when threaded properly.
1. hold bobbin so that the tail of thread is facing to left.
2. drop bobbin into bobbin shuttle.
3. pull thread toward you.
4. guide thread into notch and pull to left so that slot engages thread.
5. pull thread diagonally across shuttle toward back of machine.
6. draw bobbin thread up through needle plate with threaded needle.
SOURCE: Singer 301a Bobbin troubles
I just had this problem, too - if you have the manual, check out page 15. If you have removed the throat plate, you need to make sure that the position finger on the bobbin case base enters a notch on the underside of the throat plate. Fixed my problem right away.
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