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The pickup wheel under the bobbin stem may be worn and needing to be replaced (assuming it has not been knocked and bent off line) .
Try using a pen to push the bobbin stem further over when you are trying to wind it. If it starts to spin, then this is probably the answer.
That usually means the clutch or belt is worn out, and it's not worth fixing. You can buy an inexpensive bobbin winder for under $25.00 at WalMart online, and if you pick it up at a WalMart or FedEx facility like Kinkos, shipping is free. Does a better job anyway!
I think that you have had the wrong size bobbin. It should be a class 66. Look in your manual, it should tell you. If, that is not it, call Singer at 1-800-4singer and ask if it sounds like the timing and if so where can you take it to get fixed. This is a nice machine, my friend, has one and it is worth getting fixed if you like it.
Try adjusting the tension. It sounds like the bobbin thread is too loose or the bobbin is not in correctly. Try taking the bobbin out and turning it around and putting it back. When you hold the bobbin in the fingers of your left hand and you pull the thread out with your right hand the bobbin should be turning clockwise. If the nesting persists, try ajusting the tension one way and then the other to see which seems to help. Hope this helps!
Take out your bobbin case... there should be a small screw fixture on the side of the case...turn screw anti clockwise until you get the correct tension ... To test the bobbin thread tension...Remove the bobbin case keeping bobbin attached and hold it by suspending it by the thread...**** it once or twice, if the tension is correct the thread will unwind by about an inch or two. If it does not unwind at all...tension is too tight. If the tension is too loose it will drop too much. Goog Luck
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