Problems with Barels, Cones and Frizeebs

Is it me?  I'm trying to prgress my 22' and 45' on line work but am finding that the rope or line catches under or round the barrel, cone or frizbee - and I've tried all three - As it catches Nancy feels the pull and turns into me - giving to the rope beautifully, so she is doing exactly as I asked and I can't get a flowing figure of 8 because of this - what am I doing wrong?