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Character I am trying to create with the two object im using for boolean operations in lower portion

I am trying to cut two holed in this character using a boolean operation, since for some reason I had multiple issues filling and just extruding the complicated face with holes in it. You can see the two objects in the lower portion. They both have no doubles, and normals recalculated to the outside. The top one properly performs a difference operation, however the bottom one leaves a hole in the object

enter image description here

Apologies if this is simple, but I can't seem to find the answer by myself or in forums. Does it perhaps have to do with the lines visible on the top face in the lower portion? I guess a follow up question if this is a difficult fix, is there an easy way to fill faces between these two holes?

Thanks!

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In a case like this, you might be better off using the inherent mechanism Blender provides for filled 2D curves, which automatically makes a reasonable job of calculating 'Inside' and 'Outside'.

If you use a curve set to 2D, with a fill, in its Data tab > Shape panel..

enter image description here

Here, the curve has been given Solidify and Bevel modifiers directly. But for a more polished job, you might, for example, convert to a mesh, X > Limited Dissolve away the untidy triangulation, and I Inset the face-with-holes away from its boundaries, first.

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