It is known that homotopy classes of free loops in a topological space are in bijection with conjugacy classes of the the spaces fundamental group, that every group is the fundamental group of some space, and that there exists an infinite (finitely generated!) group with exactly two conjugacy classes. This has the interesting consequence that there is some space with infinitely many distinct based loops but only two unbased loops (up to homotopy).
I'm wondering if there is any manifold that has this property. It is known that every compact manifold has finitely presented fundamental group (and that every finitely presented group is a fundamental group of a manifold), so showing there is a infinite finitely presented group with two conjugacy classes would suffice, although I believe this is unknown. But if we allow noncompact manifolds, perhaps things get easier.