For 2,6-difluorotoluene (2,6-DFT), we determine the 6-fold potential for internal methyl rotation in the first excited singlet state S-1 and the cation ground state D-0 The sample is cooled internally by expansion in Ar from a pulsed nozzle. The S-1 - S-0 absorption spectrum recorded by resonant two-photon ionization (R2PI) yields the effective rotational constant F’ = 5.1 +/- 0.1 cm(-1) and the potential parameter V-6’ = -10.5 +/- 2.0 cm(-1) (staggered minimum) in S-1. We find dear evidence of potential energy coupling in S-1 between torsion cm and a low frequency out-of-plane bending mode b of a(2) " symmetry under G(12). In S-1 the unperturbed bending fundamental lies at only 78 cm-1; the magnitude of the torsion-bend coupling matrix element between the zeroth-order pure rotor state m(4) and the combination b(1)m(1) is 7 cm(-1). Threshold photoionization spectra detected by pulsed field ionization (PFI) through a number of S-1 intermediate states corroborate the S-1-S-0 assignments and yield the rotor constants F+ = 5.2 +/- 0.1 cm(-1) and V-6(+) = + 15 +/- 2.0 cm(-1) (eclipsed minimum) in the ground state cation Do. The adiabatic ionization energy is 73 674 +/- 5 cm(-1). We also present ab initio calculations indicating that for both 2,6-difluorotoluene (S-0) and 2,6-dichlorotoluene (S-0), the preferred conformation is eclipsed, which is unusual in S-0. The calculated vibrationally adiabatic torsional potential parameter V-6 " is + 14 cm(-1) in 2,6-difluorotoluene and + 52 cm(-1) in 2,6-dichlorotoluene, In other words the calculated energetic preference for the eclipsed geometry increases from the difluoro to the dichloro species. At the same time, the optimized geometries vs rotor angle or show increasing in-plane methyl and halogen wagging from the difluoro to the dichloro species, consistent with stronger in-plane steric repulsion. This apparent paradox in the vibrationally adiabatic torsional potential can be explained by a simple model comprising free rotation coupled by the potential energy to in-plane and out-of-plane bending vibrations, with the in-plane coupling stronger.