Density functional theory (DFT) has been utilized to study the vinyl radical and fluorinated vinyl radical series, C2H3-F-n(n). n= 0-3. Six different functionals-B3LYP, B3P86, BHLYP, BLYP, BP86, and LSDA-were used. A double-zeta basis set, augmented with additional s- and p-type diffuse functions as well as additional polarization functions (DZP++), was employed for all of the computations. Extensive calibrative studies have demonstrated that the DZP++ B3LYP, BLYP, and BP86 methods do a good job in the prediction of electron affinities. Neutral-anion energy separations were used to calculate the adiabatic electron affinities (EA(ad)), the vertical electron affinities (EA(vert)), and the vertical detachment energies (VDE). These electron affinities were found to get progressively larger as the number of fluorines is increased; ZPVE-corrected values predicted by the reliable BLYP method are 0.66 eV (C2H) 1.54 eV (C2H2F), 1.96 eV (C2HF2), and 2.40 eV (C2F3). This trend can be attributed to increasing anion stability, which can be rationalized in terms of inductive and negative hyperconjugative effects. Optimized geometries for all of the neutral and anionic species, which are indicative of the aforementioned effects, are presented. The 1-fluorovinyl radical is found to lie lowest in energy of the mono-fluorinated species, whereas the most stable anion of the same stoichiometry is a fluoride(...)acetylene complex, which is found to lie 19.5 kcal mol(-1) lower than the 1-fluorovinyl anion using BLYP. The most stable configuration for the difluorinated species is 2,2-difluorovinyl for both the neutral radical and the anion.