We present VLA HI spectral line imaging of 5 sources discovered by ALFALFA. These targets are drawn from a larger sample of systems that were not uniquely identified with optical counterparts during ALFALFA processing, and as such have unusually high HI mass to light ratios. These candidate Almost Dark objects fall into 4 categories: 1) objects with nearby HI neighbors that are likely of tidal origin; 2) objects that appear to be part of a system of multiple HI sources, but which may not be tidal in origin; 3) objects isolated from nearby ALFALFA HI detections, but located near a gas-poor early-type galaxy; 4) apparently isolated sources, with no object of coincident redshift within ~400 kpc. Roughly 75% of the 200 objects without identified counterparts in the $alpha$.40 database (Haynes et al. 2011) fall into category 1. This pilot sample contains the first five sources observed as part of a larger effort to characterize HI sources with no readily identifiable optical counterpart at single dish resolution. These objects span a range of HI mass [7.41 < log(M$_{rm HI}$) < 9.51] and HI mass to B-band luminosity ratios (3 < M$_{rm HI}$/L$_{rm B}$ < 9). We compare the HI total intensity and velocity fields to SDSS optical imaging and to archival GALEX UV imaging. Four of the sources with uncertain or no optical counterpart in the ALFALFA data are identified with low surface brightness optical counterparts in SDSS imaging when compared with VLA HI intensity maps, and appear to be galaxies with clear signs of ordered rotation. One source (AGC 208602) is likely tidal in nature. We find no dark galaxies in this limited sample. The present observations reveal complex sources with suppressed star formation, highlighting both the observational difficulties and the necessity of synthesis follow-up observations to understand these extreme objects. (abridged)
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