We study the behavior of eight diffuse interstellar bands (DIBs) in different interstellar environments, as characterized by the fraction of hydrogen in molecular form [$f$(H$_2$)], with comparisons to the corresponding behavior of various known atomic and molecular species. The equivalent widths of the five normal DIBs ($lambdalambda$5780.5, 5797.1, 6196.0, 6283.8, and 6613.6), normalized to $E(B-V)$, show a Lambda-shaped behavior: they increase at low $f$(H$_2$), peak at $f$(H$_2$) ~ 0.3, and then decrease. The similarly normalized column densities of Ca, Ca$^+$, Ti$^+$, and CH$^+$ also decline for $f$(H$_2$) > 0.3. In contrast, the normalized column densities of Na, K, CH, CN, and CO increase monotonically with $f$(H$_2$), and the trends exhibited by the three C$_2$ DIBs ($lambdalambda$4726.8, 4963.9, and 4984.8) lie between those two general behaviors. These trends with $f$(H$_2$) are accompanied by cosmic scatter, the dispersion at any given $f$(H$_2$) being significantly larger than the individual errors of measurement. The Lambda-shaped trends suggest the balance between creation and destruction of the DIB carriers differs dramatically between diffuse atomic and diffuse molecular clouds; additional processes besides ionization and shielding are needed to explain those observed trends. Except for several special cases, the highest $W$(5780)/$W$(5797) ratios, characterizing the so-called sigma-zeta effect, occur only at $f$(H$_2$) < 0.2. We propose a sequence of DIBs based on trends in their pair-wise strength ratios with increasing $f$(H$_2$). In order of increasing environmental density, we find the $lambda$6283.8 and $lambda$5780.5 DIBs, the $lambda$6196.0 DIB, the $lambda$6613.6 DIB, the $lambda$5797.1 DIB, and the C$_2$ DIBs.