Three hosts in the GDCC and cucurbit[n]uril (CB[n]) families were chosen for the SAMPL8 host-guest challenge. We aimed to study modeling implication(s) of tetra-endo-methyl Octa-acid (TEMOA) and a variant tetra-endo-ethyl Octa-acid (TEETOA), with flexible ethyl side-chains in the presence of mostly rigid guests. In addition, SAMPL8 also revisits the cucurbit uril (CB8) host, with a series of guests which are addictive and commonly abused drugs .