A combined experimental and theoretical study is used to probe the conformational preferences of two flexible tryptophan analogs, tryptamine (TRA) and 3-indole-propionic acid (IPA). Resonant ion-dip infrared spectroscopy provides infrared spectra of single conformations of these molecules free from interference from one another. Density functional theory Becke3LYP calculations are used to predict relative energies for the conformers, while relaxed potential energy scans determine the barrier heights separating the minima. The different forms of the potential energy surfaces along the flexible coordinates for the two molecules provide a coherent explanation for the observed conformational preferences.