Accurate baseline data are essential for researchers to determine an intervention’s effects yet may be affected by anticipatory anxiety and assessment familiarity. Familiarization sessions help establish accurate baseline data. High-intensity functional training (HIFT) elicits performance outcomes based on constantly varied workouts. It is unclear how familiarization affects anticipatory anxiety and workout performance among HIFT novices. Familiarization was hypothesized to decrease anxiety and improve workout performance. Sixteen college-aged subjects (62.5% women, 20.2 ± 1.14 years) completed one introductory and four sessions of the same workout. All subjects were recreationally trained with no HIFT experience. State and trait anxiety were assessed at the first session. During the workout sessions, state anxiety (SQALS) was assessed upon arrival at the gym (SQALS 1), after learning the workout protocol (SQALS 2), and when the workout concluded (SQALS 3). A significant main effect of the number of previous sessions on workout performance was observed (p = 0.011). A repeated-measures ANOVA showed a main effect of time on SQALS 1 (p < 0.001), SQALS 2 (p < 0.001), and SQALS 3 (p < 0.001). Our results suggest implementing two familiarization sessions for our HIFT-based workout was sufficient to decrease anxiety and establish a baseline measurement. Future research should examine if this remains true for other types of HIFT-based workouts.