In this study the location of vehicle to vehicle distance thresholds for self-reported subjective risk and comfort was researched. Participants were presented with ascending and descending time headway sequences in a driving simulator. This so called method of limits of ascending and descending stimuli (Gouy, Diels, Reed, Stevens, & Burnett, 2012) was refined to efficiently determine individual thresholds for stable time headways with a granularity of 0.1 s. Time headway thresholds were researched for 50, 100, and 150 km/h in a city, rural, and highway setting. Furthermore, thresholds for self-driving (level 0 automation: NHTSA, 2013) were compared with thresholds for the experience of subjective risk and comfort in assisted driving, similar to adaptive cruise control (level 1 automation). Results show that preferred individual time headways vary between subjects. Within subjects however, time headway thresholds do not significantly differ for different speeds. Furthermore we found that there was no significant difference between time headways of self-driving and distance-assisted driving. The relevance of these findings for the development of adaptive cruise control systems, autonomous driving and driver behavior modelling is discussed.