Prior work has examined how users judge their smartphone use, typically focusing on either usage duration or intention. How these two factors jointly shape such evaluations remains unclear. We conducted a two-week study with 104 participants, who reviewed their screenshots and provided labels of both usage intention and evaluation of time use. Across 73,000 sessions (6.1M screenshots), the relationship between duration and evaluation was initially linear but then bounded: positive evaluations declined and negative ones rose with longer phone use duration but both eventually stabilized, most often judged neutral. Trajectories varied by intention. Entertainment mirrored the overall trend; functional use continually lost positive evaluations, whereas information-seeking became increasingly positive during the first half hour before later declining; messaging-based connections slowly lost positive evaluations, while social media–based connections declined more quickly; finally, “no specific intention” unfolded in phases—from short positive use to regret-prone mid-length episodes to neutral long sessions.