Romantic relationships are vital for health, well-being and quality of life, and an increasing percentage of romantic relations begin via use of dating apps and subsequently progress to dates. In the present study we examined dating application use and dates among individuals with SAD (n = 54) and without SAD (n = 54). Our sample included young adults (age range 18 to 33) who were not in a romantic relationship at the time of the study. For both individuals with SAD and without SAD, half of the participants were men, and half were women. We used a daily diary measurement in which participants reported on their dating application use and dates, as well as on concomitant emotions and perceptions for 21 consecutive days. We found that individuals with and without SAD did not differ in the frequency/duration of application use nor in the number of dates attended. However, individuals with SAD experienced dates as more negative compared to individuals without SAD (Cohen’s d = 0.65). Interestingly, individuals with SAD did not significantly differ in their experience of dates as positive compared to individuals without SAD. Moreover, use of dating applications/going on dates were associated with increases in shame (Cohen’s d = 0.59) and embarrassment (Cohen’s d = 0.45) and this was found to a greater extent among individuals with SAD compared to individuals without SAD (Cohen’s d = 0.50, 0.39 for shame and embarrassment respectively). Findings are discussed in the context of cognitive behavioral models of SAD and implications for treatment are considered.