Research of face-to-face meetings between adolescents and people met online stands on untested assumptions that these meetings are uniform, and adolescents attend them to expand their social circle. It is also unclear what makes such meetings pleasant or unpleasant. This study examined meetings of 611 Czech adolescents (age 11–16, Mage = 14.04, SD = 1.67, 47.1% female). Face-to-face meetings attended with friendly, romantic, or instrumental motives differed from each other, emphasizing the need to investigate them separately. Pleasantness of meetings is closely related to disconfirmation of adolescents’ expectations. Unmet expectations related to unpleasant meetings, exceeded expectations to pleasant ones. While present findings uphold existing theories (e.g., social compensation), they also call for new theoretical perspectives for this common adolescents’ activity.