The study was based on the first author’s model and assessment inventory of activity-related experiences and aimed to compare the experiences in a company, in lonely condition and in everyday work/study setting as mediated by one’s attitude to being alone. The data collected on three different samples (N=218) varying in their concern with communication/loneliness issue revealed slightly varying but generally consistent results. Respondents high in general loneliness differed mostly by their experiences in a social situation: significantly less meaning and pleasure and significantly more effort and void. Respondents with high dependence on communication experienced more void and respondents with high scores positive solitude experienced more pleasure and meaning in a lonely condition. Experiences related to work/study condition were significantly associated only with general loneliness (void positively, meaning and pleasure negatively) but not to specific attitudes toward loneliness. We also used the measures of Big 5 and Basic need satisfaction (N=77) that showed that general loneliness was slightly predicted by neuroticism and strongly by introversion and by frustration of basic needs for autonomy, competence and relatedness, dependence on communication by neuroticism, introversion and frustrated need for competence, and positive solitude just slightly by introversion and frustrated need for relatedness.