This investigative thesis explores the interactions and encounters of individuals using dating apps, examining how attachment styles and the big five personality traits shape their experiences. The study reveals that attachment styles do impact users’ experiences. Users’ different levels of experience exhibit preferences for different features. Long-term users show a greater appreciation for add-on features compared to new users. Among personality traits, agreeableness shows a positive association with meeting and forming intimate connections with other users, while other traits exhibit less consistent correlations. The findings underscore the importance of personalized user experiences and improved matching algorithms. This research contributes to the field and highlights the need for further studies to refine methodologies and explore interventions that can enhance the overall dating app experience.