Abstract Background Digital social interventions for older adults have become increasingly important due to their flexibility and potential to reduce loneliness. Digital games provide easy and fun interaction possibilities but need more exploration. Methods Using a mixed-methods design, we piloted a chat-based mobile application (PhotoSnake) designed to elicit social connectedness. Participants joined two in-person workshops two weeks apart and a focus group afterwards. They filled in a demographics and loneliness questionnaire pre- and post-intervention, and we collected anonymous in-app data. Results At baseline, participants (N = 15) were 74 years old, moderately lonely (Median = 2.0), partnered (40%), retired (93%), and living independently alone (53%) or with others (47%). Loneliness did not change over time. They valued the in-person workshops to get to know each other. Participants enjoyed playing the game for a few days but felt it lacked sufficient variation to persist gameplay. Furthermore, the in-app interaction mainly focused on the game and was perceived as too superficial to be meaningful. Conclusion This study helps design future digital interventions by showing the importance of in-person contact for engagement and meaningfulness. Players do not automatically label in-game interaction as valuable, and game design should focus on aiding players in creating personal interaction moments.