Despite the clear benefits that social connection offers to well-being, strangers in close physical proximity regularly ignore each other due to their tendency to underestimate the positive consequences of social connection. In a between-subjects study (N = 49 pairs, 98 participants), we investigated the effectiveness of a humanoid robot, a computer screen, and a poster at stimulating meaningful, face-to-face conversations between two strangers by posing progressively deeper questions. We found that the humanoid robot facilitator was able to elicit the greatest compliance with the deep conversation questions. Additionally, participants in conversations facilitated by either the humanoid robot or the computer screen reported greater happiness and connection to their conversation partner than those in conversations facilitated by a poster. These results suggest that technology-enabled conversation facilitators can be useful in breaking the ice between strangers, ultimately helping them develop closer connections through face-to-face conversations and thereby enhance their overall well-being.