The purpose of the study is to gain a better understanding of baby boomers' attitudes toward video chat applications and software based on their user experiences through the measurement of the level of use, usefulness, usability and aesthetics preferences. 133 participants recruited at a local public library and at three senior centers took the survey and 14 respondents were interviewed. The results of the study indicate: (1) Baby boomers have diverse attitudes and experiences in video chatting, but their attitudes do not present a significant difference from those of older generations; (2) Baby boomers' preferences for interface design are influenced by their psychological characteristics rather than physical changes; (3) Family members and close friends are a great resource for assistance and motivation for boomers. The knowledge of motivational factors and barrier factors could help maintain the existing baby boomer users and encourage potential users by providing an improved video chat experience design for them to connect with younger generations. This research could also lead social services into the telehealth age by bridging the gap between a traditional intervention and modern instant video communication.