Promoting the re-employment of young and elderly people and realizing the silver dividend is an important part of the implementation of the national strategy to actively respond to the aging of the population. With the rapid development of the digital economy, the digital divide has seriously affected the elderly’s right to equally enjoy digital dividends and hindered the young urban elderly from choosing to re-employ after retirement. This article focuses on the digital divide, selects the China Family Tracking Survey data in 2018 and 2020, and empirically tests the impact of the digital divide and other characteristic variables on the re-employment choices of young urban elderly people, and then uses machine learning algorithms to predict the future. Changes in the impact of the digital divide on their re-employment behavior. The study found that the digital divide will inhibit the re-employment of young urban elderly people, and the deepening use of digital technology will increase their probability of re-employment. In the future, more urban young and elderly people will choose to re-employ, and the impact of the digital divide on their re-employment behavior will be deepened. The research conclusions of this article provide new ideas for filling the digital divide of the elderly, releasing the secondary dividend of the aging population, and implementing the active aging strategy.