despairingly (adverb)

1. Despite his best efforts, the comedian looked despairingly at the crowd as they failed to laugh at his punchline.

2. During the Great Depression, many families lived despairingly as they struggled to find employment and feed their children.

3. The protagonist's sidekick looked despairingly at the impossible task ahead, wondering if they would ever come out victorious.

4. Standing at the train station, she watched despairingly as her lover boarded the departing train, unsure if she would ever see him again.