What's "wingman" mean?

Native speaker’s answer
Rebecca
In a literal sense, a "wingman" is a pilot who flies behind and outside the leader of a flying formation. Socially and informally, a "wingman" is someone who helps you maybe get a date or supports you in pursuing someone you're interested in, like a best friend helping his friend flirt with people at a bar. Here, the cover letter and resume work similarly since the cover letter supports the resume and helps one get a job. Ex: Can you be my wingman at the party tonight? Ex: He was a terrible wingman and flirted with the girl I was interested in.