When we as humans talk to a friend or a stranger or a significant other, we change our behavior according to what the social circumstance demands. What about songbirds? Do they modulate their singing depending on whom they're singing to? We investigate this question in the brown-headed cowbird (Molothrus ater), a model organism for studying the neuroscience of complex social behavior. Under the framework of honest signalling, the ability of the male to sing with high quality is a cue to the female which gives information about his possible potential as a mate. We find that although the visual display component of the cowbird song varies drastically depending on whether the male cowbird is singing to another male or to a female, confirming past studies which have found that the wingspread of a male when singing is much larger when singing to another male, the acoustic component remains remarkably stereotyped, a surprising finding given the level of neuromuscular precision required to repeatedly produce the same song. However, we find a downward correlation between wingspread and variance of song features, indicating that it may be easier for the cowbird to accurately produce a song when the wingspread is larger. This supports a type of handicap hypothesis, which speculates that males may intentionally handicap themselves when signalling to females in order to demonstrate their superior evolutionary fitness during sexual selection.