If you really want to win someone's heart, take your ukulele to his house at night and serenade him under his open window. When you serenade someone, you play or sing a song, often outdoors.
In Italian, serenata means "an evening song," and the noun serenade is a tune played or sung, either for one specific person or for a larger audience, outside. It's still a serenade if you sing in the daytime, but the classic example of a serenade is a man singing below a woman's window at night. The word serenade can be both a noun — the song itself — and a verb — the act of singing or playing the song.