What are some songs about older guys dating younger girls?

Answer 1

Here's a few:

• Young Girl by Gary Puckett and the Union Gap (in this one, the older guy recognizes the inappropriateness of the relationship and is specifically trying not to date the titular young girl: "young girl, get out of my mind / my love for you is way out of line")
• You're Ready Now by Frankie Valli and the Four Seasons (the presumably older guy here has explicitly waited for the younger girl to become old enough to "swing and dance where the swingers swung")
• Happy Birthday Sweet Sixteen by Neil Sedaka (the age difference here is never explicitly stated and could actually be fairly small; how creepy the "when you were thirteen you were my funny valentine" lyric is depends on whether you think it's best measured in months or decades)
• Sixteen Candles by the Crests (the guy is presumably older since he says "you're only sixteen but you're my teenage queen", but it's never explicitly stated how old he is)
• Only Sixteen by Sam Cooke sounds like it could be this to start with, but eventually it's revealed that the singer (the guy in the relationship) was also 16 at the time and is now looking back at it from an incredibly older and wiser vantage point: "but I was a mere child of sixteen / I've aged a year since then"