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Because he may be a great communicator, mature for his age, and relationship minded, but he’s also, y’know, a BABY. Go in with your eyes open and appreciate the experience for what it is – a dalliance with the youthful exuberance of your past. “What do guys in their twenties really expect and/or want when contacting an older woman? That’s what I thought when I was a schmucky 20 something, and so did my friends.