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Dane Cook, a year-old actor has been dating year-old singer, Kelsi Taylor. Name required. In tenth grade, we made friends with a group of older guys who hung out on the main street of town, which ran parallel to the local university — guys who'd once gone to our same high school and had never left the social scene. The upshot of these films is broadly speaking the same. I'm 44 now, married with a daughter of my own. There were teachers who let me embarrass myself with clumsy childish flirting but never encouraged me for a teenage girl dating older man.