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But he took the plunge anyway.
Stern told listeners he surprised Ostrosky with an engagement ring in February 2007 — while they were naked in bed.
During his first marriage, he boasted of his fidelity while hosting strippers and porn stars on his show. Stern and his wife of 21 years, Alison Berns, had three daughters before divorcing in 2001. Their romance inspired his film "Private Parts."