" The speaker probably used the simple past because he is asking about one "telling" event that might have occurred in the past. The present perfect is OK too, but it is not as focused on a particular event. Grandpa: Did I ever tell you the story of when I fell out of the tree?
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whatchadoinOh, did I tell you Joseph taught me to skateboard?It is common in English to preface new information you want to convey with "Did I tell you (that)?" It's really not necessary, but it's very idiomatic to say it. By the way, "Did you know (that)?" is also used this way.