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I don't know if I qualify as "older" and I don't know if my view is up to date on these things, as I am in my early 30s and been married 5 years.
And as an additional caveat, I am not originally from the US, although I have lived here the majority of my adult life. I say this because I am still somewhat puzzled by the whole "dating" thing, as it is a more formal way of courtship than what I am used to.
With those things in mind, there are many ways of letting him know you are not interested in him in "that" way without having to have the "date" conversation. I.e., get a seat at the bar instead of a secluded booth, don't dress up for a date, etc.
I don't think it you would be leading him on if you didn't have the "date" conversation. But then again, I think I come from a cultural background that is more similar to little tippler's, where there is less concern for labels.
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