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The guy was pretty much my dream guy from what I could tell with the exception of one thing… It got me to thinking, how old (or young) is too old? I’m not a dating expert by any means so I turned to every other women I knew and here were some of the most popular opinions ranked. I don’t know if I’m comfortable with 49 as that is only a few years younger than my parents (sorry for spoiling your age on the world wide web! If you are comfortable, happy, and it works- age is nothing but a number. If you enjoyed this and would like to hear more about dating in Chicago, why don't you subscribe!