First and second "guesses" refer to the phone offering you a classification type. Most of them have a sort of pulldown or scrollable menu with first and second (etc) options. Those are basically the people building the interface taking a guess at what type of number you're entering. Please answer for your personal usage, not how you think others
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I have some work numbers not because I call people about work, but because I sometimes need to contact them during the day about plans for the evening, or some such. It's a backup. It's a tossup whether I have more of those than home numbers though.
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