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OP you're over thinking things. If the nickname suits him, use it. If it doesn't, don't.
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My cousin is one of many Roberts in our family. To us he's bobby. To friends he's rob or bob now that he's an adult. I don't think it has to be one or the other. |
| My sister's asshole ex-husband is a Bobby. He's never gone by Bob or Robert. I may not like him as a person, but I never had an issue with calling him Bobby. |