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Depends on how the conversation is going. How long are the private messages? Does you profile contain enough info about you? In general most guys seemed to ask me on message 3 (sometimes two).
Too soon for me. I liked having an actual conversation/dialogue (no small talk) online and then a phone conversation or two before meeting. I never once met anyone without first talking on the phone.
Location: IN>Germany>ND>OH>TX>CA>Currently NoVa and a Vacation Lake House in PA
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Ask when it feels right. It will be different in every situation. You can't write a manual about this stuff, which is why so many people fail.
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