5. You pester him to gather information about his best friend.
One frustrated man in his late 20s revealed, “It’s really offensive to know that she’s talking to me only to phish information from me.” Whether or not that’s your primary focus, relentless questions about his best friend will raise doubts in his mind. If that is indeed your main drive, it’s better to be honest and seek his support, rather than ruin your friendship in the process.