“Remember Pam? She said, you probably going to get back with your ex. You still talk to her?”

3.       Ask invasive questions

Ask anybody who knows me and they’ll tell you that I believe in boundaries. I’m a little more complex than most guys because I’m very careful not to ask questions that would lead to similar questions being asked back. With that said, when you start to ask questions like, “Why did you break up with your ex-girlfriend?” on the first date, or “So I wanted to ask you about [that embarrassing story from college that they’ve somehow uncovered by doing a deep dive on your past],” you’re way out of line. When people ask me when is the right time to bring up the tough questions, I always say, “When they’re necessary, not when you feel like you need to know.”