John Cordero says fear of rejection makes men default to safe compliments that don't signal real interest. To avoid the nice guy trap, embed clear flirtatious intent in conversation instead of generic praise.
Chapters
So I actually have it this time. The power of my ancestors. This has to work this time.
All right, so the first thing I have to point out is the thing that is actually stopping you from flirting in the first place. And if you can fix this, you will give yourself a way better chance to show you are not just a nice guy. The thing that is stopping most men from flirting is fear. They start to think, if I show that I like her, she might reject me. And that concern or fear is is exactly why you might try to go to the safe route. But saying nice things isn't flirting. That's why you have to show intent inside the conversation.