5. Whether he has a plan to settle down.
“I’m getting old enough that I have to think about my future with my next boyfriend,” said a woman in her late 20s who is getting desperate. If you’re pressed for time and don’t want to waste precious days by starting into a causal relationship, you may want to feel out his intentions for the future. This may be a difficult topic to discuss, especially during the early stages of your relationship, but it’s best to make things crystal clear, rather than face irreconcilable differences.