If you’ve not watched Randy Pausch’s The Last Lecture, I highly recommend it even if it has little bearing on this post other than the following passage:
“But the best story I have about my dad – unfortunately my dad passed away a little over a year ago – and when we were going through his things, he had fought in World War II in the Battle of the Bulge, and when we were going through his things, we found out he had been awarded the Bronze Star for Valor. My mom didn’t know it. In 50 years of marriage it had just never come up.”
It is 100% okay if your person-of-interest doesn’t know every single thing about you. You are entitled to keep some things to yourself. In fact, there are things you absolutely should keep to yourself. In the beginning, hold off on revealing the more controversial details. These things can be gently imparted when the time is right. Suppress the desire to regal him with all your great stories, ask him a question instead. Show him you’re interested in him, not just in having an audience. Always, always, always contain your eagerness to share every last detail of your day – there are far more interesting things to talk about.
Allow conversation to be a give-and-take with a natural flow. You will be more intriguing if you gradually reveal facets of yourself, stretching out someone’s surprise at getting to know you rather than laying all your cards on the table in one fell swoop.