Delving into his past can help bring you closer.
It's definitely not the type of light and airy chat you want to strike up on your first date. Let's be honest: Dredging up the past and owning all things that went right and wrong is about as pleasant as having a root canal.
But precisely because spilling the beans requires such a high level of comfort and trust, a Q&A session (topic: all things past) with your guy can bring the two of you closer in your dating relationship. And everything from the way he responds to your dig for details to the answers he gives will provide you with clues to help you determine if this love's built to last.
Make the get-to-really-know time fun by asking a mix of questions that conjures memories both good, downright hilarious and, well, maybe not so good. Just be ready to openly discuss your past, too. After all, this isn't an interrogation.
Here's a list to get you started.
1. What were you like as a child?
2. What's your happiest memory of growing up?
3. What's the biggest lie you ever told—did you get busted?
4. How many sexual partners have you had?
5. What's the riskiest thing you've done in life? Sexually?
6. Why did you and your last partner split?
7. What disappointed you about your last girlfriend and led you to want to break up?
8. Are you still friends?
9. Who are your best friends in life? Why?
10. What's the most unusual place you've had sex?