Meeting People: Getting Conversations Started

I'm enjoying meeting guys through e-mail. I don't have any trouble talking about myself, my interests, hobbies, experiences, etc. But I don't know what questions to ask them to get them "talking." I'd like to learn more about these guys and draw them out more in e-conversation, but I'm feeling clueless as to what to ask them so that I can get to know them better. What questions do you ask? -- donnylyn Question:
ABOUT THE EXPERT

Sherry Amatenstein

Sherry is the author of The Q&A Dating Book and Love Lessons from Bad Breakups. She has taught dating seminars, appeared as an expert... Read more

Dear donnlyn:

It's hard to get someone virtually talking when the nature of cybercommunication (unless you're in "IM" mode) is relentlessly one-way. Certainly you want to know the basics about your boy: his age, height, weight, profession, marital status and so on. But here are five questions that can stimulate some insightful answers from your potential future honey:
  • If you were marooned on a desert island, what three things would you want to have with you?
  • If you could invite 10 well-known people (from any era) to a dinner party, who would they be?
  • Not to be morbid, but what do you hope your epitaph says?
  • Would you rather have fame, wealth or romantic happiness?
  • When was the last time you cried and what brought on the waterworks?
After you've read his answers to these questions, you'll have a pretty good idea of what makes him tick and whether or not you want to move the relationship from e- to telecommunications. Good luck. Answer: