Written for Match.com

Email Encounters of the Second and Third Kind

What do you say after you say, “Hello”?

I’m brand new to the Internet scene as well as the whole dating scene itself. Not to brag but I get a lot of guys emailing me with the usual “You have a nice smile, let’s chat, etc.” I’m getting better at the initial encounters online, but it’s the second and third ones that stump me. When the guy says, “OK, I’m an open book, you can ask me anything,” I have no idea where to go from there. How should the second, third, etc. emails go? – Melissa C., 35, Middletown, Ohio

David Wygant answers: Welcome to the wonderful world of dating!! When someone emails you with “I am an open book,” go ahead ask them anything. Have fun, be flirtatious. Most people online are so afraid to cut through the small talk. I enjoy the adventurous types, and they are usually the most fun to flirt with. <

What I suggest is to go back over their profile and find two or three things that pique your interest. Look at what they love to do. If, for example, they say travel and music, then ask them to elaborate about their love of travel and music. Maybe ask them about some of their favorite places they have been. All the information that you need can be found on their profile – that is one of the wonders of Internet dating. Let me know how it goes, and enjoy the process.

Tina B. Tessina, Ph.D. answers: It helps a lot to know what you’re looking for. Not does he have blue eyes or a great body, but what are his interests, his love history, his life condition? You begin this by asking what his hobbies are, what he does for work, what his friends are like. Make sure you understand what you want to know, and ask questions accordingly. Then think about his answers. What are his favorite movies? What does that say about him? What music does he like? Ask questions about his childhood. Show interest in him, and be willing to share some things about you. Don’t start with the most personal stuff. The way to find out if you want to get to know him better is to find out what you can about who he is.

The Insightful Dater answers: You have to get creative and be willing to take risks in your communications at this stage. Be playful, curious and, if you feel comfortable, be flirtatious. What is it you want to know about someone you might meet? What they dream about at night? What they would do if they didn’t have to worry about paying bills? Do they give to charities or volunteer? What book is next to their bed? What was their most embarrassing moment? What was the first thing they learned to cook? You can create the dialogue you want. Have fun with it and learn about people. There is nothing more interesting than all the places someone else has been that you haven’t explored yet – be that a state of mind or an actual place on the earth. Have fun!