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Step 6: The Email Dialogue

Thetwo keys to online dialogue are inquisitiveness and humor. Have you ever had aconversation with someone who doesn’t ask any questions? I can’t stand that.After I get sick of holding up the conversation single-handedly, I just stopasking questions, and the conversation dies. People who don’t ask questions intheir messages are just as annoying. When only one person asks questions, it’snot a conversation; it’s an interview.

Comingup with good questions can be difficult, especially when you know nothing abouta person. To get started, you can ask questions about the other person’sprofile. Ask them about the things in which they seem to take pride. Answeringthose questions will make them feel good about themselves, and they’ll belikely to give full answers, which will facilitate the conversation. Ask themabout the aspects of their profile that most intrigue you and the parts thataren’t fully explained. Don’t be afraid to throw in random questions, e.g.favorite/least favorite holidays, best party trick, memorable vacations, dreamcar. If you’re really stuck, you can fall back on getting-to-know-you standbys:What do you do? Where do you live? Where are you from? How many siblings do youhave? But try to avoid these, or at least sprinkle them in with other morespecific questions. After you get responses, follow up with more detailedquestions that build on the responses. Avoid topics which might make peoplefeel awkward: dating, politics, exes, personal issues, relationships, etc. Youcan talk about these things once you’ve gotten to know each other a littlebetter. Such advice might seem obvious, but I’m often surprised by how peoplewith solid conversational skills don’t translate those skills into email.

Inresponding to questions, try to avoid short answers that shut down lines ofconversation. The more extensive your answer, the better the other person willunderstand you and the more material they’ll have to advance the conversation.Within reason. If you answer a simple question with several paragraphs, they’llthink you’re self-absorbed. If you’re asked a question that would take too longto answer, explain that you’d be happy to discuss it once you know one anothera little better.

Humorand wit separate great dialogues from good ones. In my best email exchanges, Ihave learned little information about the other person because our dialoguesconsisted mostly of wordplay and witty banter. You know an email exchange isgoing especially well when you make one another laugh. But don’t worry if thatdoesn’t happen. Email chemistry is not necessary for conversational chemistry. Somepeople just aren’t great writers. Conversely, great email chemistry doesn’tguarantee personal chemistry. A woman that I once dated wrote me email messagesthat would make me laugh out loud and vice-versa, but when we were together, wehad nothing to say to one another. Think of the email exchange as a filter. Youcan use it to determine a basic level of compatibility and weed out people whoare wide off the mark, but it’s not sufficient to determine actual datingcompatibility.

Don’tbe surprised if your correspondent asks you to write back to a regular emailaddress. Some people would rather not login to e-dating sites whenever newmessages come in. It can be awkward at work or at public terminals. You mightwant to set up a special email account that you use just for e-dating,especially if your regular email address has identifying information, like yourname.

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