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The Art of (Online) Conversation

Gab. Chatter. Jive. Powwow. Babble. Rant. Prattle. Those are just some of my favorite synonyms for conversation. I love to talk (which is why I have a job in communications). Words are such an important part of life. They have the power to hurt and heal, to entice or encourage. And they are a vital stone in the foundation we build on in relationships — whether in our everyday lives or online.

I have found that it doesn’t matter if people describe themselves as shy or outgoing, everyone seems eager to talk online. Maybe it’s because there is something about getting to know someone. I know I enjoy the anticipation of finding a response in my inbox. I’m also very attracted to men who know how to use words well. Engaging, fun, well-written emails definitely stand out.

For example, last week I received an email from a guy who was all of those above-mentioned things. He mentioned my love of travel, showing me he’d read my short answers. He also told me that I seemed like an interesting person and wanted to know if I’d like to start conversing. Remember a couple of weeks ago when I said we lose nothing when we compliment someone? It’s true! His intentionality caught my eye. His message was complimentary, interesting and he took the lead in establishing conversation. I’ve responded and am looking forward to a fun conversation.

This is a convenient segue into talking about taking the time to contact someone. This process has created a lot of questions for me. As a girl, is it OK to send an email and see what happens? How long do you wait before responding to an email? Do you look crazy if you respond to someone within a half an hour of his or her email or uninterested if you wait a day or two? If they’ve read your email, why are they taking so long to respond? ( has a feature that let’s you see if and when someone has read your email.)

Online correspondence can be tricky. In some ways, it’s easier to reveal more about yourself via prose than it is face-to-face. It’s also easy to fall into the trap of revealing too much too fast. I can’t tell you how many times I’ve done this. I see definite value in sharing the situations of life that have shaped me. However, in an effort to be open and vulnerable, I’ve shared too much too soon. Lesson of online dating/communication: Over-sharing can either get you ignored or get you the “thanks but no thanks” email. (I’m curious how you all have managed sharing with others. Have you over-shared or feel like you keep things close for a while before opening up?)

Once you’ve made it through the above dance and actually established a rapport with someone, it can be more comfortable to hide behind your computer screen and not move forward. I didn’t have a hard and fast rule about how long to talk to someone before meeting him until I talked to my friend Travis. When he was dating online, he never let correspondence go longer than two weeks before suggesting a meeting in person or at least talking on the phone. I think this is wise and try to apply it as I talk to men. If the subject of meeting hasn’t come up after a couple of weeks, I’ve tried to be creative about how to make that happen. I mentioned to one guy that I was in a cooking club. He responded that he’d like to try my cooking. I responded with the fact that I don’t cook for people I don’t know, and he caught the hint, asking when we could meet face-to-face.

What I’m discovering in this process is words do help. Reading how someone expresses himself says a lot. And while conversation online can be a great gateway to getting to know someone, it’s important to take that next step of talking on the phone or a face-to-face meeting before hearts get too attached. As in offline relationships, it’s important to be wise with your heart and emotions. I’ve found that I can get fond of someone through email and then when we meet offline, I am disappointed that the connection I felt through our online conversations isn’t there.

So talk to me! What are your thoughts on email conversations? If you’ve dated online, how long did you wait to meet someone in real life? Anyone have any great conversation pointers that have worked well as you’ve communicated online?

Guys, what has made you take that initial step to message a girl? Girls, have you ever initiated conversation? How long do you wait between emails?

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