One of the most challenging parts of online dating getting the conversation started.

First you search. Then you find someone who sparks your interest. You find them attractive, you read their profile and think, hey this guy/girl sounds pretty cool. You click, ‘send an email’ just to stare at a blank page for 30 minutes. You have no idea what to say. Eventually, you type anything quick and easy just to get it done and over with.

Let me help you conquer that blank screen.

For starters, here is what NOT to do.

  • Do not just say, “hey” or “hi” or “what’s up?” or (cringe) “text me, 555.1234” No joke, that was a message I got once. Creepy.
  • On the flip side, do not introduce yourself with an autobiography. You have a profile for that (which is also not meant to be your whole life’s story). The odds are good that no one will take the time to read it all.
  • I’m not a big fan of winking or nudging or whatever passive aggressive option is available, but that’s a personal judgement and can be a case-by-case decision. Sending a real message shows confidence and genuine interest. To me, a wink signals that all the effort you can muster is a click of a button and hope for the best.
  • Don’t be generic and ask, so what do you like to do? Hopefully this person wrote all about that in their profile – that’s what it’s for. This might signify you didn’t take the time to read it.
  • Don’t ask, so how is online dating going for you? When you ask that it might generate the thoughts: Are you interested in me or my dating life? Are you interested in me or your competition?
  • Absolutely DO NOT compose a standard message that you copy and paste and send out to everyone. Believe me, people can tell. Similar to my first point, if you send the same message to everyone all it shows is that you are playing a numbers game and you’re not genuinely interested in the person you are messaging.

If you appear like you will just take what you can get, your response rate is going to be low.

I wish I had archived them all ‘interesting’ emails I’ve received. Please share your favorites in the comment section below, or on my Facebook page!

A good, genuine message is reflective and conveys authentic interest. Start conversations that are open-ended; get him/her talking about him/herself.

Here are some examples:

  • I enjoyed reading your profile, you seem X,Y, and/or Z (easy going, down to earth, smart, etc.) I like that because……
  • I like what you said about X, Y, and/or Z, and  I can relate to what you said about X, Y, and/or Z.
  • Be direct and say, I am genuinely interested in learning more about you (and maybe add a qualifier about what it is about her that makes you say that). Confidence is attractive.
  • Simply say, Tell me more about:
    • your trip to X
    • Your dog, your kids; whatever you are genuinely interested in learning more about.
    • You seem to love your job, tell me more about what you do…

The final step is to ask for a date. Remember, the goal of online dating is to get off line. Don’t ask for the date right away, but don’t wait too long either. My suggestion is exchange a couple messages first to warm things up. Don’t wait longer than a few days. If you want to play it safe and cover your bases, add a disclaimer that suggests you are respectful of whatever pace they are comfortable with.

There are a gazillion varying opinions out there. Dating has somehow gotten very complicated, but it’s really not. At least, it shouldn’t be! At the end of the day, follow your instincts, and most importantly, be yourself. Stay positive, take things in stride, and don’t forget to have fun!


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