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About The Author


Emily Straubel

Emily is a sex and dating crusader. She founded The Red Lipstick Project as a place to talk openly about dating and sex and to connect with other intelligent women who want to find relationships that are as passionate and ambitious as they are. Emily also works with these women as a certified Holistic Health Coach to focus on their health and mindfulness as they go through breakups, job changes and other transitions to feel and look amazing in their own unique bodies. To share your story or experiences with dating in Portland email her at

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Posted: August 6, 2014

The biggest online dating mistake everyone is making. Please stop.

These words, when combined, are the most useless, overused and pathetic pickup line in online dating.

Written by: Emily Straubel
Worst Online Dating Mistake | Red Lipstick Project

I am currently writing a book called “Conscious Online Dating” to help smart/awesome people write better online profiles so they feel authentic and confident while dating online. This means I am in the midst of doing very serious “research and development,” which is not serious at all, of course. It requires chatting with a huge variety of people and going out on good and bad first dates to figure out what does and doesn’t work. It’s kind of amazing.

One glaring mistake has unexpectedly risen to the top of the pile of WHAT DOESN’T WORK and it’s such an epidemic that I can’t wait for the book to come out to talk about this. People need to hear about this now.

I noticed it after sitting down with a coaching client of mine to review his profile. He was feeling frustrated because, although he was finally connecting with great women (after some serious work on his profile), he wasn’t getting any responses when he reached out to them. He is an awesome guy and a great conversationalist, so I was curious to help him figure out where he went wrong. When we opened his messages it became very clear what the problem was. And it was sooooo easy to fix.

It’s not an issue that’s unique to him. I call this an epidemic (which is only a slight exaggeration) because 120 0f the 156 messages in my inbox fall into this category. This doesn’t include the pornographic or spammy messages that get immediately deleted. How do these people expect to stand out when 120 messages sound exactly the same? They each get exactly the same response:

Complete silence.

So if you are one of these people – don’t give up hope! You still have chance, not just with me, but with any potential partners. So go back through your old messages and resend a thoughtful message to anyone who you connected with and said the following words to – for these words, when combined, are the most useless, overused and pathetic pickup line in online dating:

“How are you?”

There are also a few variations on this theme:

  • “Hey, what’s up?”
  • “What’s going on?”
  • “How’s your Monday?”

When I read this message from a new guy, I am not motivated to respond. Quite the opposite, I’m motivated to go do something worth writing about. When you use those words, it sounds like you’re saying, “I’m bored, entertain me!” If you are bored, you are boring. You don’t deserve my time to respond.

It takes 30 seconds to scan my profile, pick out a simple detail and comment on it. “Hey, I like The Kinks too!” is only slightly less lazy, but at least it’s personal.

Even better, add a personal question that makes me feel like you didn’t just cut and paste some text from another conversation box. “Hey, I like The Black Keys, too, have you ever seen them live?” Yes I have and I will tell you the story over coffee and then it will become an inside joke after our third date. It doesn’t take much to make a personal connection. Just a teeeeeeeny smidge effort.

And the payoff is huge. Because there are so many lazy people dating online, you immediately rise to the top as “one of the good ones” or what I call a “conscious online dater.” Because you’re awake! You show up for life! If you can’t show up for a simple conversation online, why would I think you could be present, open and honest in a real live relationship (or one night stand)?! Maybe that seems like a stretch, but it’s true. I’ve experimented with whether there’s a correlation and I’ve found great conversations lead to great first dates – and lazy conversations lead to boring ones.

Even if I’m attracted to you and I think we would totally hit it off, there is literally no response to “How are you?” that makes me sound as interesting and attractive as I am in real life.

You have one chance at a great first impression when online dating, so make it worth it!

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