How to Start a Conversation Online

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Andy Crestodina

Every digital marketer does it. Some do it well. Others …not so much. But it’s a critical part of social media, online networking, and public relations. Let’s talk about starting conversations.

There’s an art to writing that first message. And there’s science behind that art. Dating websites have tons of data on what works in first messages. Let’s see what marketers can learn from the hopeful boys and girls on dating websites.

Ready? Ok, Romeo. Let’s go.

1. Mention Their Interests

In a study by OkCupid, they show that the member would get a higher response rate for first messages that mention the specific interests of the person they’re talking to.


This may be personal interests (such as zombies and metal bands) but in marketing, it’s more likely to be a reference to something professional, such as:

  • A comment on a topic that they’ve mentioned recently: “I saw your post/tweet/article about pinball…”
  • A prediction they’ve made: “I see you predicted that arcade games are making a comeback…”
  • An opinion you share: “I totally agree with you that 80’s games are underrated…”
  • A compliment on something they created or accomplished: “You’ve got the high score on the pinball machine at SuperDawg. Congrats!”
  • A thank you for something useful they shared: “Thanks for sharing that article from Flipper Quarterly. I found that really useful…”

Mentioning an interest is your chance to show that you have something in common, and to do it in a positive way. 

2. Show That You Did Your Homework

How’d you find that interest? You read their profiles, you’ve read their content, you’ve researched their company. You’re listening and paying attention.

Everyone likes to be noticed.


If you’re starting a conversation with a high-value potential contact, like a prospect, job candidate, journalist, or influencer, dig deep into the research. Indicating that you’re deeply engaged makes a huge difference.

  • I read your book, and I agree that…

  • I’m subscribed to your podcast and I noticed that…

  • I’ve been reading your blog for the last few months and…

3. Be Humble and Self-Effacing

For guys on dating websites, this is life and death. The ladies can smell arrogance a mile away. Self-effacing language shows humility. But it also acknowledges the obvious: it’s awkward to contact someone out of the blue.


Tip: A first message should be direct and concise. But if there’s a place for softened language, it’s in the one sentence that admits you’re coming at them out of nowhere.

4. Be Personal and Original

Another finding from the OkCupid study found that the most generic salutations get the worst results. “Hi” “Hey” and “Hello” were the most common openings, but also the least effective.


I’m not suggesting you start a message to a New York Times editor with “Yo!” The lesson here is this: don’t start by sounding like everyone else.

5. You can’t win if you don’t play …patiently

Any pickup artist will tell you that you’ve got to put yourself out there. Have the guts to reach out. No guts, no glory. But don’t rush it. It may be worth it to slowly put yourself on their radar in the days and weeks leading up to the first conversation.

Social media gives you all kinds of ways to do it. Here’s a sample of the 35 steps in the complete online networking guide

  1. Follow them on Twitter or Google+ (which don’t require their approval)

  2. Share their content on Twitter or Google+ (and mention them)

  3. Comment on something they wrote (show that you thought about it)

  4. Share content on Facebook or LinkedIn (and mention them)

  5. Write something that refers to them (and quote, link, or credit them)

  6. Start a conversation (possibly mentioning what you wrote)

Once the conversation has begun, ask a follow up question. Open-ended questions work best. Avoid asking questions that can be answered with a single word.

Once a good connection is make, you’re ready to politely ask for something. I find that an offer to collaborate is a great way to start.

Go for it, player! Ask her out!


Our friends at Bluewire Media created an excellent blogger outreach template. Enjoy!

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Comments (18)
  • hy andy crestodina nic post and great information so very thanks to sharing this post

  • Great post Andy – – definitely will be a kick in the seat to keep up with online networking (which I’ve let slide over the past week).

    Another great template in addition to Bluewire’s is the one from Groove’s blog:

  • Yo Andy! (That’s how we do it here in Philly. 😉
    Wonderfully insightful and conversationally presented. I love your writing. These 5 points marry well together. And this cat leaning on the pinball machine is cracking me up. Great stuff!

  • Hi Andy, that’s a great analogy you’ve used. Dating and marketing both require conversation starters (and expose us to the chance of rejection!). No wonder it can be a terrifying experience at times.

    Thanks for mentioning the Blogger Outreach Template too 😉

  • Hi Andy, great post. Thanks for sharing your thoughts.

  • I was scoffing, thinking to myself, “These are precisely the things that we’ve been teaching consultative sales people forever!” Until I read #5. Patience. That’s the missing ingredient with even some of the very best Business Development (you know they’re salespeople) Execs. Too many, including me, want that breakthrough NOW, so we force it with multiple messages, emails, etc. As George Takei suggested to Howard Wolowitz in one of my favorite episodes of the Big Bang Theory, “A lady (customer) wants to be wooed, courted slowly.”

  • Love the insight! And to those opening lines, using “so..” to begin…it’s just not so. As usual, great ideas Andy!

  • All excellent ideas.

  • Just started reading your blog and I just want to say thanks for all the great insight. Keep it up!

  • Hi Andy,

    I just saw your article about starting conversations on your blog today. I like conversations too. Really well done!

    How’d I do? 🙂 Great tips, Rog!

  • Amazing image to start the post. Just amazing, Romeo.

    • Thanks, Kurt! The research provided good substance, but that guy really brings the style. Who can resist a red turtleneck? She’s a goner…

      • I’m following your lead with my next post to the blog, should be live by next newsletter.

  • Love it! Who would have thought we’d be learning about social marketing from.. online dating. Andy – You always have great ways of bringing interesting seemingly unrelated ideas and ‘connecting the dots’ to create helpful tips.

    • I certainly wasn’t expecting it. I haven’t been on a dating website in a decade or more. But when I saw that research, it was just asking to be re-purposed. Of course, some things are less about the specific context and more about human nature in general.

      Thanks for the comment, Ayako! Hope your travels are treating you well…

  • So, Andy, have you field tested your ideas? 🙂

    • I have in the marketer outreach setting, but not with the ladies. I don’t think @Manamica would appreciated that!

    • Great insights, Andy! Sure brings back memories of all those awkward messages from my days on eHarmony years ago.

      curious to find out where “ni hao” would rank if they did a similar study for Chinese salutations. 🙂

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