How to hit on a stranger: two contrasting pick-up lines

Image: Édouard Manet via Wikimedia Commons

You’re going to need help from people you don’t know. Getting them to respond is like hitting on a stranger. Your pick-up line makes all the difference.

Two pick-up lines, two reactions

Two strangers contacted me last week. Each wanted a conversation. (Since they were personal messages, I’ve concealed the identities of the senders.)

“Lenny” starting hitting on me on LinkedIn:

Lenny: Hey Josh—I am leading and Ad-Tech start up that created interactivity [details removed] call [name removed]. Can I give you a call???

Me: I’m a writing expert. What benefit could a call have???

Lenny: Why–Are you a mute? If not, would love your perspective. I quote you a lot… What’s your phone number and is tomorrow good?

Soon after, “Elliott” tried to pick me up by email:

Subject: What got you to where you are now?

I am envious of your prolific writing ability, not to mention the no BS style. Your book can’t come soon enough.

Can we talk for 20 minutes?  I’d like to ask a couple of questions to figure out what makes you excel–and how I can get from here to there.  Presently I’m drowning in content from [identifying content deleted]—similar to the Outside In book you edited. My biggest weakness is that I don’t write nearly enough. My second biggest weakness is that I write too perfectly, and my third is that it is too academic.  I’d love to ask you a couple of questions to understand the mindset, habits, and tools that have helped make you great that I might be able to use as well.

If I were still in Boston I’d offer to take you to lunch/coffee, but alas I’m now in Seattle. When is a good time for you? You can send a couple of times or select a time that works for you.

I immediately set up a time to talk to Elliott the emailer, and had a great conversation. As for Lenny the LinkedIn guy, his whole approach put me off.

Why Elliott’s pick-up worked and Lenny’s didn’t

Brevity isn’t everything, especially when you’re contacting strangers. In 25 words, Lenny revealed two typos (“and” instead of “an” and “call” in place of “called”), a dubious triple question-mark, and no clues about why I’d want to talk to him. That’s the bar-side equivalent of bad breath and a cheesy outfit.

Elliott’s email, by contrast, warmed me up quickly:

  • He knows I’m a writing expert and mentions it.
  • He makes it clear he did his homework (by identifying a book I edited).
  • He states clearly what he’s looking for.

There’s also flattery, but frankly, that makes no difference. Anyone can say you’re great — it doesn’t prove they’re worth speaking with.

My instincts were right

After a bit of back and forth on LinkedIn, it became clear that Lenny was interested in me because of something I wrote about television 15 years ago. I only took his call to complete this experiment and report to you what happened. And although Lenny’s background on LinkedIn was impressive, the call was a waste of both of our time.

I had a more thoughtful conversation with Elliott. I’m always interested in what gets in the way of people writing better, and how they perceive their writing compared to its actual flaws. And our relationship is off to a good start: he’s considering me for an editing job.

Learn the lesson of Lenny and Elliott. If you’re trying to pick up a stranger by email or direct message, do a little homework first, and put a little effort into it.

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  1. Elliott respected you as a person and as a professional. Lenny did neither.

    Elliott obeyed the iron imperative: he didn’t waste your time. Lenny made you do all the work of figuring out what he was after. Bad breath and a cheesy outfit, indeed!

  2. What if, you are approaching a stranger face-to-face, rather than a call or an email? (A person whom you might have never met and nor known about). Could you help with some suggestions on this?

    1. Here’s a pickup line that nearly always works:

      “I’ve read your book.”

      If not book, then blog, or report, or presentation. That immediately says “I know who you are.” And people will talk to someone like that.