Why Detectives Write Better Messages

People will read your message like detectives. They’re looking for clues beyond your message’s literal interpretation so they can figure out who you really are.

Before sending your message, think of what conclusions a detective might arrive with. Doing this exercise will greatly improve your messaging.

Below is an example of an opener I see way too often on OKCupid. Put on your detective fedora and try examining it yourself. And remember, everything is a clue to a sharp detective.

From: Chillguysteve To: SoccerGuurl87

AGO text

Now, here's how I would analyze it.


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His message made its first appearance in the SoccerGuurl87's inbox. And the first thing she'll see is his emboldened username. This makes his username a large part of his first impression.

Steve designates “Chillguysteve” as his first impression. Think about what would motivate Steve to choose a name like Chillguysteve? Why can we safely assume Steve doesn’t use “Chillguysteve” as his handle on any other non-dating site?

Steve saw his username as an opportunity to explicitly pitch himself as a “chill guy” (mind you, most dating sites already have a designated area for pitching oneself). People who try pitching themselves in their username come off as desperate because they're worried the rest of their profile or message won't get read otherwise.

Unfortunately, “Chillguysteve” is weak evidence that Steve is “chill” – a word too vague and generic to make a meaningful statement about his personality. This shows he's not very good at pitching himself in the first place.


Hi SoccerGuurl87

The “Hi” is passable, but there’s no value in repeating her username “SoccerGuurl87”. In person, repeating her name may show he remembered it, or that he recognized her, or that he's addressing her and not someone close by. But online, both their usernames unambiguously loom over the conversation, readily available for either of you to reference. As a general rule, putting in effort to write low-information openers reveals you're overly interested and mediocre social skills.

He finishes off the greeting by proclaiming “my name is Steve”. At this stage in the interaction, there’s no need for her to know his real name. She'll assume your high interest level caused you to disclose irrelevant information about yourself. And if she's not at least as interested back, she'll lose attraction.

Small-talk Question

How’s your weekend going so far?

Steve segues from the greeting to a safe, small-talk question. Other examples include:

  • "How are you today?"
  • "How is your evening?"
  • "Did you have a good day?"
  • "How are you?"
  • "Anything fun planned for the weekend?"

These small-talk questions aren't motivating to answer if she's not already very interested back. Guys can't skip the game, chances are she isn't very interested at the start of the conversation. Small-talk might be useful in real life, but not online.

These questions are also generic/cliche. Asking generic or cliche questions offers no interesting clues about the person behind the keyboard.

Explicit Explanation

I saw your profile and thought I would message you. You seem interesting and we have a lot in common.

Steve designed the next line to explicitly explain why he’s messaging her, which makes him reek of insecurity. If he was more confident, he wouldn't feel the need to explain himself. SoccerGuurl87 can already deduce he finds her interesting by the fact he messaged her in the first place.

More examples of common "Explicit Explanation" lines:

  • "I saw your profile and thought I would message you."
  • "It seems like we complement each other very well and are looking for similar things in a significant other."
  • "It is hard to find quality people on here and you seem like you have your act together, so I thought I would give it a shot."
  • "I think you’re super cute and you seem like you might be cool."
  • "I just read and really enjoyed your profile and very interested Also you are looking amazing and very beautiful."

Caveat: It’s actually good to express why you’re interested in the person, but you shouldn't explicitly explain that it's the reason why you messaged them.


I love hiking, biking, beaches, music and movies. What are your hobbies? I’m really driven by my career and always love trying new things! I just moved to the city for a new job as a senior account manager for an internet company.

In the next few lines, Steve writes a self-summary that should’ve been in its designated area on his profile page. If this information is already accessible from his profile. This comes off like he's worried she won't visit his profile - a sign of insecurity.

Closing Statement

I hope my message and profile catch your attention enough to hear back from you.

The closing statement is designed to explicitly communicate the next steps. Steve’s closing statement, wordy and tucked underneath a mound of words, comes off as a meager and apologetic attempt at escalating the relationship. And once again, guys can't skip the game. Asking for next steps in an opener will almost never work. Other examples of closing statements you should avoid:

  • "Looking forward to hear from you"
  • "Please check out my profile and let me know if you like what you see :-)"
  • "By any chance would you like to grab some coffee some time?"

His closing statement gives SoccerGuurl87 many clues that Steve don’t feel he deserve his request to be fulfilled. She interprets the mound of cliches and redundant info above the closing statement as a try-hard attempt to justify his request. She knows he don’t derive intrinsic value from writing the BS word-cloud above. She now knows exactly why he wrote it and that reason is explicitly defined in the closing statement. Making his closing statement in the opener rendered the rest of his message’s content as an embarrassingly effortful and indirect ploy to fulfill a single goal. Once again, he signals insecurity and feelings of unworthiness. This is also a sign he doesn't think what he's saying is good enough.


Have a great Monday :–)

Like the greeting, this is another low-information cliche that doesn’t offer any value or say anything interesting about Steve's character.


– Steve

Like the greeting and salutation, signatures don't show off personality and offer no new information. On top of that, signatures do double the damage. They’re a sign he may not be familiar with informal text communication in general. It makes his message come off like a formal email, which isn't the right vibe in an online dating conversation

As you can see, a bit of detective work can reveal tons of information about you. Sharpening your detective skills will help you write messages that better communicate what you want and avoid what you don't want.

And yeah, I was hard on Steve, but don't feel sorry for him, he and his message are both fictional :)