How to Write the Perfect First Message

Okay, I’m just going to admit it, and come out and say it. The first thing you read in the post was a bold face lie. I don’t actually know “How to Write the Perfect First Message”, and since I’m being honest, the title of this post is mostly for SEO reasons. I need this, no, WE need this to be a PSA for guys of the internet who are doing online dating, on how to send a first message. If I was being honest with the title of this post, I probably would have called it something like “How to write a good first message according to what Single Steve thinks is a good first message, but I’m not really sure you should take my advice because I rarely get responses to my messages”. So, as you can see, it doesn’t really have the same ring, or appeal to someone searching on how to write a good first message for online dating.

I decided to write about this topic for two reasons.

  • Guys need to know that when they send super generic messages, women can tell they copied and pasted that exact message to lots of other women. AND THEY HATE THAT AND WON’T RESPOND TO YOU IDIOTS.
  • I want to see if the structure of my messages that I send out is actually good?

Since I write a blog about the good, bad and funny of online dating, a lot of my female friends send me a lot of their good, bad and funny interactions from online dating. Most of them falling into the bad and funny categories. It’s actually slightly enraging to read some of these messages that these guys are sending to some of my female friends, only because all I can think is “HOW THIS IS MY COMPETITION!?”. Especially when I receive screen shots of first messages like the one below :


I can’t even. I literally can’t even. I just don’t understand. Like, when guys send these messages do they honestly think that the women they are sending them to don’t know that these aren’t just copied and pasted messages and sent in masses to lots of different women. I mean, they must not right? They must think they are so fucking clever sending these copy and pasted messages to lots of women a night. That, somehow they are “beating the system” and not really having to do any work, other than craft a single super generic message and send it out dozens of times. Because if they actually thought that the women they were sending the messages to knew that these were generic messages, they wouldn’t be sending them right? OR do you think these guys just don’t give a fuck and actually want to attract the type of woman that also doesn’t give a fuck that they didn’t actually read your profile?


Maybe we can make this a thing? Like next time a guy sends you a super generic message on online dating you respond with nothing else except a link to this post, letting them know, that you know, his message was a piece shit.

It’s already working! These are two screen shots already submitted!

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    So now I’m going to share with you how I craft my messages that I send on online dating. I don’t know if I’m exactly qualified to do this, because my response rate is about 15%, but I consider myself above average emotional intelligence and understand, at least in theory, what women would like in first message. I think?

    And like anything in my life, I probably approach sending messages on online with a little too much “engineering”. Meaning I have objectives that I try to meet with each message that I send.

     How to Send A Great First Message, According to Single Steve, Who Never Gets Any Responses

    Objective 1: Prove that you read her profile
    This is by far the most important objective, I would think female’s are looking for a guy that actually invested the time to read her profile before he decided to send her a message. How I demonstrate I actually took the time to read her profile is by commenting on something specific mentioned in her profile (DUH). Typically, it’s something complementary on something she has mentioned as a passion, interest or career.

    “That’s awesome you teach 6th grade! I loved 6th grade so much, I took it twice!”


    Objective 2: Show we have similar interest/things in common
    Okay, you’ve proven you’ve read her profile, now you need to demonstrate you actually have things in common. Mentioning shared interest helps create the buy in, she needs to relate to you.

    “OMG You love Starwars too!? I once dressed up as Luke Skywalker for 6 months straight, prior to the release of the Star Wars: Episode III Revenge of the Sith!”


     Objective 3: Start a conversation
    The goal is for her to respond back to you right? Well in order for that to happen, you have to ask her questions. Preferably, open ended questions, in regards to her profile. She will be more likely to respond if you ask her about something mentioned in her profile, as opposed to a random question you want answered.

    Good Example:
    I see you’ve run a couple marathons, that’s awesome! I’ve actually ran two as well. Are you currently training for another run? What’s been your favorite race you’ve run so far?

    Bad Examples:
    How many kids do you want?
    I noticed in your profile you didn’t mention your credit score….what is it?
    How many sexual partners have you had?

    My examples are jokes. Calm down. BUT WAIT, there’s more.

    Other tips:

    Never Mention Physical Complements
    Just don’t. You wouldn’t be messaging her if you didn’t think she was attractive. If you mention the words “Sexy”, “Gorgeous” or “Stunning” in your 1st message, please knock that shit off. There absolutely is, that one girl that is an egotistical maniac that loves hearing stuff like that from strangers on the internet. But for the most part, to most women on dating websites, it comes off as corny, creepy and repetitive.

    Keep it short
    You don’t want to write so much she loses interest. It should be short, concise and have questions, so she can have the opportunity to respond.

    Don’t try and be funny
    I’ve seen SO MANY messages from my female friends of guys trying to be sarcastic or use humor in their messages, but since their idiot cavemen it comes off as rude, cynical or awkward. Like I see what they were “trying” to say in their messages, but since they don’t know how to write it just came off as rude. If you are able to convey your humor in writing (LIKE ME), then by all means, go for it, but it’s probably safe to say since she’s never met you, conveying funny in messages may be difficult.

    Be literate
    Ironic coming from me, since I don’t proof read or edit my blog. But believe it or not I actually re-read my messages many times, checking for spelling and grammatical errors.

    Here are a few screen shots of a few of the last messages I sent out. I love feedback, as long as you’re not a dick about.


    Also, I assume what I write actually matters. I assume that I should actually be TRYING to write a quality message because the content of the message is actually going to be read and weighed in the decision process of whether or not she will be responding back to me.

    It’s actually kind of why I’m writing this post. Be honest, does it fucking matter?

    And if it doesn’t, that’s fine, I get it, the attractive guy who just writes “hey” will get a response, only because he’s attractive.

    BUT, here’s what I offer as my two cents of advice:
    Women, you should absolutely only respond to guys you find attractive, but beware of ANY guy who won’t even spend 5 minutes to read your profile and send you a personalized message. It COULD be a tell-tale sign of things to come in the relationship. What’s to make you think he’s going to spend 5 minutes in making sure you’re having a good day, or 5 minutes to do something else thoughtful?

    I wonder how many good, lasting relationships started with a copy and pasted message he sent to 15 other women that same night. You were just a number in his numbers game, he just happened to be attractive. If you respond to “Hey”, don’t be surprised your relationship is nothing more than “Hey” level. You, deserve, better.


    • emily February 4, 2015 at 11:06 pm

      God, I hated online dating because of that crap. Guys did not try whatsoever and then would send up follow up emails about all girls being bitches because I didn’t answer them. I mean, I can’t imagine why no one got back to them.

      Your messages are nice. The only thing I can imagine for why you’re not getting responses 100x more is because niceness is rare and extremely suspicious on a dating site. Way too often I responded to messages like that for them to go “oh ok that’s nice but god damn you’re just too sexy to be that smart” or something equally terrible, so even when I was just reading the examples you gave I was immediately apprehensive and wanted to know your ulterior motives. Unfortunately that can’t be helped, but like I said your messages are nice and I would have replied!!

      • Single Steve February 5, 2015 at 5:57 am

        You didn’t respond to their generic messages!? Well then you must be a bitch. Guys are the worst. Thanks Emily!

    • Renee February 5, 2015 at 2:07 am

      Yes Steve, it absolutely matters, we get that copied, pasted, generic shit all the time (as in, 20+ messages a day like that, which I have to bulk delete, hoping a great message like yours didn’t get caught up in the bullshit! Your messages were respond-worthy, and I always take the time to actually….RESPOND to them. Perfect advice, really. And yes, don’t mention the physical qualities in the first sentence- a great idea to relate to something (ie: the grad school) and ask a question, it makes you a person and not a DICK -> (as defined by their emails: “HEY LIKE YOUR SMILE.” (and that’s it?) or “WANNA FUCK. ” with the last name from email I got, by a man named “ILUVBYMYCOCO.” Thank you steve for setting them straight, you will be famous based on I’m posting this link on 1200 responses (copy and paste of course).

      • Single Steve February 5, 2015 at 5:59 am

        Oh, so that’s why I couldn’t get the screen name ILUVBYMYCOCO. Thanks Rene!

    • Pam February 5, 2015 at 2:30 am

      Hi Steven, Thankfully I am not single anymore after finally going out “as a friend” with my husband of 4.5 years after turning him down for coffee about 4 times. I do believe I could write a book about the bizarre experiences and people I met. Feedback on your messages: I believe it is “rooting” for the team. I actually looked it up just to be sure. I hope it isn’t just a difference in ages, but the f word would be a turnoff if said interested woman came and looked at your blog. Please continue to be a conscientious dater and instruct others. I have single friends out there who would like to find a good one. I hope I spelled that long word right.

    • Kelsey February 5, 2015 at 3:16 am


      I seriously have an epic collection of copy/paste messages. Also, my profile always had the disclaimer “I don’t always detect your copy & paste messages. But when I do, I delete that shit with the quickness.”

      • Single Steve February 5, 2015 at 6:01 am

        BLARG! Well there’s still time to send me said epic collection. SOLID disclaimer. Remember that time I messaged you on okcupid and I told you to get hit by a bus? Good times…

    • Divorced Kat February 5, 2015 at 5:26 pm

      Great tips! Even if I’m not even slightly interested in a guy, if he puts in this much effort, I will always reply, even if it’s just to say “thank you so much for contacting me but I’m looking to meet someone who lives closer to me” (or whatever).

    • Clare February 10, 2015 at 2:24 am

      Oh dear, if only this had been posted before I quit online dating. I would’ve had so many messages to send in. Some guys really don’t try, and it’s refreshing when you get a message that seems like they read your profile and want to get to know you. If I had a dollar for every generic message I was sent, I’d have a whole wad of cash. Some guys get so pissed too when you don’t respond. I feel like saying, “Why would I respond to a message you’ve probably sent to 20 other girls today?” The worst I was ever sent was on OkCupid, and a guy legit said, “Are you looking for a good little slave boy?” I didn’t respond, and then he sent another message saying, “I don’t mean in a sexual way”. I don’t even want to know what he meant.

      There are times where it’s tough when someone sends you a nice message, and then you respond, and they respond back with “Yeah you’re really sexy btw”. Like seriously?!

      Your messages were really good Steve, thoughtful and sounds like you took the time to tell them stuff you have in common. You will find a great girl, I know it!

    • J February 15, 2015 at 12:57 am

      I totally agree with your advice Steve. Just started this online dating journey since January and I’ve naturally been doing what you say (mentioning something in the profile, asking a question, relating things we have in common) and then I wait…Not putting my hopes in one person, I do this, careful to customize to each girl. They all are interesting and the ones I choose would seem cool-only if they would respond! It’s sad to see that they read the emails but no response. So far, I’ve gotten 2 responses, but now I’m back on the waiting end. I know they’re out there, but they might already be jaded by the other junk they get on a daily basis. Bleh. I guess the only flaw is that you should ask at most 2 questions. Like this comment, I’ve already written too much! Your site is funny and true, btw.

    • KC February 27, 2015 at 5:38 pm

      Yes, copypasta sucks! But it’s like the Nigerian prince scam, right? The initial effort is so low that it doesn’t matter if it only works 1% of the time.

      You may not realize it, but you have at least one spelling or grammar error on each of your messages. It’s not a big deal to some people, but could be a disqualifier for others. But I think a bigger problem is that your messages sound stilted with the “How was your weekend?” opener. That’s the line you use on your coworker, not on someone you actually want to get to know. 😉 It also sounds enough like copypasta that someone might not read further. I’d lead with the more personal and interesting observations/questions first. You want to sound fun, not formulaic. You have an MBA, right? Online dating is an exercise in marketing. What is your target demographic? What are their needs? What does your brand have to offer? “I actually read your profile” is a great start.

    • SingleJane March 25, 2015 at 6:07 am

      am I the only one who gets messages from guys tht say “Hi” and nothing else? I never even reply to those either….

    • Tom September 29, 2015 at 12:40 pm

      I have done this Steve… And I believe I have done this very well. I get no responses from the Ladies I try to converse with. Although I have received some very interesting responses to my profile. But it seems my appeal for those ladies commenting on my profile is just not there.
      I’m starting to learn that Online dating is for the hideously ugly only.
      I’m not hot and I’m not ugly. I am average. But why do I attract the hunchbacks of notre dame? haha

      • Tom September 29, 2015 at 12:44 pm

        btw. Before I get blown up… I’m not so shallow that I am going for just looks…. Just don’t want to be scared every time I look at her.

    • Joe December 27, 2015 at 1:52 pm

      Love your site man but you are trying too hard. The bottom line is no matter how creative you are the woman wants to see what you look like and how tall you are. Even if you pass those requirements you have to message her first and it does not matter what you say. Just don’t ask for sex right away and talk like you are literate.

      I’ve gotten messages from women that are witty, it’s clear they read my profile etc but I don’t care because of their appearance etc. Shallow yes but women are no different. It’s an uphill battle but the initial time connecting is based on shallow stuff and the mans ability to be positive and polite. It’s just harder as you age.

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