What NOT To Say In A First Email

Brenna Ehrlich and Andrea Bartz are the creators of the blog and book “Stuff Hipsters Hate.”

In a CNN article this week, they offer 7 humorous email openers that are guaranteed to keep you single. They claim that even if someone finds you attractive, “ironic mustache and all,” a bad first email can ruin your chances at romance.

Read the article here. On a more serious note, if you’re dating online, what kind of emails turn you off?

Join our conversation (20 Comments).
Click Here To Leave Your Comment Below.


  1. 1
    lux aeterna

    Humour aside, I think that list is pretty accurate! I’d like to add “The Extremely Loooong First Email’. Even if I like the person it makes me feel bad for not writing an essay back. Or is that the whole point? To guilt-trip people into replying? Uuh.
    My other guaranteed turn-offs are:
    – Bad spelling and grammar. If they are dyslexic, they should say so straight away. I once dated a guy who wrote ‘would of’. I cooled off soon after.
    – Hey what’s up?
    – Wow you’re so sexy/gorgeous/hot and no reference to anything else about me.
    – Sexual fantasy rambles (although they are great little gems to forward to my friends!).
    – Bland copy & paste message.
    What does work for me though is a short paragraph with a humorous reference to something on my profile, usually about my country of origin. Cheeky humour always works. It’s not overly personal, sexual or emotional but makes me smile and shows me I can have a fun evening with this person even if we have nothing in common. People who are too polite seem nervous and overly serious.

  2. 2

    I once had an e-mail from a guy on match.com that consisted of exactly one sentence:

    “Do you have a full sexy body photo you can send me???”    

    I did not dignify  it with a response. I blocked him from contacting me further & checked the “Personality” box as reason for blocking…. (because match doesn’t offer a “Perv/Horndog” box!).

    Also: In the same way that your online profile should be spell-checked & grammar-checked, your first few e-mails should be too. Leave the “G UR QT” comments/abbreviations for later.

  3. 3

    Oh, this is sooooo true.   I don’t even want to reply to the ones who just say “hi” or even worse. “Wassup?” And I often wonder if guys who write to say, “Your profile intrigued me. And you have lovely eyes” are saying that to everyone, but I usually respond to them after checking out their proflie and making sure they don’t creep me out someway.

    I’m afraid I have a tendency to be an “autobiographer”–but I’m working on tightly editing before I push “send”. I’ve been online a couple of weeks and haven’t gotten a date yet. Wonder how long it should take before I start feeling insecure and wondering what’s wrong with me.   I just posted a great picture this morning, so hopefully things will pick up.

    Love your blog, Evan!   

  4. 4

    2 things get an INSTANT delete – all else is considered:

    – blatantly about sex
    – long winded all-about-me canned note “here is my whole life history that is over 200 words long that I copy and paste to many people with no consideration to why I am writing”

    I can get over a lot – not everyone is a good writer – but those are horrid!



  5. 5

    Anytime the phrase, “You won’t be sorry” shows up in a profile or email, I  feel like  “sorry” is exactly what I’d be if I went out with them.

    If they have to sell themselves like the latest product on an infomercial, it’s a turn-off.

  6. 6

    Seeing that I’ve probably been doing this longer than anyone I’ve learned 2 things that are fairly simple and universal.For men as long as their opening email isn’t “sexy creepy”,a blatant “form letter” that looks like it’s sent to everyone,or “gushy complimental” you’ll at least have “a chance” to get a reply if you qualify in looks,height,education,job description/income…..and other stats that may be individually important to that said woman specifically. In other words if a guy is lucky enough to be in  THAT percentage(upper 3%) it really doesn’t matter what he  says as long as it’s “nice” and it’s personalised………The  bottom 97% ,you know the “regular guys” the email opener is probably not going to matter all that much anyway  because most women won’t even get to the “reading it” part after they see an “average” pic and have 78 more in their inbox to go through hoping to find a top 3 % guy. I’m sure a lot of times  the “half personalised/half form letter variant that I open with may come across a little robotic,it’s still my belief that if a woman like my pic,profile and stats she’ll return the email and if she doesn’t she won’t no matter what I say.

    For women it’s much easier because men(yes,even the top 3 %)get much fewer initial emails so basically as long as we find your profile attractive and you don’t open with “so what do you do for a living?” or “how come you don’t have kids?” you’ll probably get  a response.Conversely,if we don’t like your photo or it’s only from the neck up etc….(men are just like women)it really doesn’t matter what you say. For the most part women will not be disqualified for the many things men are,ie:height,education,income/job title etc….I do tend to shy away from women that have “3+ children in their profile though….lol I can do “2” but 4 is just too many…..LOL

  7. 7

    These are my favorites. The “I lost my ‘daddy’ to the rebels in the Sudan and I need a big strong man like you to save me” emails. This one’s fresh from my inbox:
    Hello my dearest,
    Hope this email finds you in good health with due respect and hearltful of tears since we have not known or meet ourselves. After i read your respond i can not hide any thing to you , i will like to open up mu mind and tell you about my condition here, Well I am Miss Amina Sary from republic of Sudan in Central Africa Dafur, the only daughter of Mr Almammy Sary. i am 26 years old lady .my Father was one of the high officers in the leadership of our country, was unlucky to be among those killed by the rebels army. but now i am presently in missionary church camp refugee in Dakar Senegal through the help of Revrened Sister who took me to this country senegal because of the on-going war in my country, which i lost my Daddy during the war i am the only dauther; left on the family, i am here with my age mother but it happen that my mummy died here last year on heart attach.even i lost contact of all members of my family as war scather everybody.
    There’s a lot more, but you get the idea.

  8. 8

    My biggest frustration is men (and to be fair I’m sure women do the same thing but they don’t write to me) who write an email of any type at all but fail to ask a single question.   They then finish by saying something along the lines of “looking forward to your reply” despite the fact that they have given you absolutely nothing that you can actually reply to.   I’m never sure if I should ignore these completely or if I should send them an email saying the following;

    “If you want a reply, you need to give me something to reply to.   Otherwise, a reply is not actually technically possible, leaving only the possibility of a “response” which is entirely different”.   

    Essentially, this type of email is the equivalent of a “wink”; it expresses interest but inherently requests that you pursue them.   I feel it’s like someone tapping you on the shoulder and then standing smiling silently, waiting for you to turn around and expecting you to strike up a conversation with them  when you do.   In reality you’d probably just look bewildered, ask if anything was the matter, then get on with whatever you were doing!?
    Spelling and grammar mistakes I can forgive.   This “oh hello, you look interesting.   Please strike up a conversation with me and we’ll take it from there” just annoys the hell out of me!

    What’s even worse is that I actually state on my profile that I’m looking for someone who is inquisitive; I get loads of emails from guys who write an essay about how they’re so inquisitive but who fail to ask a single thing!   I have started just pressing ctrl + f “?” every time I open an email, and if there are no question marks, I just don’t read it.   Does this bother anyone else?   

  9. 9

    I use the same approach with first emails as I do with first dates – give the guys a break. Not everyone out there is a Pulitzer prize winner. I will give almost everyone the benefit of the doubt and take a look at his profile, no matter how pathetic the email is, then try to word my reply based on the profile if the email gives me nothing to go on. (this is re: #8.)
    That said, the guy needs to at least try, and at least show that he has read what I worked so hard to write in my profile. So, “hey what up?”, “hey beautiful”, “your HOT!” and such will not get a response. Neither will a copy-paste email that is a detailed description of the guy, but says nothing about me. If you don’t want to put in any effort for me, I won’t put in any effort for you.
    @JB #6 – I actually wanted three kids, but my ex and I were so horrible as new parents (no communication, no teamwork) that we stopped at two… I wanted three kids really badly. Looks like I dodged a big one! LOL

  10. 10

    Sofka (#8):

    Not the same, but related: often you will see a woman’s profile that has something very bland, like this, freshly pulled from a random Match profile:

    Single attractive woman looking for the right man for the right reason(s) to be a friend and hopefully more. I am not high maintenance, I dont have to be spoiled, you dont have to go out of your way for me. You dont always have to know how to do things but in the end sometimes pretending that you know will get you a long way. I dont play games, I am genuine, real and highly dedicated to finding the right man for me. I am simple and real and very down to earth. If you want me to take notice then being your natural self and romantic will get my attention. Honesty is a turn on. I am looking for a man who is genuine and comfortable with himself. I don’t mind waiting forever for a genuine man if it means an entire lifetime then so be it I would rather wait for the right man then settle for anything less.

    Just like the e-mails you get with nothing to respond to, how is a guy supposed to  even initiate a message  to a profile like that?   She’s given  nothing at all, other than an opprotunity to take a look at her pics and send a “you’re hot” message.

  11. 11

    So bummed I am chiming in late, but how about the RUDE message?   I recently got a lecture from a guy letting me know that love isn’t all about looks, and just because he wasn’t tall and attractive, I should go out with him because he is nice.
    I nearly wrote back I wouldn’t go out with him because this was, by far, the rudest message I have ever received (based on the fact that he assumed from my profile I would not date him based on his looks).   Actually, I don’t like any emails that state “You probably won’t respond for such-and-such reason”.

  12. 12

    re Joe no 9

    Hmm, I’m interested that you see that paragraph as bland an that the woman in question has not given enough to prompt any questions. What type of thing would you consider to be non-bland, and is it more to do with content or with style?   Just an indication will do, if you don’t have an example to hand.  

    Personally, I can think of several conversation openers. Firstly, the termhighly dedicated to finding the right man for me” is quite an interesting (and also potentially humourous) one to me.   I might ask quite what form this dedication takes!? I suppose I find dating websites and peoples different approaches to using them quite fascinating in itself and I’d be keen to know about this woman’s opinions and experiences.   Or is she using other methods too and if so what?!

    Another interesting line: “You dont always have to know how to do things but in the end sometimes pretending that you know will get you a long way”.   I would ask if she had some specific situation in mind when she wrote this.   Otherwise, it’s quite a funny thing to say.   And compared with “I don’t play games, I am genuine, real..Honesty is a turn on” etc, you could have some fun!?   

    Also, you could start   conversation about how she would define the term “romantic” as it means different things to different people.   

    And while it’s good to ask things that relate to what someone has written about themself, you can ask things that don’t come from a person’s profile as well.   A question doesn’t need to be particularly inventive,just something like “if you could meet   anyone, who would it be?”.   It might not seem like the most exciting question ever when you ask it, but maybe the person you’re writing to has a really interesting answer.   I don’t really believe there’s such a thing as a boring question, only a boring answer.   And it just gives   the person the chance to show their personality and demonstrates that you want to know more about who they are.

    But then maybe you’re not much of a talker, and would rather be jumping off cliffs with your perfect woman? You would like more information about activity? If you can’t find anything about a profile that sparks your interest,   what would be your reason for writing at all?   We’re all looking for such different things.   My biggest gripe is the fact that I specify that I’m looking for someone curious and this is often just ignored or misunderstood.

  13. 13

    re Goldie # 9, I think you have the right approach, and I’d say I’m pretty open minded and open to giving people a break for most things too, but if a guy isn’t capable of starting a conversation, I really couldn’t see myself enjoying his company.   To be fair, this is probably my only must-have, other than kindness, not being more than 3 inches smaller than me (not logical, I know, but I’m   doing better than many women from what I’ve read on this site before), being in my age range and living somewhere near me.   

    I have grown up around men who have started every conversation by making a statement, and who see my role in the “exchange” as being that of commenting on their utterances and opinions.   I don’t want to spend more time with men like this.   I want someone who actively seeks to get to know who i actually am by asking me about myself and what I think, because, that at the end of the day, is what makes me who I am.

  14. 14

    What about people who immediately jump into questions that I’d assume would come later down the line?   So I recently got the “non-question” in the form of something like “I think we have a lot in common and I’d like to get to know you,” so it stumped me and I just said hello and “introduced” myself by name.

    So I’m expecting lighter get to know you questions or something about the things we supposedly have in common, but instead, right after “Hi, my name is…” I get “so when was your last relationship and why are you on Match?”   

    Both sounded really bizarre to me, and I’d never gotten that before.   I mean, isn’t everyone on something like Match to, oh, I don’t know, get Matched, and I think questions about previous relationships would not be your first question. I didn’t answer that.     

    I have gotten the blatantly sexual questions but those unfortunately are b/c of racist stereotypes and it’s of course a good screen and let’s me know immediately not to reply, although sometimes they send a decent opener and then leap into something offensive.  

  15. 15

    @ Sofka #13 – I agree with you about controlling men, or ones that believe a woman should know her place. However, it is impossible to make conclusions like that about a person based on their initial dating-site email. I have two teenage boys, had two BILs, have had many many male friends my whole life, and one thing I know pretty well about men is, with very few exceptions, they just aren’t good at writing letters. (why do you think guys like to text so much ;)) Moreover, a large portion of the guys that are good at writing an interesting first letter to someone they don’t know, are narcissists or players, or both. Or just guys who like the sound of their own voice and will later flood you with daily 2000-word emails. I’d say, if a guy is thoughtful enough to make a comment based on your profile, give him a chance. If he continues in the vein of “seeing your role in the ‘exchange’ as being that of commenting on their utterances and opinions”, then you can always cut him loose later.

  16. 16

    @Goldie #15 – I don’t actually see this “conversation format” as showing that these men as being controlling or that they “believe a woman should know her place”, apologies, maybe my explanation wasn’t particularly clear, rereading it I can see why you thought that!   All I think it indicates is that the man (or woman) in question has few social skills and doesn’t know how to engage someone in conversation or is simply too stupid to realise that just because someone does not volunteer their every thought and opinion, doesn’t mean to say they don’t have any.

    And while I agree that most men (or in actual fact, most people in general, I know plenty of women who fall into the same category, although thankfully I don’t have to date them too) aren’t great at writing emails, I don’t feel that I’m looking for some literary masterpiece. I just want evidence that a man is capable of starting a conversation.   If he can’t do it when he knows nothing about me and every question in the universe is yet to be asked, and when he has ample time to think about what to write (and to read the instructions and hints that most dating websites give), what’s our relationship going to be like twenty years down the line?

    Finally, I’m really rather intrigued as to why you think that good emails might be a sign of narcissim?!   For me,  they indicate that someone is intelligent, polite and considerate.   Of course there are always going to be intelligent “players” who are good at pretending they have all these attributes, but I find these people easy to weed out when their actions don’t match their words, and by and large, I don’t find players to be over represented among men that have basic social skills; if anything, the players I’ve met have been just as frustratingly lacking in the basics, with one or two notable exceptions!

  17. 17

    Just to add that in addition to ‘what not to say’ another turn-off before even getting through the entire contents of an email is someone who cannot spell, or  uses text language to convey a message in an email!

  18. 18

    Recently on a dating site a guy replied to my email. First off I had just sent a simple hello, I liked your profile, how are you type of thing, no more, no less. A two-liner. So I get this big, dramatic email back stating he had “found someone else” and wasn’t interested- something to that effect. I thought- Okay buddy, your ego is just a little too big there. I would have rather, in my opinion, for him to have ignored my email. I didn’t even know a thing about him. TMI_ too much information!

  19. 19

    I don’t understand why guys can’t just tell you up front they are not interested in proceeding on especially after weeks of constant texting and even talking on the phone but no offer to meet again they all of a sudden come to the realization they don’t want anything serious…WTF!!!   If you are not interested or even have the slightest hesitation just let us know and we can move on to someone who is.

  20. 20

    I sometimes get posts from men who, in their first message, ask about the weather, etc in Australia and then say they are thinking of resettling here and want to move in with me. Crikey! That speediness is frightening. It’s an instant and repulsive turn off. What can they be thinking, really? Do they actually imagine I’d welcome such a thing? Creepy? Heavens, yes.

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