Don’t you just love modern day technology. So many ways to connect and meet women but also so many ways to screw up in a matter of seconds.

To help combat these issues, I have put together a quick list of do’s and don’ts for online dating. These rules can also be tweaked to applied to other areas like emailing and texting.

Print these rules out and put them by computer and read them every time before you engage in online dating!!!

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Online Dating Guide: 14 Dos and Don’ts of that First Crucial Email

Written by: Jennae

Online dating often feels like its own world. Real winks are replaced with virtual ones, and chemistry is guessed at through pictures and profiles. But the biggest difference between online dating and meeting someone in the real world is how much words count, specifically, written words.

A lot of men fail when it comes to online dating because they don’t give good email 😉

Yes, it’s that important. In a virtual dating word, your written words are you. It’s not only important what you write, but how you write it.

DON’T wink. Yeah, yeah, it’s a nice little tool that helps you figure out if someone is interested in you or not, but what it really says to a woman is “I’m too shy to actually talk to you.” And while shy can seem endearing, most women doing online dating have a ton of men contacting them, especially if they are someone worth contacting. You winking at her isn’t going to stand out as much as a well written introductory email.

DO keep it light. Funny is sexy! While writing a joke is harder than telling one, any bit of humor you can put in your email is a good way to show off your personality. And women like men who make them laugh.

DON’T use IM/text speak. I will tell you right now that I delete anyone who contacts me with “How R U doing 2day?”If you can’t take the time to actually spell out your words, you’re just not worth mine. Women want men who can hold actual conversations, and writing like you only have 140 characters isn’t the way to convince them of that.

DO keep it short. Too long of an email tends to give a bit of the creepy vibe, and no woman wants to read a novel about why you decided to write to her: “we have this in common, and this in common, and I think you’d really like my mom!” But while short is good, too short can also be an issue if there is nothing for her to respond to. Aim for around three lines, minimum, but no longer than a couple of short paragraphs.

DON’T forget to spell check and edit your email. If the online dating program you have use doesn’t have a built in spell check program, write the email in Word or the equivalent and copy and paste it into the body of the email. Appearance counts, and just like you wouldn’t try to pick up a woman in a bar wearing sweats and a dirty t-shirt, you shouldn’t try to pick up a woman online half-assed either.



DO read her profile and make a comment about something you read. This comment shouldn’t be “I can’t live without sex either, so why don’t we get together and save each other’s lives?” It should be more like “I really like hiking too. What are your favorite spots?”

DON’T give out your contact information right away. Any guy who sends his phone number or even AIM or other messenger services contact information to me in a first email I automatically label as a “player”, someone not interested in any sort of long term relationship. It’s sort of like walking up to a woman and handing her your card first and then trying to have a conversation with her after. It might work in a business setting, but not in a romantic encounter.

DO ask at least one question, preferably about something you read in her profile. This proves you actually read her profile and didn’t just check out her picture, and that, again, you’re capable of having a conversation. However, first rule dates apply to first emails as well, and this question shouldn’t delve into heavy topics like past relationships or the reason why she’s doing online dating. But by asking a question you give her something to respond to should she decide to write back to you.

DON’T start talking about sex right away or compliment her in a sexual manner. Women like compliments, but “you’re very pretty” is different than “I can totally see myself having sex with you.” Also stay away from complimenting particular body parts that are not eyes or smiles.

DO sign off with your actual name. The screen names are entertaining and all, but signing off as “drlovegod137” isn’t going to personalize you to the woman you’re contacting as much as “Jim.” Remember, you want to get her thinking of you as a person and not just a profile.

DON’T come on too strong or immediately suggest getting together for coffee or a drink. Women like to be wooed, and that’s a two-email minimum of you asking questions about herself and answering questions about yourself, slowly establishing that preliminary trust that will make her feel comfortable meeting with you. However…

DO communicate clearly. Ambiguity is not your friend in email, where it’s hard enough to read someone’s tone as it is. If you’re making a movie reference or a joke, make sure she can tell that’s what it is and not a really bad pick up line, especially if the joke is in reference to something in her profile. You might think you’re being clever, but she might not remember that she talked about the Simpsons, so why are you talking about the windmill in a mini golf course?

DON’T wait longer than a few weeks of email exchanges to ask a woman to meet you. The point of online dating to is get offline and actually meet to see if the chemistry is there before getting too invested. I’m perfectly fine with a man suggesting a meet up after about two or three email exchanges, depending on how much we actually talk about it those emails.

DO follow up. Now, assuming you’ve done your job and paid attention to her profile, writing a well formed email with proper spelling and grammar, at least one attempt at humor and one question, it’s up to her to decide if, and when, she writes you back. If she does, the follow up email should follow the same advice as the first with the exception that it’s allowed to be a little longer—a little longer. This is not your opportunity to write a thesis paper on why Kobe is the best basketball player ever or how the iPhone has changed your life. This is where you answer any questions she asked, and then ask her a few more of your own. A good rule of thumb on email length is to respond about the same length she’s written to you—mirroring behavior works, even with emails.

Remember, your email is supposed to show the woman in question that you’re good at communicating. Think about how many fights between men and women are about a lack of communication—you don’t want that to be you. Giving good email is the best way to get to that first date, but after that first date remember that nothing speaks as loud…as your own voice. Picking up the phone is always a good idea.

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