How To Approach A Woman Online – From A Woman’s Perspective

Before I was married I experienced my fair share of online dating, including many e-mails from potential suitors online. I really did get to see the good, the bad and the ugly. And I have chatted with many of my girlfriends about their experiences of online dating. This article summarizes what works well for a first e-mail to a woman and what makes our blood run cold and our hands hit DELETE before the end of the paragraph!

  • Do be friendly – It sounds obvious and you would be surprised how many men forget this when they send their opening e-mail. It’s as though the logical masculine part of the brain takes over and they want to get right to business (talking on the phone/dating or even sex). Unfortunately we women don’t work that way. We like to dip our toe in and see how we feel with you first. We like to be romanced and experience friendly conversation and attention from you. Think of it as ‘warming us up’ if you like. Always open with a friendly, conversational e-mail (not too long) and you will get many more responses.
  • Do keep it light and interesting – There is a balance between interesting/attention grabbing and off the wall/off-putting. I know that it can feel like pressure when you are trying to write a good opening e-mail. The best advice I can give is to be yourself. Read the section below on how to avoid being boring and here are a couple of tips for you to help you present yourself as interesting and let her know you are worth replying to. Read her profile carefully and comment on something you find there. Relate it back to something you have experienced if possible to create a connection. Compliments work well provided they are not overdone and are genuine. One small compliment is nice for a first e-mail. You can also talk about something that has happened to you in your day, something that shows a bit of who you are. If you are a funny guy feel free to use a little humour, just don’t overdo it. Dry humour can easily be misconstrued via e-mail. Women connect through emotions and shared experiences, and if you can create a connection with her you are half way there.
  • Do keep it short – Although we want you to be friendly and fun we don’t want an essay. A whole page of writing will likely send us to sleep if we read it at all, however riveting it might be. At best we may skim read it and we will be judgemental and wonder if you are self obsessed when we open the e-mail to see a whole page of writing!  Your e-mail needs to be accessible and easy for us to read, which means short and attention grabbing. Go for quality over quantity. A few short and impactful paragraphs and a compliment is a recipe for success.
  • Don’t be boring – OK I realize it can be hard to know what to say, so I am going to give you a couple of quick hints. Boring is writing a list of stuff about yourself such as your traits, or sending a message which just asks her whether she is up for talking with no other information. If she doesn’t get a feel for your personality from your e-mail she won’t know whether she wants to talk to you. And so she will just not bother to reply. You want her to feel compelled to write back. Don’t just rewrite your profile, she will read that if she is interested.
  • Don’t be cheesy – Many men will overcompensate and try too hard. This can look like over-use of compliments and/or humour, and always comes off at best as cheesy, and at worst as desperate. Write to her as though you were talking to a female friend, that will prevent you from being too formal and falling into the mind set of trying hard to impress her. Use humour and compliments but sparingly. Just like salt makes food better it is only good when used sparingly, the same principle applies here.
  • Don’t list all your requirements – Sometimes men will list all the things they are looking for in a woman in that first e-mail. And sometimes they will list all the traits that they don’t want (even worse – cringe!) This comes off as rigid and will turn a woman cold. She is unlikely to reply if you do this.
  • Don’t slag off other women you have met online – Sadly this too was common in my online dating days, and it always turned me cold. It is very uncomfortable for a woman to listen to a man slagging off another woman he has dated. In the back of our minds we are wondering if we will share the same fate as her and it makes us feel on tenderhooks wondering if you are being as judgemental of us as you were of here. Avoid this like the plague.
  • Don’t talk sex in the first e-mail! – I understand that when you find a woman attractive you think physical, and there is nothing wrong with this. However we women are very sensitive about being approached purely for sex. For most women who use an online dating site, this is not a primary reason we are there, we are looking for dating and/or a life partner. I know the same is true for the vast majority of men who are on the dating site too, and unfortunately there are also many men who are just there because they want to get laid. And our radars are sensitively tuned to detect those men. We will screen them out very quickly, so avoid being labelled as one of ‘those men’. Avoid mentioning anything sexual in your first e-mails. I do know that there is advice out there from male ‘pick up artists’ which talks about building escalation and sexual tension, and this  is all well and good, however in my opinion it doesn’t work for online dating. At least it only works when done a certain way. Fun flirting is excellent, but you won’t make it too that stage if you have come across too sexual in your first communications. To us women it is crass. It feels like a shortcut and we believe we are one of the masses you are trying this approach on. Remember, she wants to feel special. Work on a connection first, then some gentle flirting.
  • Above all get your mind set right – She may be heavenly, and remember she is just one woman out of many. If you are having problems connecting with women online and getting replies to your messages, look at your mind set first. Are you feeling desperate? Do you put all your hopes into one e-mail when you send it? If so this will come across in the e-mail and will put women off. Work on your own confidence and mind set so that you know there are many options for you. Your dates will come and the outcome of any 1 e-mail is not important. This will have you able to send fun, engaging and light hearted messages that will get a good response.

Have fun!


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