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Online Dating Blunders: Top 10 Mistakes Men Make When Contacting Women Online

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Here are the top ten things that you should avoid when contacting women online. This will be the most important online dating and relationship advice you'll read all year.

Mistake #1: Sending her 'just' a wink

Most Internet dating sites let you send “winks” or “show interest” for free, but what does this say to her about you? When that really hot girl gets your wink, she sees a guy that's not serious about wanting to contact her and too cheap to fork over the $20 membership fee. What a wonderful way to start off a relationship. Not!

She also knows that a wink is an easy “cop-out.” Anyone can scroll through hundreds of online profiles and wink at everything that moves. From her perspective, why should she spend time on you when there are dozens of guys taking the time to send her real messages every day?

Mistake #2: Not having a recent quality photo in your profile

This one should be easy, but the fact is, most men do not upload their photo. The statistics on this one are very clear. Profiles with photos get 10 times more looks than those without; and profiles with quality photos get four times more than profiles with poor photos.

Let me ask you: When you log on to a dating site and search, don't you search for women with photos in their profile first? Why would she be any different? Many women will assume you have something to hide if you won't post your photo – like maybe your wife.

If you don't like your photo, have one made professionally. There are many professional photo services that do nothing but create great photos for your online dating profile. If you want to stand a chance against the other guys out there, upload a good quality photo.

Make sure you upload a recent photo. Nothing is more disappointing than to meet someone and realize the picture they sent you was 20 years and 40 pounds ago!

Mistake #3: Sending a message with a boring subject

Fact #1: Guys outnumber girls by at least two to one on most online dating sites, and that's a conservative number.

Fact #2: Good looking girls get dozens of winks and messages in any given day. You can have the most awesome profile and you can send her the most intriguing message, but she may never see it. How come? Simple; once again, women with good online profiles get lots of winks and messages every day. Give her a reason to open your message first! It has to stand out among all the others or it has a high chance of getting deleted and never read.

Spend just as much time crafting an intriguing subject line as you do in writing the rest of your message. Ask her a question or specifically reference some detail in her profile so that she will know you actually read it and are truly interested in more than just her looks.

Mistake #4: Sending her a vague, generic or otherwise lame message

You made the effort to become a paying member of a dating site and want to make the most of your membership, but then you came up with a standard boilerplate message and you quickly copied and pasted it to dozens of girls.

Go you! At least that's what you think. Okay, reality check.

Women like to feel special and important. They can smell a lame form message a mile away, and the delete button is always close at hand. Why not take a different approach? Actually read her entire profile (we know it's painful, but do it anyway), learn everything you can about her, and then send her an insightful, personal message.

About Dan and Jennifer

  • sehpferd

    Dear Dan and Jennifer,

    your advice is excellent – I love item 10 of your list – it should really be on top of the list, because it is the first thing you should know when you start dating.

    Best wishes

    Gebhard Roese


  • Single Asian Woman

    I have to say that your articles are worth reading. At first, I thought I’ve read everything I need to know about dating, relationship etc. but after I’ve looked at your site, I’ve just realized how much more I need to know!

    Keep up the great work and expect me to keep coming back to read your latest blog.


  • Jaison Williams

    I will say women are all about connecting with their minds. Just because you’re looking for a quick fling, that doesn’t mean she’s going to respond.

  • Dating Advice For Men

    I really need to emphasize more about the profile pictures. It is best to add more than 1 pictures. Seriously, people will find more of your pictures. Be it with your friends, teachers, family etc.

    For me, if you show more pictures of yourself plus pictures with other people with proper caption/tags, that might bring you and her closer as she know what kind of friends and family you have.

  • Singleman

    Mistakes 1, 2, and 3 in particular stood out to me. Forget about the winks and flirts and crap like that. Send an actual MESSAGE!

    A recent photo is rule #1. You must look the same in person as you do online.

    A lot of people say something lame in the subject – like Hi or Hello or something like that. Too much competition out there. Gotta do everything possible to stand out, and the subject line is a great start.

    Great article overall.