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Online Dating: What to write when emailing someone you find attractive?

Yesterday evening I had an amusing telephone conversation with my good friend Bob (Let’s call him Bob because he’d never want me to reveal his true identity.)

A little background information; Bob’s a great guy, good friend, he’s smart, successful, good looking guy, knows how to treat a women and Bob has just started dating online with Match so isn’t too sure about this “online dating stuff” and is working out exactly what to do.

Last week he showed me his Match profile. I helped him re-write it and deleted some truly horrible online dating profile photos that he’d posted and replaced them with a great online dating photos.

Bob asked me what I thought about writing a great introduction email and then sending it off to a lot of women, to play the numbers game!

Quality over quantity.

I gave him this dating advice! “Most women want someone who is really into ‘them’, not the kind of guy who approaches every woman at the bar and NO woman ever wants to be sent a Form email “.
Personally I prefer to write individual emails to each woman. When it comes to online dating what’s important is the quality of communication rather than the quantity!

Last night Bob called me to tell me that he’d met a great woman online AND that she told him that 6 of her girlfriends and her (Who all live in the same small town) had all gone on together and would spend evenings with an bottle of wine, talking about the men they’d like to date.

Imagine if he’d sent the same email to all 7 women in the same small town…Do you think they would have noticed and  thought he was a douche-bag?

How to reach out to someone you find attractive online.

So what should you write when reaching out to someone that you find attractive online?

Writing a good email when reaching out to someone can be challenging because your words will be analyzed way more than normal.

I’ve written this post for men, but the advice applies equally to women.

1. Less is more.

When writing an email, remember that less is more;  give her the basics, elaborate later if asked;  You don’t need to give anyone your life story (and risk sounding like a narcissist) or ask a million questions (and risk sounding  like an interrogation.) Think about it, who is more intriguing? Someone who tells you their life story VS someone who talks a little and waits for encouragement to continue?
Make your first message at four sentences, maximum. Your first email is only an introduction- Don’t make her feel sorry that she opened your email.

2. Never be negative.

Never write anything negative in a dating email…simply stated leave out negative comments of any kind.

3. Tell her why you like her.

Tell her that you liked her profile, and why. For example, if a woman mentioned that she likes wine, let her know your favorite vintage. Ask her if she likes the local winery-this could be a great first step towards meeting her.

Don’t tell her how hot they look.

Even if you think that she is Angelina Jolie’s twin sister, don’t tell her how hot she is! Save compliments until after the ice has been broken. Establish a connection first and then your compliments will be more meaningful later.

5. Ask a question and make it easy for her to reply.

Take the time to read her profile. Notice the clues she/he gives you about what they likes, and he/she’s looking for. If she/he mentioned it in their profile… don’t ask again.

Ask a Question to get a reply…

And never beg for her phone number or even for her to write back. Remember just a simple introduction… and don’t spoil things by saying “If you don’t see anything you like, that’s fine too. Good Luck with your search!” Statements like this are HUGE turn-offs because they make her feel like you are expecting to be rejected.

Online Dating? Without a good profile photo no-one’s going to reply.

Having great online dating photos is the MOST important thing you can do when dating online, so visit LookBetterOnline and see how with great profile pictures we can help make your online dating experience successful and more fun than you thought possible!

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Comments (4)

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    Good info Giles, it’s good to get the male perspective! I agree with most of your advice. I think 4 sentences is too much though. Shorter is better.

    1. Introduce yourself
    2. Make a reference to one or two things in her profile that resonated with you
    3. Let her know you’d love to get to know her better

    And wait patiently…don’t write again, no reply = not interested!


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    Great and succinct advice! Will forward it to my single-n-looking friend 🙂


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    Agreed – sending out copy-and-paste form letters is a gigantic no-no!

    And don’t think you are “safe” from girls comparing notes, just because you live in a big city! In fact, I live in a very large city and I always talk to all my single girlfriends about the guys who approach us on-line. We are constantly comparing notes. It’s just what women do.

    On several occasions we have all received the exact same letters because the guys are all fishing in the same pond, it seems.

    It doesn’t exactly make a woman feel special…

    Another no-no is NOT reading her profile. It’s such a turn-off when it becomes clear that he has no idea that you love classical music and grew up in New England. I realize most guys only look at the pictures, but at least PRETEND to be interested in what she writes as well – or there will be no date.. !

    Oh, and make sure you have GREAT PICTURES. And ONLY great pictures! Gentlemen, we want to see your eyes and your smile. And up close, too. It’s so important!


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    I especially like the advice about asking simple questions, not only are you inviting a reply, you are also finding out more about her. Just remember to keep it simple and exude confidence.


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