Online Dating – Part Two



So last week I talked about the basics for setting up your online dating profile. This week, we move onto messaging. You’ve set up a profile, browsed potential available matches, and one – or several – has caught your eye, which means it’s time to break the ice and send an introductory message.

Messaging is the part that many male users mess up. That is, they send one-liners, sexual innuendos and anything else that makes a woman roll her eyes and ultimately hit ‘DELETE’. Such bad messages include the following:

  • “Hey!”
  • “What’s up?”
  • “Hey cutie!”
  • “I like your profile.”

Internet dating

These messages are surefire ways to end up in the trash and make a bad impression. You would be surprised how often women receive messages like these. In fact, they get so many they decide to delete their accounts.

Women are flooded with messages, so it’s important that you make yours stand out from the crowd. You have only one shot to make a good impression, so make it count!

Keys to sending an impressive first message:

  • read a woman’s profile entirely before messaging. Women have taken the time to write out a well-crafted profile, and in return expect us males to read through their profile
  • Comment on something that caught your eye from their profile (one of their photos, hobby, philosophy, etc)
  • don’t introduce yourself, in other words don’t say, “Hi! I’m…” Save name exchanges for the second message (assuming she replies to your initial message)
  • don’t comment on her looks, or username, or otherwise put her on a pedestal. Chances are she’ll have received plenty of messages commenting on those. Remember, stand out from the crowd!
  • if she happens to be online at the time you are messaging her, DO NOT say, “Hey!” You might think this is a great way to start a conversation, but this rarely works. It’s best to message her as if she’s offline
  • your initial message should be one to four sentences. No need for a paragraph!
  • Definitely ask her a question. This increases the chances of her replying

The time you message is also key. In other words, you should not send your first message to her on a weekend night. Women will assume you have no friends and/or drunk. Best to message at other times. I find Saturday and Sunday mornings are great!

Not sure what a message should look like? Let’s take a woman with a picture of her with the backdrop of the Tower Bridge in London. She says she’s from Atlanta and hopes to own a ski chalet in Colorado someday. You could message her like so:

I’ve been to London myself! It’s an amazing city! Did you go up the London Eye while you were there? What brought you here from Atlanta? 

P.S. Those are cute flip-flops you are wearing in that photo!

See how this shows interest in a match? This person has clearly read the profile, and not just Women also love it when you comment on their accessories like shoes. Don’t worry if you haven’t actually been to London. You could tell her you would like to go there, and ask what she liked the most about it. You could also ask her questions about her dream ski chalet.

Now I want to talk to you ladies for a moment. I know that it’s us guys that make the first move, but many women make the mistake of waiting for Prince Charming to appear out of nowhere. You want to be proactive when searching for online matches. You should be sending out initial messages, following the same suggestions I have already pointed out. Many women complain that they only get creepy messages when in fact they haven’t sent out a single introductory message. By taking the first step, you increase the odds of connecting with someone special. Don’t be afraid to send a few messages!

Waiting for a reply

So you’ve sent the first impression, and now you play the waiting game. First of all, good for you for taking the first step! (Exhale). What happens next? In my experience, a woman who is truly interested in you will reply within 48 hours. Having said that, if you don’t receive a response within that time, she’s likely not interested. No biggie, just move on. Active online daters have dating apps on their phone, so you can be assured that they are checking their messages.

You shouldn’t message one match,  and then twiddle your thumbs hoping for a response. Successful online daters search and email, search and email. They don’t put their eggs in one basket, and neither should you! The more thoughtful messages you fire out, the more likely you are to make meaningful connection.

Why didn’t she reply?
Most of the reasons are those beyond your control. You can craft an amazing profile, but it will not impress every woman. She probably doesn’t like your taste of music, food, or it could be because you are either too tall or short for her. Women are also intuitive and maybe something is telling them you aren’t right for them. On the other hand, she’s probably too busy to reply at the moment, become serious with someone else, or is fed up with creepy messages and ready to commit online dating suicide. Whatever the reason, she might not be the right match for you anyway.

Should I send a second message?
So you want to send a follow up message to someone you already messaged (Hey, did you get my message?). I find that follow messages don’t work. If she doesn’t reply to your initial message, it’s best to leave it at that and move on. Now I’ve heard of stories of men extending the fangs and bombarding women with follow up messages, hoping for a response. If you do this, she will respond by either blocking you or reporting you. Remember it’s very easy for us men to come off as creeps when it comes to online dating. Don’t become a creep!

Shouldn’t she be honest and tell you the truth?
You’d think! Women are not obligated to reply, and frankly they know that by replying will just open a can of you-know-what. Just accept the awkward silence as “thanks but no thanks!”

You Get a Reply

Awesome! Especially, as reply rates for men are pretty low. So you’ve gotten a reply, which opens the door to online chatting. The key to this is to get to know each other as best as you can before meeting in person. Find out about her family, job, hobbies, places she’s been to, etc. Every message you send should end with a question.

Now I want to warn you about a couple of negative messaging scenarios:

  1. Mediocre replies. An example is when a match simply replies to a question you asked, but does not ask you anything. Matches like these are not likely interested in you, and are just being polite. I’ve found that engaging in conversations with these types is likely to fail, and should be set aside. In other words, treat them as ‘fail to reply’.
  2. Vanishing act. This happens where you are having a great online conversation, and all of a sudden they stop replying. It happens, it blows, and unfortunately there’s nothing you can do about it. You can try to revive the conversation, but I’ve found that once they stop replying, they…stop replying!

So I hope this post has been insightful. Tune in next week for how to go from online to offline!

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