Posts Tagged With: online dating

Online Dating – Part Three



Hello, and thanks for visiting my blog today! We conclude this three-part discussion on online dating, where we focus on meeting your match in person. Hopefully, you’ve connected with someone online, exchanged messages back and forth, so now it’s time to go from online to offline. If you haven’t connected with someone yet, no worries. Don’t give up because you are bound to connect with someone, assuming you’ve been putting effort into your initial messages.

And now back to asking that match for a date. Yes, it might seem nerve-racking, but at some point you want to meet that someone you’ve been seeing online in person. Nobody joins a dating site for pen pals, and let’s face it having a pen pal is not going to establish a serious relationship. And just as us guys make the first move in messaging, we’re the ones that ask the girl out (sounds familiar, huh?). While you might be hesitant about meeting a total stranger in person, taking things offline is important for several reasons:

  1. It’s the only way to know if there’s real chemistry. You and her might have great online chemistry, but offline it could be a different story. In fact, you might find that she is not the person you thought you met online. Best to find out sooner rather than later. And at least if it doesn’t work out, you haven’t wasted a lot of time or mental energy.
  2. You are not the only one she is messaging. You can be sure that she is messaging several other guys – and possibly has set up dates with them too. You’ll want to find out there is a potential future with her fast, otherwise someone else will take your place.
  3. It shows you are serious about a relationship. Women don’t like men who play games, and if you hesitate to meet in person she will think you are not serious and move on to another guy.

When should you ask her to meet in person? It depends on the person and the flow of the online conversation. By the time you ask her out, you should know the following about each other:

  • name
  • occupation
  • hometown
  • a little bit about family
  • hobbies

In my experience, I think after five mutual messages it’s safe to take things offline. If you are thinking in days, assuming you have been exchanging messages on a daily basis, I would say go ahead and ask her out after day four. Not sure how to ask her? Try this:

Hey, I’ve really enjoyed getting to know you, and I’m very curious to know what you are like in person. I was wondering if you would like to meet for coffee soon? We could exchange numbers in the meantime. If you’re not ready for this yet, I understand.

This example can’t go wrong. You make the offer, yet acknowledge if she’s not ready to meet you. The worst that can happen is she simply say she’s not ready – yet. Speaking of women not being ready, some women may, in fact, not be as eager to take things offline as you are. Respect this. In this case, just continue to exchange emails. After a week or so, you can ask her out again. Hopefully, by then she’ll say yes. It’s okay if it takes a couple of weeks before you finally meet.

people, lifestyle and dating concept - happy couple drinking cof

So where should you meet for the first time? Some sources will suggest you go all out and have a date filled with multiple activities. Since you’re trying to see if there’s authentic chemistry, a coffee date is the best bet. It’s a public place, relatively quiet, and comfortable, allowing the two of you to get to know each other. It’s just coffee, and if you find there’s no chemistry, you can simply go your separate ways afterwards. When selecting a coffee shop, try and come to a mutual agreement. If she’s like, “I don’t care, you pick,” choose a Mom & Pop type place. Try using Yelp to find the best place, but make sure that it is one that the both of you can easily access and has parking.

Don’t like the idea of coffee? You could go to a bar and have a drink. Just keep the booze to a minimum (for obvious reasons).

Places you SHOULD NOT choose for the first date/meeting:

  • your place, or hers
  • movie theaters (save that for the second, or third date)
  • nightclubs, or any place that’s too dark or loud
  • restaurants (too much potential for disaster, especially when you haven’t met in person yet)

What day is best for the first date? Some sources will tell you to avoid Fridays, Saturdays and Mondays. To be honest, the day of the week makes little difference in whether you’ll have a great time and/or true chemistry. You should choose a day that is good for BOTH OF YOU! And give each other options. Just because you’re free on Sunday, doesn’t mean she is.


What should I wear?
No need for a tux! Just wear something casual, but definitely no lounge wear! Make sure you are cleanly shaven, comb your hair and brush your teeth. Chew on some mint gum half an hour before the date! And ladies, leave the heels at home. Comfortable shoes are a must!

What should we talk about?
Find out more about what you’ve been talking about online. Ask open-ended questions, and avoid the following subjects: politics, exes, religion, and sex.

What if there is true chemistry?
Ask her on a second date, silly! Better yet, take her to another venue such as a comedy club or a walk in the park.

The date was great, but I’m not sure if there is potential. What should I do?
Take some time for thoughts and reflection. It is common for people to be unsure of whether they should see each other again. After a day or two, you will have a better idea. You can either go on a second date, or simply tell her the truth. If you do decide to tell her the truth, do it soon and try and do it over the phone (no texting).

What if I know right away there’s no potential?
You can either ride it out, and mutually part ways after, or lie and say you forgot that you promised to help out a friend (careful with this one since lies end up catching you in the butt). It’s best to be honest in person and end things so as you don’t waste your time – or hers!

Well that wraps up this adventure of online dating. I hope you have learned something from this, and I wish you happy dating! Until next time!

Categories: Life | Tags: , , , , ,

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!

Categories: Life | Tags: , , ,

Online Dating – Part One



The holidays are over, kids are back in school, and people are back to work. All the Christmas related inventory in retail is now replaced with pink/red hearts and chocolate. Which means it time to start thinking about Valentines Day.  Some of you have found yourselves suddenly single for whatever reason (I find January sees a rise in the number of newly singles). With that, you’ve likely put yourself on the online dating market – or at least contemplating it. Having been on a couple of dating sites in the past, I would like to help you get your profile set up, and avoid the mistakes that many online daters sadly make.

Before we go into what I would like to share, I should point out that I am not going to recommend certain dating sites (Match, Tinder, etc.). I don’t want end up in legal trouble. Besides, you could find out more by doing a Google search. I will, however, you suggest that you set up a profile on two sites. One that is free, and one that requires a monthly fee. The reason for this is so you can cast a wider net, and have more options. In this post we will focus on two things: how to articulate yourself online and your profile photos.

About Me

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Most dating sites feature an About Me. This along with your photos are the make-or-break for your profile. They will decide whether a potential interest will view or pass on your profile. Think of this as your resume. Employers will glance at a resume for a few seconds before deciding to read on or dismiss. Potential love interests do the same. In the About Me, you are basically providing an abstract about yourself . Some sites have no word count limit, but you should aim for 250 to 300 words. A lot of users, especially first-time users, make the mistake of describing themselves with generic adjectives. I’ll use an example from a profile I came across while using a dating website:

I’m kind, caring, intelligent, and generally unintentionally witty.

This basically says nothing about yourself. My reaction was, “Okay…so?” It is way better to describe yourself in detail such as where you are from, what you do for a living, your personality and what you like to do in your spare time. However, you also want to add something unique about your hometown, job, personality, etc. This way you’ll stand out from the competition. An example could look like this:

I’m from a Toronto suburb that is known for being in the gridlock of rush hour traffic. I’m a teacher, and I love the fact that I’m helping people achieve their goals. I don’t mind being the topic of ridicule, say when I make an awkward classroom entrance. I asked my friends and family to describe me, and two words that kept coming up were loyal and adventurous. So…I’m basically a talking cat possessed by the spirit of Indiana Jones?

This example shows rather than tells, and it also incorporates humor. And speaking of humor, your profile should have a mix of seriousness and humor. It is a much better way of saying, “I’m funny”, which is another common error made in online dating. An example like the above will likely entice a user to message you, or reply to your message (More on messaging later).

More tips on About Me:

  • it should include something about your personality, hobbies, and life growing up
  • as previously mentioned, humor is key
  • don’t go into too much detail about your job. Some sites have a section in which you describe what you do for a living; save it for that. Otherwise, just briefly explain your job and why you are passionate about it
  • avoid adjectives like the you-know-what
  • No using platitudes. A common example could be, “That’s a loaded question”. Again they say nothing, and make you appear like you could not care less about online dating
  • describe what kind of partner you are looking for, and not just the physical necessities. Example could be: I’d love to find someone that embodies the words active, adventure, caring, and doesn’t mind the occasional tickle fight.

Some sites do not require users to fill in an About Me section, and as a result some users do not even fill this out. I’ve come across such examples during my online dating days. DO NOT DO THIS! This is a surefire way to have potential matches skip your profile.


The next most important part of your dating profile. Actually, it is probably THE most important. You know the old saying, “Don’t judge a book by its cover.” Well, not when it comes to online dating! Good photos make potential matches want to read your profile; bad ones send them on to the next profile. It is crucial that your profile photos are the best pics you’ve got! You would be surprised how many users get this one wrong. You may have a well crafted profile, but unless your photos are good quality, other users will pass you by. So here are a few Dos and Don’ts when it comes to photos.


  • have photos that show you from the torso up
  • have a friend take a few photos of you, say in your garden of you leaning against a tree and smiling
  • have at least one photo of you engaging in your hobby
  • one photo of you with a friend, or several friends (to show you have a social life)
  • post recent photos of yourself. Nothing older than two years
  • definitely post a picture of you from a recent vacation


  • bathroom selfies or selfies of any kind. I can’t tell you how many I came across in online dating, and it immediately turns me off. These just make matches think you couldn’t be bothered into putting effort into your photos
  • accessories. I’m talking about photos with you wearing sunglasses, hats or anything else that obscures your face. Matches want to see your entire face, and anything that blocks it will make a bad impression
  • photos of you with an attractive friend or relative. It makes the user think, “Gee, her friend is cute, I wish I could message her.”
  • photos of you with Instagram filters (you with bunny ears or cat whiskers). It’s okay for Instagram, but not for online dating
  • photos of your pets without you in the picture, or of you with your back facing the camera. You’d be surprised how often this happens!

Another common photo mistake is the user posting all group photos, in other words all the photos contain them with other people. Don’t do this! This makes me think, “Who am I messaging?”

How many photos should you have? Ideally, four to five is great! They should be of you only, you with a friend, and you pursuing your hobbies/interests. It is important to note that your main photo (the one other users first see) should be of you alone, looking your best. Here is an example:

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This does not mean you have to do a photo shoot. Just simply have a friend, or relative take a few good shots of you. That’s it! Again, I want you to learn from mistakes I’ve made and seen.

Stayed tuned next week, as I will talk about messaging a potential match. Until then, happy online dating!

Categories: Life | Tags: , , , , , , ,

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