Online dating is the greatest invention the world has ever seen. Think about it: it’s like online shopping for sex. You browse profiles, find someone you like and start a conversation. With any luck they will like you back and you can look forward to a new life of love, romance and passionate lovemaking.

In theory.

In reality, it’s like that game at the fun fair where you have to shoot a row of ducks but nobody ever seems to be able to hit the target. Fixed or not, it’s frustrating, and unless you’re a crack Marine Corps sniper, you will often go home empty handed. Online dating is a pain in the ass. As a “veteran” of over 60 internet dates and nearly 10 years of negotiating my way through the many, many websites out there, I know firsthand how arduous and frustrating it can be. I’ve made countless errors, put up stupid pictures, sent even stupider messages and had “sure things” vanish into thin air.

It’s this experience, however, that has enabled me to figure out what the hell I am doing, and I wish to share some of my tips and tricks with you. The following tips are for both men and women and they will hopefully spare you some of the failures that I went through.

1. It’s all about your main profile picture

Many online dating articles and products will try to convince you that what you write for your first message is the most important skill you will ever learn. This is true to a certain extent. For sure, what you write in your opening message and in your profile will dictate a lot of your success with online dating, but the single biggest factor is how someone responds to your profile picture.

It is the first thing they will ever see!

While your opening message’s content will determine if someone clicks through to your profile, it’s that little thumbnail image that will determine if they open the message at all. This isn’t a universal rule but take women as an examplethe more messages a woman receives each day, the pickier she is going to be. Have you ever deleted an opening message based solely on the thumbnail image? I think everyone has at some point, and imagine how often you would do this if you received 20-50 a day instead of 1 or 2 a week.

Now you get it.

Most attractive women don’t even open all of their messages simply because they can’t be bothered to sift through them all. You have to assume that a quick glance at the thumbnails is all she is going to use to decide whether to open the message, so if your main image isn’t the single best photo you own then you are doing yourself a disservice. No cheesy topless shots, no stuffy formal pictures and no Myspace style self-portraits either—you want a picture that shows you are a relaxed, fun person who has an active social life.

2. The key to writing an interesting profile

It almost doesn’t matter what information you write in your profile as long as you are conveying sincerity and vulnerability. The best way to demonstrate sincerity is to write your main bio in a loose conversational manner without trying to “big” yourself up. This isn’t a CV; you aren’t auditioning for anyone, so don’t write it like you are trying to impress. It will come across as needy, and although you may have the sexiest picture imaginable, your chances of meeting someone are virtually zero if you sound like a douche.

Vulnerability is the essence of opening yourself up without fearing rejection. Are you a geeky chess player? Are you passionate about computer programming? Do you have a fetish for licking stamps? Don’t be afraid of telling people who you are and what you love doing. A truly attractive person is comfortable in their own skin and has the confidence to reveal their thoughts and feelings without caring what anyone else thinks. Ask your best friend or someone you trust to proofread your profile to check that what you have written is a fair and honest representation of your personality and you aren’t coming across like a crazy person.

Unless you want to attract crazy people of course.

3. That all-important first message

Okay, you’ve sorted out your profile and taken some decent pictures, now you’re ready to send your very first message. What do you do?

First, don’t just send messages out blindly: you have to tailor the message to your goals and the person you are writing to. You don’t want to give a beautiful woman a physical compliment because it won’t have a huge effect on her. Likewise you don’t want to tease someone who comes across like they might not be the most confident person. With regards to messaging men, don’t be overly flirtatious as that can immediately set off their BS detector. Instead, give a man a non-sexual compliment and show interest in something from his profile. Guys, read that last sentence too—it applies both ways.

Common sense goes a long way here:

Read their profile.

Read it again.

Try to find something that most people may have missed. Does she love an obscure movie that you’ve also seen? Has he been to a country that you love? Is she doing a degree in a subject that you have knowledge about? Find something that you can grab hold of and use, whether that’s a specific piece of information or just a vibe you’re getting. Tailor your message around that. It’s hard to figure someone out based on just a few words and a picture or two, but you have to learn to go with your instincts. Unfortunately this will only come with practice, and the more messages you send, the better you will get.

Online dating is exactly the same as meeting someone the conventional way—it’s purely a numbers game and the quicker you realise this, the better. The more messages you send out, the more replies you will receive. Research has also shown that the best time to send a message is on a Sunday afternoon. That is the time when people are generally bored and are at their computers searching for a bit of companionship after their failed attempts at meeting someone the previous night.

4. How to get away from the internet and on that first date

There are two main ways to transition away from whatever dating site you are using: the first way is a slower process but it’s probably the safest option, while the second is very “high risk-high reward”, but is the quickest method if done correctly.

Option number 1

The slower method is about building trust and rapport. The best way to do this is to suggest moving away from the dating site to a more personal method of communication. Back in the day this was MSN Messenger, but nowadays you could use Facebook chat or WhatsApp. The advantage of Facebook is that you can get more insight into who they are, see more photos, find out the kind of circles they hang out in. It’s slightly stalkerish, but remember; they will get to see everything on your profile too so it’s a fair swap.

WhatsApp is basically an instant messaging service that is available on iPhone, Android and Windows and it involves trading each other’s phone number. From here you can send each other messages throughout the day and it’s a great way to have some fun. After you have built up a little more trust you can then transition to speaking on the phone—hey, you have each other’s number anyway so it makes sense.

Option number 2

You can skip all of this if you want and just go straight for the meet up. To do this effectively you have to use your common sense (I’m sure you have some) and suggest this at the right time. In my experience I would do this after maybe 20-30 emails back and forth. This may seem a lot, but if you are trading several emails a day then this should only take a week to accomplish.

The way that I bring this up is with a casual, “you seem pretty cool, we should meet up soon” comment. It’s very vague amd doesn’t pressure them into giving an immediate answer, yet it shows that your intention is to meet up, not to have a new pen pal. If the response is in any way positive, then go right ahead and suggest a provisional date, like saying “Cool, I am free on Monday to Wednesday evenings and maybe Sunday afternoon; let me know what is best for you”. Give a few options, such as different evenings, mix in a daytime option and sit back and wait. I would say 75% of the time you will get a definitive date set from this, but if not, then as long as you keep emailing each other, you can try again the following week.

Remember: as long as you keep chatting to each other, the interest is still there. Don’t feel discouraged by an initial “no”, as this could mean anything from feeling worried about meeting someone online to simply being busy with work. Keep building that rapport and don’t moan about it under any circumstances. Accept every decision and show that you understand. Be patient and respectful.

You can always revert back to option 1 at this point.

5. First date dos and don’ts

  • Choose the location yourself; preferably some place where you feel comfortable and that offers the opportunity to sit/walk side by side. Don’t go to dinner, the cinema or sit opposite each other—those promote a sense of detachment.
  • Act like it’s the second date already. Don’t start with an awkward hello and a million questions—chat like you would to a good friend.
  • Don’t offer to pay for a drink, just go ahead and do it. If they object, just tell them the next round is on them, (or next time if it’s only a quick meet).
  • The key to building rapport is to qualify and comfort. Listen intently and demonstrate an understanding or approval or what they are saying, then follow up with a similar story/example from your own life. For example: “I can’t believe you climbed Kilimanjaro, that is such a cool story—I’ve always wanted to do that but the closest I’ve got to that is a hike up Ben Nevis, which was cool in its own way because…”
  • Go ahead and talk about your online dating experiences—you can laugh about all of the crazy weird messages you each receive.
  • Don’t reveal how many people you have met up with if it’s more than 5 in a 1-year period, or if the person you are meeting is inexperienced at this.
  • If there has been some flirting and you feel that you have both enjoyed the date, don’t be afraid to go for the kiss. It is rare that you will receive a rejection and it demonstrates attractive qualities.
  • Use common sense, but don’t use fear as an excuse not to make the move.
  • Remember that you are not trying to sell yourself. Go in with the mindset that you are trying to find out if this person meets YOUR standards, not the other way round. Be friendly, flirty, funny and conversational without being needy.
  • Don’t ask for a second date—just state that you would like to see them again and you’ll be in touch soon to arrange something.

6. Finally, some important points to remember

You will have no doubt seen those tabloid internet dating horror stories, but they are so rare it’s not even worth worrying about. Meeting someone online is probably the safest method of dating. I say this because you have the option to check out everything about them before that first date, which is something you can’t do if you meet someone in a bar or club. If employers can use the internet to check out potential employees then you can do the same.

On a semi related note, make sure that the photos you have seen are genuine. If you can’t see their Facebook page or if their dating profile only has 1 photo then it is okay to ask to see a few more. I personally will never meet up with anyone if I haven’t had a good look at their photos. This isn’t being shallow at all, it’s simply reducing the chances of being conned into meeting someone who is 50 lbs heavier than their photo or is in any way trying to pass themselves off as better looking than they really are.

You can spot a fake profile a mile off; it’s really easy. If there is just 1 photo of someone with above average looks, little in the way of profile information, mentions sex in any way whatsoever, or uses their first and last name together then move on. It’s not worth the hassle. Similarly, guys: as you know, women don’t usually send out that first message so if you receive a message from a really hot woman and you feel uneasy about it, feel free to reply but beware—check those trigger signs I just mentioned and use your instincts and intuition.

Girls: you WILL receive messages from guys asking for sex. It happens, so it’s best that you’re aware of it from the outset. The majority of these guys are harmless and just lack social skills. The best way to deal with these is not to reply at all, not even a polite “no thanks”. Only reply to the guys that have put a little thought into the opening message.

So that’s it. Online dating is a bit scary if you have never done it before, but hopefully this guide (whilst covering the basics) is enough to get you started, and providing that you follow my advice about using your common sense and instincts, you’ll have a great time. Enjoy yourself and stay safe!

For those of you who feel stuck in the “dating rut” here are some ideas to get you thinking: 50 Date Ideas for Couples

Featured photo credit: sillhouette of sweet young couple in love standing in the field. Outdoor shot via Shutterstock

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