10 Tips for Successful Online Dating

When many people think of online dating, they think of all the World of Warcraft addicts and goth kids from high school getting together online trying to get dates. I actually felt the same way about it until I undertook a research project a year and a half ago that led me to join 18 different dating sites, going on a date with a girl from each one. I was doing research for a dating service branding project, but I took away two things I didn’t expect: first, that online dating sites (depending on which ones you join) are actual full of great people who are looking for an alternative to clubs and bars for meeting new people, and second that there are some oft-overlooked tricks to online dating that, according to many of the conversations I had, most people are not using.

Here are ten of those tricks. Make use of them, and you (and your date) should have a much more pleasant experience (and maybe you’ll find the girl or guy or transgendered person you’ve been looking for)!

1. Be Yourself

I cannot stress this first point enough. Do not, I repeat, DO NOT pretend to be something you are not while online dating. Not only will this lead to inevitable disappointment for your date, it will also end with inevitable embarrassment on your part when your date walks out on you, comments on how much weight you’ve gained or hair you’ve lost since you took the photo on the site, or asks you where the tattoo went (this is an actual story I was told..apparently a guy that the storyteller went on a date with had Photoshopped a tattoo onto his arm in order to strike up a conversation with the girl, who liked tattoos…she was not amused when she found out).

If you are convinced that you have to lie in order to get someone to go out with you, I strongly disagree with you. Using the Internet, you can take what you have and find someone who is looking for exactly that. That’s the beauty of a network that knows no boundaries…unlimited options for everyone. And if you find that the people YOU like are out of your league, well then start running laps and learning a new language, because online dating with not help you fake out someone for long, buddy.

2. Answers the Questions

It’s amazing how many people will complain that they’ve had no luck with online dating and then I’ll take a look at their profile and there won’t be any pictures and most of the fields aren’t filled out. “I don’t want my picture up on a dating site,” they say. I just sigh. There’s no way you’re going to find great people to date online if you don’t have enough commitment to post at least one picture and fill out 90% of the fields on your profile page. Would you go out on a blind date with someone from the Internet, sight unseen? I wouldn’t, and I doubt you would either. So even if you want to come back to them later and put in something REALLY good (see Tip 3), fill out all of the fields, upload some of your Facebook photos and stop whining, because otherwise you’re standing in the doorway and complaining that you don’t like the house.

3. Brand Yourself

As with any social environment, the first thing someone notices about you is what you can display from across the room. In the real world, this usually amounts to how you dress, how you style your hair, how polished your shoes are, etc. In the wonderful world of online dating, however, you have myriad different levels of information you can display. This means you have a lot of opportunities to shine, but also a whole lot of opportunities to foul up big time.

Starting out, know what image you are trying to get across and what story you want to tell. Put yourself in the shoes of someone who is visiting your profile. Say you want to come across as sweet, but with a sexy side. Is that coming across? If not, balance your photos a bit better (have some that show you being sweet, some that show you being sexy, with the balance being about what your personal sweet:sexy ratio is), insert a few more salacious comments among the cute ones, and check it out again. Have a friend check it out, if you’re feeling extra brave. Ask them if it represents you well, and if not, what they think you should be emphasizing more.

4. Don’t Be a Creepster/Lurker/Troll

There are certain civilities that are usually followed on online dating sites that you would be wise to uphold (this mostly applies to guys, but girls can be guilty of them, too). Firstly, don’t be that creepy guy who sends awkwardly sexual messages to girls half your age, writes intentionally offensive things in the forums or harasses other members. It’s simply not cool, gives online dating a bad name, and will likely get you reported and booted from the site. Secondly, most sites allow some kind of opt-in or opt-out functionality that allows people to see who has been viewing their profile. If you’ve been back to the same person’s page 10 times today, it’s time to send him/her a message, otherwise you might become known as a ‘lurker,’ essentially the Peeping Tom of the online dating world, who is basically there to look at other people’s profiles and do god-knows-what while looking at them. Not a good reputation to have. Thirdly, if someone sends a message to you, it’s usually good form to send them something back. Now, if their message to you is at all off-putting (sexually-charged, offensive, too short to glean anything from, etc), then just delete it and go on with your day. If they took some time to form whole sentences and strike up a conversation with you, however, even if you’re not interested it’s polite to jot down a quick reply and either respond to them in a way that encourages more communication or in a way that cuts the convo off (nicely).

This, of course, gets more difficult for woman, who (if what I’ve heard is correct) can get hundreds of messages per day on some of the more popular dating sites. Making an active effort, though, can establish you as one of the good folks of the online social circle, and can only be beneficial to you down the line (you never know where being a good person will help you out in the future).

5. Use Correct Grammar/Sentence Structure/Spelling

This doesn’t matter as much to some people as others, but I can tell you that I personally have not continued conversations with people on dating sites for no other reason than because looking at their garbled and grammatically-incorrect messages hurt my eyes and my feelings. Typing is fairly easy for people of our generation, and it doesn’t take much extra effort to look for typos (most modern browsers will underline incorrectly-spelled words automatically, and offer to change it to the correct spelling if you right-click the word), make sure that your message makes sense and change the ‘4’s to ‘for’s, ‘2’s to ‘too’s, etc. This isn’t l33tspeak folks, and it’s definitely not texting in high school, either (unless you’re still in high school, in which case you should be making yourself stand apart by writing in proper English, anyway!).

6. Take It Slow

The biggest complaint that I’ve heard from women who have been members of online dating sites is that they’ll gets dozens of messages per day that will say things like ‘Damn gurl, you so fine. Why don’t you cum over and we’ll tap that ass?’ Let’s think about this for a moment. Who in their right mind honestly believes that this porno-inspired pick-up line will work? I can only imagine that the sender is treating online dating as a numbers game and that somewhere along the way he’ll come across someone just tasteless (or stupid) enough to fall for his ridiculous come on. Hopefully I don’t have to go any further with why this is the wrong approach because, damn, it’s REALLY the wrong approach.

The far better tactic is to take it slow, like you would meeting someone in real life (generally, at least..maybe the person above is used to doing the same thing in person? Yeesh…). Introduce yourself in a way that is clear enough that the other person isn’t freaked out or caught off guard, but intriguing enough that they want to write you back, find out more, and strike up a conversation. If you can’t come up with anything interesting to say, trying breaking through your writer’s block by writing your message in a non-standard format. When I’m stuck for the right words, for example, I’ll write in list-format (something I’m fond of doing in any writing situation, in fact). Point 1 would be ‘Hello!’, point 2 would be a one-line introduction of yourself, including your name. Point 3 would be why you wanted to contact them, point 4 might bring up a common interest. Point 5 would be your parting words, something about hoping to hear back from them, and point 6 would be your ‘Goodbye!’ or ‘Have a great weekend!’. Simple as that.

Extra points if you write your message as a poem. One that rhymes. THAT would be hard to ignore.

7. Ask Good Questions

This is a rule that applies to interacting in person as well, but it’s especially important in the online dating scene because it can be hard to get people to reply to you (whether due to the massive amounts of mail they get everyday or simply because they don’t know how to respond to your list introduction [see Tip 6]). Asking a few intelligent, well thought out questions, however, gives them a reason to respond, while at the same time showing something about yourself (‘if he knows enough to ask about that, he must be an MGMT fan, too!’). Asking good questions can help you steer the conversation while at the same time allowing you to be an active listener; that is, you are totally focused on what the other person is saying, and therefore finding out exactly what you want to know about them (which is one of the benefits of online dating…if you find out they are a Neo-Nazi or infrequent bather or something like that, you can ease your way out of the conversation by not asking any more questions).

8. Be Open-Minded

Good advice for life, but especially good for online dating. The truth is, you’ll likely end up going on a lot of dates before you find someone who you’d want to take things to the next level with (if that is, indeed, what you are looking to do eventually). I walked away from my dating experiences with a lot of new friends, and though I got lucky and found an awesome chick to date longer-term, I just as likely might not have, and I would have had to be happy with a double-handful of new friends. And I would have been, too, because I told myself ahead of time that whatever came of it I would at least have met some new people outside of my usual social group, gained some new (and sometimes quite bizarre) stories to tell, and tried something new (which should never be discounted).

This also means that you should keep yourself open to dating different types of people. I have a very definite type that I tend to gravitate toward, but I’ve found that when I’ve dated people who are very much outside of that type, I’ve been just as happy or happier even though they wouldn’t have fit my usual description of what I look for in a woman. The Internet opens up all kinds of doors, allowing you to connect with diverse groups of people from all over the world or just down the street. People who you would never meet in your everyday life. It’s worth the effort to try something new and unfamiliar, and a very easy and forgiving way to do this is to date outside of your comfort zone. Who knows? Maybe you’ll find that you were going after the wrong kind of person all along…

9. Know When To Pull the Trigger

It’s a fine art, knowing when to go from online conversation to actually meeting in person. I can tell you, too, that no matter how many times you do it, it’s still a little uncomfortable each time. Their voice never sounds quite like what you were expecting the first time you speak to them on the phone, they may seem a little bigger or a little smaller in real life than how they appear in their photographs. And you know this, at least subconsciously, so taking that step of asking someone out on a REAL date in REAL life can be an intimidating thing to do.

The best way to deal with this is to go with an old standard dating maneuver. If you’ve been talking to them for any amount of time, figure out something that you’d both enjoy doing and invite them out to do it. It can be as traditional as a movie or as crazy as laser tag (or glow in the dark miniature golf, as was the case with one of my dates), just so long as it has some significance to what you’ve been talking about (it could be completely random and unconnected, but generally something like that would be harder to work into a conversation).

10. Try, Try Again

As I mentioned before, you’ll likely have to go on many dates before you find the right person. The good part is, there are not many uncomfortable consequences for having a bad first date in the online dating scene; it’s not like high school or college where anyone you date knows everyone else you know and you have to see them everyday in Chemistry for the rest of the semester. No, you will be able to move on quickly, and so will they, and you should jump right back into the fray and try again. Persistence is a virtue with online dating, and being able to quickly acknowledge that something isn’t going to work will allow both of you to get back to your computers and strike up something new.

At the end of the day you’ll have met some interesting people, hopefully made some new friends, and when you finally do find someone you want to move on to the next level with, you will both have some hilarious stories to tell each other.

Share your online dating stories and advice below!


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  3. @Fernanda:

    Haha, well, it was over a span of time, so it wasn’t like I had a date every night for 18 days (though maybe that would be a good followup experiment? :)

    Truth be told, many of the dates were just awkward. I made enough friends (and ended up with one really rad girlfriend) that I will definitely be online dating in the future, and I imagine it will get even more interesting while traveling internationally (the language barrier, I’m sure, will lead to much hilarity).

  4. @Fernanda:

    Haha, well, it was over a span of time, so it wasn’t like I had a date every night for 18 days (though maybe that would be a good followup experiment? :)

    Truth be told, many of the dates were just awkward. I made enough friends (and ended up with one really rad girlfriend) that I will definitely be online dating in the future, and I imagine it will get even more interesting while traveling internationally (the language barrier, I’m sure, will lead to much hilarity).

  5. As a single mom looking to date again this may actually be some good advice.
    Would you recommend online dating though? Because so far I’ve only found creeps on the sites.
    Would you be able to provide of list of those 18 dating sites and which one did you favor, if any?
    Thanks and best of luck in your travels and adventures.

  6. As a single mom looking to date again this may actually be some good advice.
    Would you recommend online dating though? Because so far I’ve only found creeps on the sites.
    Would you be able to provide of list of those 18 dating sites and which one did you favor, if any?
    Thanks and best of luck in your travels and adventures.

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  8. Ah, clicked stuff in the wrong order. Feel free to delete other comment!

    Speaking as a girl who's tried online dating out, I've found it's pretty difficult to make any lasting connections. Ironically, the best friend I've made from one of those website is a girl (I'm straight)! My high standards probably also warded off potential meetings, but the few that I've gone on have been your typical awkward first dates!

    That said, I have had some pretty incredible philosophical discussions, the kind that's sometimes difficult to immediately jump into in real life. I'm on the introverted side, but I like to be very direct. Messaging can be pretty nifty for that. I'd say online dating can be a definite plus when you're easily intellectually stimulated, though of course you have to find similarly-minded (ha) profiles!

    And I am currently holding out hope for one of those philosophers :)

  9. I broke up with my long-time boyfriend about six weeks ago and, although I’m not quite ready to date yet, I know the day will eventually come. I’m already lurking on dating sites and talking to old friends.

  10. Bu Colin, what if the guy just can’t help being creepy? I mean, some people are JUST that. Unfortunately that means he has a laptop and mouse to spread his/her creepiness all over the original intent of online dating. Sigh.

  11. I have gone through the article really its nice its shows how important is to save our relationship. Keep posting great work.

  12. I met my boyfriend, now fiance, online. Too right, these ten things were the guidelines i lived by while on there. At the perfect time and place, he found me. Since our firat date some four years ago, we never dated anyone else after that. The chemistry was so strong we moved in a month after we made it official and has been living together for almost four years. There was so much that we enjoyed doing together that we never would have found out if we didnt take our chances. We just got engaged two weeks ago. So yes, it does work. Thanks, Colin.

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