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The complete guide to digital dating, guaranteed to maybe work

Online Dating Guide header
The Internet is by far one of my most favorite of man’s innovations for so many reasons – but one reason outweighs them all: It allowed me to find, meet, and end up with the most perfect partner I could ever hope for … all thanks to online dating.

Yes, friends, I am one half of a love match made by the Web. Given the many opinions and – ahem – constant evolution of the Internet dating scene, who better than a success story to help guide you through the process, its potential – and many – pitfalls?

Before we get started, a hopeful word for skeptics and beginners.

A quick disclaimer on why I think online dating works

JamI was a Filipina in Manila looking for a worthy pen-pal to exchange emails with. An experienced participant of long-term, long-distance relationships, I’ve never let proximity get in the way of true love and I’m a travel lover – so I signed up for OKCupid and didn’t limit myself.

jam's husbandI e-met an American living in New Jersey. He really didn’t know anyone in his area and worked from home, so he had very limited opportunities to meet anyone new.  He’d had a few girlfriends in the past and had tried casual dating for a while, but nothing had evolved into a serious relationship. And originally, he just wanted to find someone to hang out with and get to know.

For some reason, he landed on my profile, and I happened to be online.  Right away, I checked out his profile, liked what I read, and sent him a message. We struck up a chatting correspondence.

In a span of a month, we went through all the online “getting to know you” stages.  Epic emails of a thousand words each turned into daily text chats on Skype.  Then voicemail mp3s sent by email (because we were still too chicken to talk face-to-face, in real time).  Then finally, video calls.

Jam Skype
Image used with permission by copyright holder

Fact: If you meet someone you can talk to every day and every night and still find the energy to email five times a day and not get sick of each other, then that’s probably a great sign. And distance, plus the Internet, will force you to figure that out.

We both realized that early on.  He first told me how he felt by sending a Youtube link to “I Think I Love You” by David Cassidy.  I eagerly answered him with “If I Fell” by The Beatles.  A month and a half later, he arrived in the Philippines (after traveling 17,000 miles) to come be with his girlfriend for two weeks.  That was enough time to make him realize that I was the one, the one to make him go back to the States, sell all his possessions, quit his job, and come back to be with me.

After a full year of adventures visiting new places in the Philippines and Asia, I returned the favor and moved back to the U.S. with him.

Emotional pre-requisites

So now that we’re all starry-eyed and hope-filled, onto the serious stuff. For instance, you immediately need to ask yourself what kind of relationship are you willing to get into. Right now – ask yourself this right now if you’re considering online dating, because there are a lot of options. You can keep it platonic. You can play the field and openly date multiple people. You can get down to business and try to fine The One. You can connect with people in various parts of the planet or you can keep it close to home. Once you answer these questions, then the fun starts – and know that you are the only one in control of your online dating experience. When I got into online dating, I wasn’t really looking for a husband – I was just looking for a pen pal. I didn’t want to rush into the foray of real-life dating – I wanted to meet someone who was OK with the idea of building a solid foundation, and I chose my pen pals well.

Be open to the idea of pouring your heart out, because sometimes that’s what it takes to really get to know someone. Furthermore, the truth saves you a lot of time weeding through the bullshit later on (and weed you will), so don’t embellish or lie about yourself. If you want to write a thousand word email before you meet up with someone, just do it – a lot of online dating advice advises against this, but if it makes you feel more comfortable, then that advice be damned!

“Patience is a virtue” may be a cliché, but it is 100 percent applicable in online dating. Don’t be in a hurry to bag your first date – just like in real life, meaningful relationships are developed in due course. Also bear in mind that there are millions of people out in cyberspace also looking for matches online. Enjoy the search and take your time.

Have an open mind and suspend all judgments: Everyone is worth talking to at least once. If you find out someone is a liar or a creeper, you can always cease all communication and move on.

Things you need

Anonymous email: Before you even think about signing up for an online dating account, you must first ensure that you have an email address (duh) – one that doesn’t have your full name in it for safety reasons.

A webcam: It is imperative that you have a working webcam – I’d even go as far as telling you not to bother with online dating if you don’t have one. It’s the only real way of verifying someone’s identity prior to meeting up in person. One of the first guys I started talking to on OKCupid claimed he didn’t have a webcam. He also sent me a nude pic with the head cropped off (major red flag). Just for shits and giggles, I proposed an in-real-life meetup when I found myself in the U.S. on vacation near the town he said he lived in. He promptly disappeared from my online radar and I never heard from him again (he probably was this guy). So don’t buy the “I don’t have a webcam” crap. Besides, anyone can get it at Fry’s for a couple of dollars. If you’re dating for free on a website, have the decency to cough up a bit of dough for a webcam – it’s a good investment, trust me.

A Skype or Hangouts account: Have a Skype or any video chat account to supplement your dating profile. This is the reason why you needed that webcam. This works especially well for people who happened to find matches in faraway places. Back in the day, my husband and I used to have Skype dates where we’d watch the same movies or NBA games on our computers. He also met my entire family via video chat, too. But even for locals, it’s important for verification purposes.

Some social media self-restraint: Although adding someone you meet on a dating site on your Facebook might be OK, it’s not advisable early on (especially if you’re like me and use the site like a diary). If you need that connection, following them on Twitter is safer.

Where to online date

There are a bunch of online dating sites to choose from, and you are free to sign up on them all (if you can afford it). However, it pays to know what kind of demographic flocks to each platform if you want to narrow it down. GQ came out with a flowchart that you can follow, but please just use it as a rough guide.

gq dating site advice
Image used with permission by copyright holder

Personally, for anyone who’s new to online dating, I recommend OKCupid because of its user diversity and pretty accurate matching algorithm; I found it very easy to connect with a lot of like-minded people there. For those who are more comfortable dating “away from keyboard” and are only venturing into online dating territory to quickly meet someone new, I’ve heard a lot of good things about HowAboutWe. If you’re in a hurry to meet someone you could potentially marry, consider upgrading to a paid account on eHarmony (or any dating site, for that matter), but do your research extensively before pulling the trigger – you do get added perks for paying, maybe even better matches, but if it’s your first time online dating, try the free route first. If you have specific interests, we have a couple of suggestions that may (or may not) work for you.

Pre-gaming: Some tricks of the trade

Questions are hugely important – the more you have to ask, the higher your chances of meeting someone that piques your interest. Whether you’re an introvert who has a hard time socializing in real life or an outgoing person who can easily make conversation, asking questions is a great way to break the ice and keep the ball rolling. Of course, you need to also be willing to answer what you ask. After all, any type of relationship should be give and take, and online dating is no exception. When I first started online dating, I would send guys I was interested in short questionnaires (top five favorite movies/books/bands, what do you like to do on a Friday night, fondest childhood memory) and include my own answers to encourage a back-and-forth dialogue – and it worked really well!

It also helps to make a “My Ideal Mate” list. Sure, it sounds like you’re getting a little scientific with your romantic life, but it speeds up the process and can help you prioritize people.

And don’t skip the questionnaires your dating site of choice sends you; in fact, answer as many as you can! It may feel tedious at first, but try and think of it like a game. Not only will it improve how the site algorithm works to provide you a few potential dates, it will also help you know yourself and what you want out of a relationship.

And again, though it’s true that everybody lies, it doesn’t mean that you should. Reveal small portions of yourself bit by bit and know how to spot bullshit (please reference the webcam warning).

Girls, don’t be afraid to make the first move – it doesn’t make you less of a woman.

Lastly, bear this in mind: If you want respect, be the first one to give it.

What to put in your dating profile

User name

Keep your pen name classy if you want to snag a serious prospect – stay away from monikers that insinuate sex (bigtool4u, tits_mcgee, and thongman are out of the question). Be creative, simple, and memorable. And don’t intimidate anyone with your high-brow vocabulary. D0n’T F3eL t#3 neEd +o C0mPL!c@t3 UR username (it hurt my brain to even type that).

Profile photo

Profiles that have only one photo will be hard to prove authentic, so post at least three current (taken within six months, one year at the most) front-facing pictures (and only entertain suitors who do the same). One should at least show your face clearly, another should reveal a full or almost-full body shot (don’t crop out your head). Believe me, one of the things people lie most about is their looks and it’s way too easy to do – if you feel like you have to resort to creative photo editing to piece together your dating profile, then you’re probably not suited for it. If someone sees your picture and moves on, then a real-life relationship probably wouldn’t work anyway. And you, like anyone else, are allowed to be picky about this too.

dating online profile pictureMake sure your main profile photo is just you – no companions, no pets, no sunglasses, no props, no distractions. (Note: Don’t make a photo of you with the opposite sex your default pic. That should go without saying, but just know it sends the wrong message.) Feel free to showcase your personality through additional photos. Do not post any MySpace bathroom mirror photos.


Don’t lie. If you’re in the Philippines, say you’re in the Philippines. Even though you’re sort of sick of dating people in your area and would like to branch out, misrepresenting yourself through location is not a good idea – a lot of people are on online dating sites precisely because they are looking for dates in their area. You will be doing them a huge disservice by lying. If you want to attract people from other parts of the world, you can mention that in your description, which we’ll get to next.


You want to be as unique as possible in this area of your dating profile. This is your chance to tell the online dating world about who you are … so do it! Mention important hobbies. Veer away from adjectives like “simple” or “down to earth” or “laid-back,” get a little more specific than that. Instead of describing yourself in adjectives, you can reference a memory or things you do that best describes you; i.e.:

“I am the type of gal who listens to Queen loudly on headphones at work; I am also the type of gal who accidentally yells out the lyrics of “We Will Rock You” in the middle of a quiet office and doesn’t notice that the entire workforce is looking strangely at her.”

This type of description is creative and makes you stand out a little, and also offers clues about what type of person you are.

Oh, and another important thing to note: Run your bio through a spell checker, please. There’s nothing more embarrassing than a flurry of typos.

You also use ‘like’ and ‘dislike’ lists to describe yourself – just don’t go on and on. Mention random preferences about music, movies, TV shows, books, websites, food, vacations – anything that would interest you about another person. You are less likely to get skipped over by those perusing your profile if you go right ahead and mention actual artists, specific book titles, and the like. It is also easier to spot similarities and conversation starters through lists – back when I was still in the online dating game, anybody who mentioned Dave Matthews Band and The Princess Bride (book or movie or both) was worth talking to at least once.

If you are a Potterhead or a Whovian, by all means, mention that as well. These sorts of details will definitely provide you with a more pruned down match list.

An important thing to note, though: Although it is important to be as descriptive as you can about yourself, don’t feel obligated to reveal every single quirk you have – leave some mystery.

If you have to mention pet peeves, do it sparingly. You don’t want to seem too nitpicky or unintentionally exclude too many people – it’s better to keep your profile on the positive. Also, refrain from talking in the third person or resorting to sarcasm – it rarely translates well online.

End your write-up with an invitation to continue the get-to-know process through a private message or chat. That’s it! It wasn’t so terrible, was it?

Oh, and another important thing to note: Run your bio through a spell checker, please. There’s nothing more embarrassing than a flurry of typos. 

Avoiding stranger danger

Everything is essentially public on the Internet, so don’t be liberal with personal information too early on. Introduce yourself to a prospective match using a nickname and wait for things to progress before sharing more pertinent details.

Talking on Skype is better than talking on a landline (what the hell are you doing giving away your home phone anyway? Don’t do it!). It gives you a sense of availability and distance at the same time. It’s also not as easy to track someone down using a Skype account; a home number, on the other hand, is easily traceable and can lead to all sorts of sensitive information you don’t want to dish out.

And here is an unfortunate reality: A lot of matches out there are actually married, and most of them will never mention it. Believe me, you don’t want that kind of drama in your life. Learn to identify and avoid married people.

Be open, but be cautious as well. Find the balance between.

Making the first message move

When I first messaged my now-husband, I referenced something he said in his own profile, a tried-and-tested method for making the first move and beginning a genuine conversation. And while I thought he was handsome, I decided to say I thought he seemed interesting – as a general rule, I stayed away from commenting on a person’s looks right away. Commenting on a photo’s environment or an artifact in the shot or an article of clothing is acceptable and may even be an effective conversation starter, but exclamations about how damn hot someone is aren’t advised – it’s rude, and often-ignored … and way too soon, guys. Too soon.

Instant chat rarely brings out the best in people (all I ever got was “yo” or “sup” and a lot of “hey sexy”)

Be funny, but the right kind of funny: Avoid dirty jokes (they never work, anyway). Bring up specific interests that’s important to you so the person can quickly get a sense of what you’re like without having to check out your profile.

End your message in an open-ended manner – with a question, or invitation to chat. Instant chat rarely brings out the best in people (all I ever got was “yo” or “sup” and a lot of “hey sexy”), so don’t even enable the function. A lot more progress can be achieved through private messaging.

Again, let me re-iterate the importance of spell checking. Netspeak, bad spelling, and bad grammar can be deal breakers.

The first response

The great thing about the first response I got from my husband was that he dared to me think by asking a question, and he made me feel more at ease by answering it himself. When responding to a message that has a question, answer it as best as you can and respond with a counter-question (which you also should provide an answer to) to encourage a repartee.

Not interested? If you’re not feeling the sender of the message, don’t feel guilty – all is fair in love and online dating. Deleting or ignoring meh messages is OK, but you can also opt to be nice and let them down nicely if you’re not interested. Here’s a rejection letter I sent someone who was about 20 years my senior:

Dear Sir,

Thank you so much for your interest in getting to know me on a deeper level. Thank you for the award you gave me as well. That was so kind of you.

Friendship’s okay; I’m not one to refuse that to anyone who asks for it. But I feel like I must tell you frankly that as of the moment, I am prioritizing conversations with guys my age, so I might not be able to maintain a correspondence with you. After all, this IS a dating site.

I do hope things work out well for you and that you find the woman of your dreams.

Keep on writing!


I sent this nice response since he, too, had been polite. Of course, if you come across a d-bag, then all bets are off. Respond as you see fit – just don’t let it escalate.

Maintaining an online relationship

First, a disclaimer: If you want to get into an online dating site, find a match, score a date, and get out, by all means go for it. Online dating is, for all intents and purposes, a means to make meeting people easy – it’s why you’re encouraged to meet up with people on the site in real life. In my personal experience though, I’ve had better success after really developing the conversation online first. This gives long distance matches a real shot, too (people tend to rule them out because it is too much work, but allowing it to be an option significantly widens your shot at relationship happiness).

I can’t say for sure what it would be like to message someone and immediately set up a real life date, I made a rule for myself – sort of like the “no sex before the sixth date” rule. My interpretation: no visual communication (virtual or in person) before the sixth email, and it has never failed me. Those who fail to make it to six don’t get the chance to see me, even from a screen, and those who do are gifted with more of my stories, complete with appropriate facial expressions and hand gestures!

But say you find yourself dating someone you met on a site – and you don’t live near each other. Then what?

If you do find someone not in your time zone, make sure to keep a consistent conversation flow. In my case, even though Manila is 12 hours ahead of New Jersey, I made sure I sent out an email a day, and he gladly did the same. He had a full-time job then and was often unavailable when I was, so we’d schedule text and video chats in levels: L1 for purely email, L2 for text chat (through Gmail) with intermittent responses, and L3 for full-on Skype video chat. It was effective because it allowed both of us to carry on with our lives and at the same time, invest enough time on our budding attraction. Of course, this was once our relationship became more serious, so don’t go whole hog on the Skype schedules right away. Letting things happen organically is important.

Like I said earlier, if you find someone you can talk to for hours, write and chat with simultaneously, video chat and still have a lot to talk about, then you’ve got yourself a catch. If you happen to come across a person who loves to write and communicate through letters, I heartily advise that you give it a shot.

Taking it offline

If you choose to really develop the relationship online, then the first real life meeting probably won’t be so scary. The great thing about all the time my husband and I spent getting to know each other online is it completely eliminated all the awkwardness and fear during our first meeting in the flesh. It honestly didn’t feel like the first time – at that point I already knew so much about him that it felt like we’ve known each other for years, a great sign of great things to come in any new relationship.

online offline dating
Image used with permission by copyright holder

But if you’re a casual dater on a first date with a recent online match, know that it’s just like any other arranged date – talk about what matters and ask a lot of questions (and really listen). If it’s your first date ever, just remember your date’s profile and draw conversation inspiration from there. And don’t feel silly for thinking of conversation starters in advance when looking over your date’s profile. Not to make it sound horribly unromantic, but you’d do the same for a job interview, right?

Make sure you set your date in a neutral location that’s not too close to your home or place of work. This will make it easier to stop seeing an online dating find should your date go horribly wrong. I’m not saying it will, but it might – it’s better to be prepared.

If you do end up with a bad first date experience, don’t feel like a jerk if you have to be the one to let someone down (it has to be done). It’s rude to explain why the date went poorly based on the other person’s attributes, so word things so that they come back to you – you just share their interests; you wish you had, but you just didn’t feel a spark; you had trouble keeping conversation going.  Of course if your date was somehow horrible, then you’re allowed to tell them why you won’t be meeting up again.

Online dating can lead to awesome – so dive in!

Yes – I met my husband thanks to online dating, but it also helped me dig deeper and take a hard look at myself and what I wanted out of life, not just in a partner. Enjoy this self-reflection. If you don’t end up finding someone you like online, the experience can still better equip you mentally and emotionally in finding someone.

Don’t treat online dating like a never-ending buffet (even though at times it will feel like one). From your many matches (who actually respond and show interest), only choose a few to develop connections with. Your best case scenario is you end up with a fruitful relationship; your next best option is good ol’ friendship. At the very least, you will come away with a hilarious story about that one time you tried online dating.

To end on a hopeful note, here’s my last piece of advice: Don’t get discouraged if the first few online acquaintances you make don’t pan out; try and try again! Online dating can actually become fun if you spend some time investing yourself in it, and when you hit the jackpot, you’ll be glad you stuck it out.

Take it from me. I am glad every single day. Sorry if that sounded like a humblebrag …

Jam Kotenko
Former Digital Trends Contributor
When she's not busy watching movies and TV shows or traveling to new places, Jam is probably on Facebook. Or Twitter. Or…
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