The complete guide to digital dating, guaranteed to maybe work

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

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 … 

Page 2 of 2


Get our Top Stories delivered to your inbox: