Ok. So let’s get some safety stuff out of the way before we learn how to properly stalk someone on the internet. Internet stalking is not for the uninitiated and should only be attempted by an amateur. Professional stalkers are spooky and creepy and you should watch out for them. They can also be dangerous (especially if they’re total strangers). If you think you’re the victim of internet stalking by a complete stranger, here are some links to check out: Cyberstalking FAQ, Info, and Cyber-911 Tiplines.
Now, all that aside, there’s also plenty on the web regarding how to stalk someone the right way. Surprisingly (or not), most of the posts I found are by women. Bonnie Burton’s suggestions are here at “Relationships 101: How to Stalk Without Being Creepy“; also check out former Boston College student Christina Bechold’s 2004 piece “How To: Stalk Your Crush“, and Sarah Austin’s (nee Meyers) short 2007 piece “How To: Stalk on the Internet“. I haven’t tried CoComment myself, but (frankly) it makes me a bit nervous.
Teenager Marco also has some words of wisdom in his (also 2004) piece “How To Stalk Me” – “All I ask is that you do it properly. I have prepared some simple instructions and guidelines to ensure the best quality stalking experience for both of us.”
Wikipedia has an article here, though it’s not as comprehensive as one might expect.
The above links should get you started. For myself, I prefer to avoid any possibility of detection – even though a particular route is more likely to garner more (useful) information. For example, don’t “follow” someone on Twitter, just flip to their page every once in a while – it’s not as efficient, but just as effective while preserving one’s anonymity.
Problems occur here and there when two people stalk one another. This can make for awkward and uncomfortable situations replete with BS excuses. In such situations, I find honesty to be the best policy – people rarely admit to “stalking”, so the other party usually thinks I’m joking.