I would say there are three things that are important for making connections online:
1. Targeting the right people
2. Adding some sort of value to their internet experience.
3. Asking open ended questions
Targeting the right people
The first point may sound a bit weird.
"Targeting" a person for friendship online might seem a bit cold, but the internet is a noisy place, and to me this actually makes a lot of sense.
Imagine you were in a really busy bar or park, and some stranger came up to you and said "hello, how are you doing?"
Although they might seem friendly enough, you might have a voice in your head asking "why have they approached me out of all these people?"
However, if they immediately have something in common with you (a shared interest, members of the same group/society, fans of the same sports team) and bring that commonality up in conversation, then this makes you feel more at ease.
The same thing applies to sparking conversations on the internet.
So someone that opens with "Hey, I read your comment on that article about The Doors, and they're my favorite band too!" stands a stronger chance of getting a conversation going than someone who messages you saying "Hey, wanna chat?"
Adding value to their internet experience.
My second point is based around a similar concept.
Let's say you write a blog post about a vacation to Italy, and you receive two comments:
- Nice post.
- I had the same problem during my first trip to Florence. I found that the restaurants with the least tourists in them tended to be a lot cheaper, and served nicer food too!
Which comment would you feel most likely to interact with?
Probably the one that has taken the time to add more value to the conversation I'm guessing...
Ask open ended questions
This is actually a sales technique, but can be applied to pretty much any conversation.
If you ask questions that have a yes/no answer, you run the risk of ending the conversation abruptly and having to start again.
"Do you write about Italy often?"
Now the conversation needs to start from scratch.
Instead, with an open ended questions there is more room for conversational flow:
This might not work everytime, but it's a tip I've found useful.
"What made you want to write about Florence over the other cities you visited?"