When to confess your feelings?

It really depends on how long you've been together and how well you know each other imo. Like some others have said, after you both get a feeling for what the other is like and what makes them tick, give them little hints and see if they catch on. Chances are if you two know each other well enough they'll start picking up on your intentions and get the message you wanna date. You don't have to be super formal or super subtle with it either. Casual confessions work well too. I think one of the biggest things to remember isn't just timing but being content enough with yourself to be able to ask the other person. Know who you are and what you want, and be realistic about it. Evaluate other possibilities and don't throw all your eggs in one basket. You'll take a LOT of the edge off asking someone out that way, and if they reject you or want to wait a bit it won't hurt as much. I know I was super embarrassed when I first asked my current bf if he was interested at all in me, and my head was spinning with the worst possible reactions he could have to it. Luckily it turned out he was super into it and we really hit it off, but in retrospect I don't know if I could deal with the anxiety that comes with putting myself on the edge like that again.

Well it depends on what you mean by confess. If you mean, Hey I want to date you. Immediately. Absolutely as soon as possible. The longer you wait, the longer you leave that chemistry to fade, and turn into a comfort zone of platonic friendship for the other person. However, if you mean like, "I Love you, Have my babies, Let's buy a house together, I want you forever!" Wait until after at least a few dates. (Be them online or physical, preferably physical, as it's easier to build rapport with it.) If you do it immediately, You'll only come off as needy and desperate.(Same goes if you start saying I love you constantly, sure it's great at first, but then it starts to lose the special spark it has.) You want to know how the other person feels first, usually, and that doesn't mean they confess first, but knowing the signs of high attraction. However I imagine you're going to do it off the internet, so it's far harder to learn that without body language to go off of. But when a girl wants to spend time with twenty four seven, while you're dating, she's usually grown a crush on you. That doesn't change with the physical or internet. So my answer for the more likely #2 question. Wait until you know she's having feelings, and if you don't know how to tell, look it up and learn, because trust me, it's a useful skill, for starting relationships and keeping them. But let's just say you don't have the time to learn, then I would say (AFTER Dating around three or four times.) Three weeks. maybe a little bit less, or a little bit more, depends on how hard you're both hitting it off. Then confess, and ask her to be your girlfriend.