When you like someone and you want to chat with him or her, start it off with a joke, an interesting comment or a pick-up line. Don’t ask personal questions you could easily find the answers to, especially if that person shares a lot of things online. Instead, find common ground and talk about it. Go with your strengths, or read up on his or hers. That way, you can ask informed questions and not just blunder about. People like to talk about their interests, but not something easily googlable.
Remember, being cute is just one step towards getting to know your crush more. It helps to be witty as hell as well. Good luck! Hope you get a Valentines’ date!