You might find an extra challenge in coming up with a reason to start talking to him, but, who knows, you might actually have a meaningful conversation rather than just random flirting. So, you might consider taking a few minutes to brainstorm some ideas before you walk over to him. So, if you want your first interaction with him to turn into a second one, try just being friendly the first time you talk to him.
Let the flirting come naturally in the course of your hopefully future interactions. Because I can be prone to talk with no end in sight, I find I have to consciously stop myself and actually give the poor guy an opportunity to talk back. After all, they call it a conversation for a reason, and the idea is for both of you to talk!
You never want your interactions to be a one-way conversation. I had two best friends in high school who were shy, and I had the realization fairly late into our friendship how one-sided our conversations were. Most of the times we hung out consisted of me talking and them listening, nodding or agreeing. I love asking questions! Still not looking at you? Your heart is beating quickly and your pits are moist.
The thing about shy flirters is that they want to make and not make eye contact at the same time. Typically you should be able to recognize the difference. Being that sarcasm is so casual these days, being cynical has become a really simple, comfortable means of modern flirtation.
For example, anyone liking your status updates back in is suspect. Opportunity To Flirt Nothing. Smiles are a safe bet because everybody smiles at everybody.
Another commenter agrees with the nature argument, saying that not trying to flirt is when flirting happens most naturally.
People naturally gravitate towards others who are confident in who they are. If you can do that, flirting will come naturally. One modestly experienced commenter in the realm of flirtation says women respond better to him when he treats them like a person rather than a conquest.
They are just a person who may even be a little timid around you, too. So yeah, just try to be comfortable and be yourself. There are nice guys , and then there are Nice Guys.
Be a nice guy, not a Nice Guy. Keeping the creep factor low and prioritizing respect may sound like a given to any actually nice guy. But we live in a world where the obvious needs to be stated and kept in mind, especially when approaching women you might now know well.
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