Consider how creepy you are
When approaching a woman you have never met in real life, always ask yourself: "How creepy am I being right now?" More often than not the answer is very.
We want to believe you're a handsome, well-meaning guy, and not a 50-year-old toothless cretin with demanding kinks, but we've seen too many movies and heard too many horror stories to give you the benefit of the doubt. Until proven otherwise (as in, face to face), you are Patrick Bateman (though surely not as attractive).
Creepiness isn't just a "stranger-danger" issue—even men in her inner circle can create a aura of skeeviness. Before making your move, consider where you may fall on her creep spectrum.
- You haven't ever met in person
- You don't have any mutual friends
- You only know of her through her online identity (i.e., found her through her blog, Twitter account, or a random appearance in a Google search)
- You have mutual friends, but none of them are close friends who can attest to your character
- You've met in passing, but never had any real interaction before you made contact
- You went to high school or college with her, but haven't spoken in years. (Why are you emerging out of the woodwork all of a sudden? Alarms will sound.)
Being aware of where you might fall on this creepiness breakdown and taking any apprehensions you may be creating into consideration when you first approach her—these are the first steps to getting her to take you seriously.