• Jump into the conversation when it feels right.
• Begin with a simple "hi" and see where it goes from there.
• Give them a few chances to be shy, and then move along if no interest.
• Be creative. Try saying something a bit saucy, like: "boxers or briefs?"
• Once you have a prospects attention, send a whisper.
• Once you have a one-on-one chat going begin to share a bit more about yourself.
• Ask lots of lead in questions so prospect will open up with personal information.
• Put your cards on the table and tell prospect you are looking for a date.
• Establish all ground rules about how that date will take shape.

By this time you will be well on your way. Remember that when you are at a point where you will be comfortable with flirting online, by this time you need to be very certain of where this might take you.