You can ask them a generic question and get a casual conversation going. Once you’ve exchanged pleasantries and greetings, you can ask the mandatory “getting to know you” questions.
Remember, the hardest thing about flirting with someone online is getting over that fear. These include things like what they do for a living, favorite past times, and things of that nature.
Always keep in mind that there will always be a very fine line between being flirtatious and being a jerk.
To avoid crossing that line, stay away from personal subjects that could offend the other person and hurt their feelings. Emoticons are the perfect way to show the other person that you’re only teasing and actually flirting.
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