Never had a real date

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I've had a few brief relationships but that sort of just happened, we never really dated or anything. I honestly have no clue how to ask a woman out. I've asked friends how they do it but they never really give the kind of answer I'm looking for. How do you know it is the right moment to ask someone out? How long do you have to know each other?

Sometimes a relationship happens on its own. My last relationship came out of college club meetings and a Skype session, where I just happened to be at the right place at the right time. Then three months rolled around and it was over. Life's funny that way. And I learned a lot in that relationship too. The asking out part just happened on its own.

the way i always worked it, was if i found out i had a common interest with someone, i suggested an activity around that that we could share.