How long before I should ask someone out?

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I didn't hear back from the miss oil rig worker for a few weeks so I thought I'd look at some other profiles on OKCupid. I sent out some messages. I started conversations with two of the girls I messages in addition to one girl who messaged me.

I've been chatting to the three of them for a few hours but my question is, how long should I chat before I ask one of them out? I know some girls get scared if you ask them out too soon and some girls get frustrated if you take too long. In some ways the medium of text is quite limiting because I can't see or hear them. How do I know when a girl is ready to be asked out online?

There is only one way of finding out when to ask for a date - you ask for a date!

I'm not knowledgeable, but I suspect that if a girl is on a dating site, she is already interested in dates.

Hey, you were right. It worked. Now I've got a date for tomorrow

I usually wait for 4-5 message exchanges, depending on how well the conversation is going and how comfortable she appears to be with meeting in person based on her profile. Protip: I'd recommend staying away from the "Chat" on the site and sticking to the messages, and trying not to send more than like 1, maybe 2, messages a day to any given person so that you don't smother them with contact.