For me it is when you are in a relationship. You can do it before then too, but sometimes as women we tend to jump the gun and move too quickly for many guys. If you move too quick a guy can feel the pressure of commitment that he isn't ready for. Some guys just need the space and time they get by taking the lead. I would say if a guy is really in to you, you cannot scare him away by suggesting a date, I am just not a fan of it myself.
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Anytime. The earlier the better.
The longer you wait ... I've lost interest a number of times. It feels like I'm the only one who is interested in a new date.
Who wants to date someone who doesn't seem interested? Never ever ever seem not interested.
There is no rule... if you like him then suggest a date anytime you want. It will show him you like him back.
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