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One common reason to delay a first date is due to an attempt to learn more about the other person. I found the first few minutes of the first date are worth more than dozens of emails.
Another reason to delay would be if the person you are communicating with has expressed extreme reservations about meeting people from the internet.
Your date might remind you of your time constraint (“But I thought you needed to be home at 8…”). People who are dating online actively will appreciate your planning for a bad date and like the fact that you are saying to them “this is a good date”.
If you would rather not let them in on your planning for the worst-date-scenario, just say that you’d prefer to cancel your previous plans and spend your evening with them.
If this happens to you, wait a few days (continuing the email conversations) and then ask again.
Unless a good reason is give for not meeting, I would not ask more than three times – there are some people out there who are looking to make online friends or live fantasies out in their head without any intention of actually meeting.
If you enjoy talking on the phone or prefer to do so before meeting someone, treat this step like you would the first date by asking for the phone number by the third email.On my first date with my wife, I schedule a one hour date at a diner.After the hour was over, I explained that I only extend the good dates and since ours was a great date asked if she would be up for miniature golf (she was).By this point you have talked back and forth twice and can measure how well you are getting along.You will be able to judge the situation better as you communicate: sometimes you’ll get a date on your first email, other times you may realize a few weeks of communication would be best.