I always saw the second date as the “physical activity date”. We would go bicycling, roller blading, minature golfing (along with swinging the bat in the batting cage, of course), Frisbee golf, ice skating or anything similar and available in season.
I always felt that it should be able to be done not that far from home, however. None of this drive 150 miles to hike in the mountains on the second date. Instead go to a nearby place where the above mentioned things are available (word to the wise, don’t choose something that you are fantastic at unless your date is also. If you do it will be boring for you and frustrating for your date basically negating any third date).
Of course, this should be capped off by dinner or late lunch at a charming or downright weird bistro while still in your athletic attire. This place should not be a chain place however, no matter how strange it is, it should be unique and be a place where you can talk.
The third date is the “culture date.” Save the museums and galleries for this date. Take in at least two. Follow the cultural activities with either bowling or other indoor activity like pool. Cap off the evening/day with a sleazy bar that serves great ethnic food.
The fourth date is the “prove that you can cook date”. My speciality used to be spaghitti with meatballs (easy to make but with romantic overtones-remember Lady and the Tramp) with chocolate chip cookies for desert (shows you’re still a kid at heart). Lots of good wine was a necessity. You end the evening by sitting on the front porch/stoop, balcony still sipping wine and watching the people go by and greeting them in nice ways.
This probably sounds a bit methodical, but it worked for me. These were planned out but always allowed for a certain amount of spontaneity also.
A hint: Don’t let reservations dictate your date. Make reservations under a number of different names about every 30 minutes or so within the window you expect to be at your place of dining. As the date progresses, cancel the ones you know you will not make, if possible.
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