Go on a night walk through the city. See the same places at night, when there are no people on the streets, lit only by the moon and the lights of the city. Remember to select save areas and obtain a pepper spray just in case.
At night, when you are alone you will not pretend anyone who "you should be". You can prepare the topics for discussions on such topics which you always wanted to talk and there was no time. This time you will have it a lot! :)
That the whole expedition was a success, be rested. The best that it was a day off from work, if you sleepy date may lose its charm. Before the walk, plan together what you want to see and avoid a situation where you're stuck in a boring place without a plan for the rest of the evening.
Also look for interesting restaurants or pubs near your route. It is important to check whether venues are open all night. If you find any interesting place, you can go there and order something what you want, for example a glass of wine.
In preparation for this night dating, first, take care of security. Select a safe area, Load up your phones, and preferably tell someone close, such as a friend or sister that you are going for this type of adventure. You can also obtain the audible alarm or pepper spray. Never be too careful.
After an overnight date, eat breakfast together. Omelet or scrambled eggs, orange juice or anything else. When you finish, it's time to sleep after the restless night. Good luck! :)