When you’re planning a first date the biggest question is whether or not to commit to a meal versus just meeting for drinks. Well, I have the perfect solution! Make plans to meet at a restaurant that has a bar… and make reservations for dinner at that restaurant about an hour after you are to meet. If there is chemistry and conversation during the drink portion and you’re interested in getting to know your date more, then go ahead and follow the hostess to your table. If you don’t want to continue the date, then thank your date for his or her time and leave.
That said: you must check-in with the hostess ahead of time and let the restaurant know that the reservation is contingent upon the date going well and that you may end up canceling. Arrange a gesture or look that you will give the hostess if you want them to come and get you when it’s time, or not. (Or you can also walk-in without a reservation and if you are enjoying your time at the bar then go over to the hostess stand to ask for a table. If the wait is too long and you still want to stay, then order food to the bar.)
It may sound like a big hassle, but it solves a lot of issues about how to plan a date when you aren’t sure if you’re going to like the other person. You want options and you want to eliminate awkwardness. If you’re unsure when the time comes to go to your table, then take the plunge and sit down for dinner — sometimes people have nerves and the transition to the next stage of the date should help.