Ask questions when you are planning your date.
One of the most disastrous mishaps that can easily be avoided on a first date is planning to go someplace where the woman you are trying to win over will dislike or feel uncomfortable. For example, taking a vegetarian to a steak house or a salsa dancing club with someone who recently suffered an athletic injury. It's easy to find out about food allergies or even make a joke out of asking a woman what would be the worst possible date ever. Your humor and consideration will be appreciated.
Start to create a flexible itinerary for the date regardless of the time of day based on the information you obtained while asking her out.
Use a local dining and entertainment guide to plan your date. If your date is happening early on, check out bistros, coffee shops, mid-day concerts or museum times and shows. If you have an evening engagement, check out restaurants or movie, theater or concert times. If you are prepared to explore one neighborhood in particular, you can spend more time on your date and less time traveling to get somewhere. Jot down the options in a mini notebook to stay organized.
Pay close attention to any signals your date may be directly or indirectly communicating while you're on the date.
If she is having a great time walking around museum exhibits, perhaps you might spend more time there then you anticipated. Or, if she decides that waiting an extra half hour for the movie that has really been on her to-do list is also okay. You don't want to come off as rigid or as a man that lacks spontaneity. Being prepared and proposing a plan is impressive, but demonstrating the ability to handle the unexpected wins even more points.
Do things, such as compliment her on something small, open her car door, help her into the cab first, pull out her chair, maintain an appropriate physical distance based on her comfort level and take the initiative when settling up the bills.
Unclear gender roles can make gentlemanly behavior seem like a novelty in the modern dating landscape and your date will most certainly take notice of thoughtful gestures. She'll also help to set the tone or express her personal opinion on any action you take, but set yourself up to exceed her expectations.
Give your date full eye contact frequently throughout the night and be sure to bring up an inside joke or continue conversations that have emerged throughout the date. This is where self-confidence plays a huge role. Smile often and present a picture of a happy and successful person proud to be who you are. No matter where you go or what you do on the first date, having an enjoyable time with the person should be the first and foremost plan of action.