Approach her with a genuine smile. As simple as it seems, a genuine smile will get you off to the best start. Smile exactly as you do when you are happy. Don't fake it--a fake smile will show. Smile with your eyes and not just your mouth. However, don't smile the whole time or you will just seem creepy.
Ask her out in a way that gives her the option to either turn you down gracefully or accept without feeling pressured. You don't want to go out on a date with a woman who is just there because she felt pressured into it. Nothing good can come of that, usually. You can say, for example, "If you don't have plans on Friday, would you like to go out to dinner?" This gives her a way to turn you down if she does not want to go out with you. If she answers that she has plans, and does not follow that answer with a suggestion that you and she go out another time, it is safe to assume she is not interested in going out with you at the moment.
Speak assertively but not demandingly. There is a distinct line separating assertiveness from authoritativeness. Men sometimes mistake being a bully for being manly. Nothing could be further from the truth. Desiring power over others, and bullying them to get it, is usually a sign that the person doing the bullying has little real internal power. In contrast to this, people who are assertive are people who have a healthy self-esteem. They know their own inner strength and accept who they are and do not need to get a false sense of power by forcing others to comply.
Prepare yourself mentally for a "no." Be a good sport about it. If a woman says she does not want to go out with you, accept it and move on. If she changes her mind later, it is very likely she will let you know. If you pressure her, however, she is more likely to become annoyed, or worse, and you will look like a desperate, overbearing creep.
- If your love interest says she would love to go out with you, feel free to let your joy show but avoid looking like a gleeful puppy
- Don't beg. Begging is not ingratiating and it is not cute.
- If you are turned down, let it go. Move forward. Do not insist and do not ask multiple times. Asking a person over and over if they will go out with you is harassment.