There comes a time in everyone's life when they will develop a romantic interest in someone else. However, for many people, taking this attraction to the next level and getting up the courage to ask the person out is quite a different story. The fear of refusal is quite common, so it comes as no surprise that people are often seeking the perfect way to ask someone out. This Entry will discuss a variety of possibilities and logistics concerned with the art.

Sexual Politics

Who should do the asking? It's a question that perhaps matters less today, when women are seen as independent and capable of asserting themselves. However, many people, possibly considering themselves 'old-fashioned', 'traditional' or 'romantic', believe that the man should ask the woman. It all, of course, depends on your point of view, but there is no reason why a woman should feel that it's inappropriate to ask out a man, instead of the other way round. In fact, there are some situations, such as a 'Sadie Hawkins' dance (popular at many American high schools) where the entire premise is that the girl should ask the guy. There is no hard-and-fast rule on this, though. If you're female, don't let yourself pass up an opportunity simply because you think he should be asking you.

If the object of your affections is of the same sex, you're at least free of the who-asks-whom question, but it's unfortunately necessary to be a bit careful. Before you ask the person out, you may want to ensure that your respective communities, families and friends will not reject you for being an 'out' same-sex couple — otherwise, it might be wise to keep it quiet or wait for a time when you're free of such constraints.

Possible Media

Though it does take courage, it's generally thought that asking your special someone in person is the best bet. It will mean more if you can explain your thoughts directly to the person, giving them a chance to reply to you, instead of writing them a letter or sending them an email. In the technological age, it might not be considered inappropriate to ask the person on the phone or through instant-messaging — though if you're feeling too shy or nervous to ask the person out to their face, perhaps you should consider whether you feel comfortable enough with them to go on a date or even go further than that.

Getting Creative

Many people like to find interesting ways of asking out the objects of their affections, and just as many people dream of being asked out in an imaginative manner. This phenomenon seems particularly common among teenagers, who may decorate each other's cars, send each other flowers or hang signs outside each other's schools and houses. They also might try to find original ways of popping the question face-to-face, under the assumption that a particularly unusual or romantic format might convince the other person to say yes.

While originality should of course be encouraged, many of these techniques are not as original as one might like to think. People have been asking each other out for thousands of years, and chances are that if you can come up with it it's been done before. Also, you should consider your audience — your subject might be the type who would appreciate a bouquet and a mushy card, but they might also prefer you to get straight to the point and ask them on a date without calligraphing the issue.

Making Contingency Plans

While it's not a good idea to get too cocky and assume the other person will say yes, if you always expect refusal you're not presenting a very convincing argument. Pose your request earnestly, but be prepared for either a 'yes' or a 'no', and think about what you'll say to either response. If they do say no, it's probably best not to press the issue. Pleading for them to change their mind, saying something like 'Let's just try it this once and see how it goes', or assuring them how much you love them may pressure the person into doing something they aren't entirely comfortable with — which will not make for a very comfortable experience.

The Other Side of the Coin

Put yourself in the other person's shoes and think about how they might receive your request. It could be something they're expecting or it could come as a complete surprise to them — you should think about what effect you want to achieve and what might make them most comfortable. For example, if you think they'd prefer not to be surprised, you might try getting to know them and dropping subtle (or not-so-subtle) hints beforehand.

Also consider your motives, and how they might be received. If your interest in the person is purely because you find them attractive, this could easily upset someone who would prefer to be taken seriously as an individual with a personality. Always remember to treat them the way you'd like to be treated — respect is very important.

If you're shy about asking someone out or simply see them as someone to be 'just friends' with, there are of course other solutions. Going to see a movie does not have to be a romantic occasion, for example, and if you're going to a party or dance you could agree to go as a Platonic couple. If you're just feeling nervous, though, remember that you'll never know until you ask — they could very well say yes.