6 Ways to Ask Someone on a Date

1. Don't Specify a Time When You Ask

"Would you like to go out Tuesday night?" is easier to reject because the other person may have plans that night. More importantly, it stresses a sense of formality--a specific time and place, to be scheduled in like a business meeting--that may make the other person uncomfortable. "Would you like to get together sometime?" is much better because it emphasizes casualness and flexibility. The other person is free to find a time that works well, giving him the ability to choose rather than simply being told a time. In addition, the informal tone of "sometime" stresses a more relaxed attitude that makes it easier for both parties to feel comfortable.

2. Don't Ask When the Other Person Is With a Group of Friends

Social situations tend to put the other person on the spot, raising her discomfort level and making it harder to feel at ease with the situation. Find a time when the two of you are one-on-one and work the question naturally into the conversation. The social concerns will be removed and the other person is much more likely to respond positively.

3. Plan Something Casual

Excessive formality is a no-no when asking someone out on a date. It creates unreasonable expectations and puts a lot of pressure on the situation when friendliness and relaxation should be emphasized. A casual lunch, dinner at an informal dining spot or a trip to the movies are much more appropriate than anything more formal.

4. Make Specific Plans, But Provide for Some Flexibility

While you want to emphasize the casual nature of the date, you also don't want to seem like you have no idea what you'd like to do. Your choice of activity should be fairly specific, such as dinner, a movie or an amusement park, though it can certainly emphasize a flexibility. For instance, you can ask your date out to dinner, but plan to meet at a place which offers several restaurants to choose from. Or you can go to the movies, but leave open which movie you'd like to see.

5. Allow Your Date to Meet You at the Location

In previous generations, it was considered mandatory for the boy to pick the girl up and drive her to wherever they were going for the date. These days, it's more appropriate to meet at the location, at least for the first date or two. Again, that enables a casual atmosphere and allows the date to feel like she has an "out" if required, which helps your date stay relaxed and focus her interest on you. It is also a safety consideration if you are going out with someone you don't know well.