Do's and don't's of asking someone out

Although I would identify getting someone's number as the apex of the meeting/flirting/dating process, I've noticed that an appallingly significant number of people struggle with what I would consider the home stretch: asking the person out. There is no singular right way to do it, but there certainly are (very) wrong ways to do it.

There are two factors to consider in the way that you ask someone out: medium and content.

Medium

• Asking in person or over the telephone is preferable--almost to the point of exclusive acceptability.
• Texting is NOT okay. Do NOT text to ask someone out. If you have his/her number, call. Calling will demonstrate your confidence and that you respect the person enough to make the effort.
• Use Facebook only if you have no other way to contact the person. Send a message; do NOT do anything public like write on his/her wall or post a status. Ideally, you would send a message asking for his/her number so that you could then call to properly ask him/her out, but if you feel that that would unduly complicate the situation, just keep it to the one step.
• Do NOT tweet. This may sound absurd to some (hopefully most or all) of you, and I certainly never thought that I'd have to explicitly discourage this behavior--until it happened to me. Again, only if you have no other way of contacting the person, send him/her a direct message (or, if (s)he doesn't follow you, tweet at him/her asking for a follow so that you can send a DM--but keep in mind that if you are connected to this person only through Twitter and (s)he doesn't even follow you, you might want to think twice about how appropriate it would be for you to ask him/her out).
• Bottom line: choose a medium that allows your request to be private, sincere, and respectful.

Content 

• Propose a specific plan, including both activity and time frame. If you feel that this is not sufficiently accommodating, you can propose two alternative activities and time frames, or, if, for example, you suggest dinner and a particular show, you can let your date choose where to go for dinner, since you chose the show. Of course, let your date know that if this plan is not pleasing to him/her, (s)he can feel free to suggest something else. Here are some examples: "I'd really like to [take you out to dinner and a show at Jazz Alley] [take you to see the Medieval Ivory Chessmen exhibit at the Met and then to dinner] [take you to lunch and then go to a pumpkin patch] [take you to brunch and then to the zoo]. Would [Tuesday] [Saturday] [or you can suggest multiple days] work?"
• Do NOT say something vague and half-assed like, "So when are we getting together?" or "So when are we gonna go out?" You might prefer this tactic because you think that it seems casual and fun or something, but it is not a proper method--there are other ways to convey these attributes, which you should have done already.
• Going the specific plan route as opposed to the open-ended, "Would you like to go out with me on Wednesday?" route demonstrates your creativity, personality, and, as always, confidence. As described above, you can be accommodating without being boring or weak. Use as much information as you have about your date when choosing which activity to propose--for example, if you know that (s)he likes sports, suggest getting dinner and drinks while watching the game in a bar/restaurant, and if you know that (s)he hates sports, don't suggest this!

Good luck! As always, contact me if you have any questions!