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How to Ask Someone for a Date

You have several options when asking for the date. The choices may be influenced by circumstances (like distance), personality, and personal style. In general, the closer you are when you ask, the better. When you’re close to the person, you get more information, you appear more courageous, and you get some practice for the date.

You can adapt any of the following methods for sending the message to your level of comfort. But be careful that you’re not hiding behind your comfort level — sooner or later, you’re going to have to get out there and actually date.

  • Asking in person: When possible, this is the best way to ask by far because seeing the person face-to-face gives you the most information. You can read body language and see whether the potential date looks pleased, terrified, God-forbid-revolted, or delighted.

    Based on the other person’s reaction, you can then modify your behavior accordingly or run. The disadvantage with asking in person is that it’s also the scariest for the exact same reasons. But it’s still preferred and also the friendliest technique.

  • Asking on the phone: This method gives you less information, but if you get panicky, you can always hang up before they answer (although caller ID has made hanging up without saying anything a great deal trickier). When you ask over the phone, nobody can see your palms sweating; but then again, you also can’t see your potential date’s reaction.

    Never ask an answering machine for a date. It’s cowardly, sends the wrong message (you’re manipulating them by making them call back before you ask them out), and occasionally, the machine actually eats the message. You never know if your potential date got the message or if it was intercepted by a protective parent, a jealous ex, a careless roommate, or the Fates.

  • Asking through a third party: In elementary school, you may have asked your best friend to ask her best friend if someone liked you. You may have even eventually gotten an answer, but after Suzy told Peter, and Peter told you, were you really 100 percent sure about the answer? Third parties are a very unreliable method of information flow.

    Remember the story of our Pilgrim forefathers, John Alden and Miles Standish? Miles was the governor who asked his best friend John to intercede on his behalf with Priscilla Mullens. Priscilla decided she liked the messenger, and Miles was left out in the cold. Don’t ask somebody else to ask for your date. The messenger may end up taking your potential date, and then not only do you still need a date but you also need a new friend.

  • Asking with a note: Even though computers have made notes faster and sexier, notes don’t offer you much information and feedback, whether they’re e-mail or snail mail (through the post office).

    When you ask with a note, you also don’t know the mood your potential date may be in. In addition, a note opens the opportunity for interception, misinterpretation, a delay in feedback, and a lack of flexibility. Ask anybody who’s asked for an RSVP to a written invitation, and you begin to understand the problem with asking for a date through a note.

    If you’re absolutely determined to ask for a date in writing, send a handwritten note via the post office, because it’s classier and implies more effort and concern.

    A brief note here on sending a note with flowers, cigars, wine, a baseball hat, a ticket, or any gift: Sending gifts with the note is cute but tricky. You don’t want to appear to be bribing your potential date on the first date.

    Gifts can be a token of respect and admiration and are okay and even valuable as you’re getting to know each other, but they can be too much too soon. Besides, you don’t want to have to top yourself later and end up buying your potential date a small country by the fourth date. Start out simply.

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