Methods for sending the message

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.

The breakfast of ex-companions

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.

When other people get involved, sometimes they add their two cents to your message. For example, what if your best friend liked me and wanted you to ask me if I’d go out on a date with him? Can you see lots of room for sabotage and miscommunication?

Avoiding Certain Places Like the Plague

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

Friends, relatives, and — believe it or not — exes

If you’re absolutely determined to ask for a date in writing, I suggest 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.

Getting an Answer

Okey, dokey — you’ve made plans, offered options, and asked for a date. Now what? Well, either the answer is yes, you have a date, or no, you don’t.

If the answer is yes, you’re flying and ready to go on to planning the old date-aroony

Dealing with a no

If the answer is no, you have nothing to lose by asking if another day, place, time, or event would suit them. Listen to the response carefully. Often people really are tied up working late, taking care of a sick parent, getting out of a
relationship, studying, or being distracted and would be willing to consider an invitation in the future, just not now.

If you’re feeling brave, you can say, “If not now, how soon?” If you’re feeling a bit vulnerable, you can say, “Let me give you my number, and you can give me a call when you’re ready.” The middle ground is to say, “Why don’t I give you a holler in a week or two and see how you’re doing?” If your potential date says fine, then do it. If he or she says “I’ll call you,” don’t hold your breath. Who needs to turn blue?

Getting some feedback

If you get a no, you may want to take a minute to try to figure out why. Make sure you haven’t gotten into some bad habits. You may need to ask yourself some tough questions. Are you too eager, too desperate, too whiny, too silly,
or too tense? Is your breath okay? Do you make eye contact?

No matter how honest you think you are, give yourself some balance by asking a willing friend to critique your approach (you’ve seen it in a million movies where the hero or heroine practices in front of a mirror — no, not Travis
Bickle’s “You looking’ at me?” line). Balance your friend’s feedback with your own opinion so that you’re not being too easy or too harsh on yourself.

The personals: Online and off

If you mess up your careful scenario, your friend can give you some tips and hints on improving it, and you can make sense of what you meant to say or do. Practicing can help you get a grip on your nerves. A little nervousness is flattering to the potential date because it shows that you really want to get to know him or her. Too much nervousness can panic both of you.

All things considered, it’s probably even better to be a little bit nervous than so nonchalant and cool that your potential date has the sense you couldn’t care less if he or she accepts your invitation or not, because if he or she isn’t interested, no biggie, it’s not them, you’ll just move on to someone else. It’s not a terrible idea to start a first date on an honest basis. I know — don’t tell anybody I told you, and we’ll try to keep it our dirty little secret.