Richmond Proper: On Asking for a Date

With Valentine’s Day getting close, doubtless some of you are starting to sweat because you don’t have a date. Before the panic sets in, recognize these two facts: (1) you don’t *have* to get a date to enjoy Valentine’s Day — in theory it has just as much to do with freedom as it does with romantic love, and (2) asking someone out on a date is a simple and relatively painless procedure.

February 9, 2010; 6:00 AM • by Tess Shebaylo

“All it takes is courage, self-confidence, and practice. While it’s true that whoever does the asking runs the risk of rejection, it’s also true that being too afraid to ask may cause you to miss out on many of life’s pleasures.”

— Nancy Tuckerman and Nancy Dunnan, The Amy Vanderbilt Complete Book of Etiquette

With Valentine’s Day getting ominously close, doubtless some of you are starting to sweat because you don’t have a date. Before the panic sets in, recognize these two facts: (1) you don’t have to get a date to enjoy Valentine’s Day — in theory it has just as much to do with freedom as it does with romantic love, and (2) asking someone out on a date is a simple and relatively painless procedure.

Fact #1 we won’t spend too much time on, because as much as I might forget it, this isn’t history class. But the truth is, this holiday doesn’t just belong to those in love. The origins of St. Valentine’s Day are in celebrating a saint martyred by Rome for trying to preserve his way of life in arenas possibly connected to romance, which is something we can all understand. So think of this day as the state of Virginia: it’s for lovers, but not exclusively.  Everybody else tends to enjoy the heck out of it, too. You can have a great time on Valentine’s Day without a date by organizing a hangout for fellow singletons complete with all the pink frosted confections you can manage to eat.

To arrive at Fact #2, we must deconstruct the stigma that surrounds asking for a date. Being our own worst critics, we think that a rejection means we’re unattractive, uninteresting, and unwanted. We blow these assumptions up until they are giants looming over us, preventing us from making date invitations. In reality, it is not that bleak. Remember that the world is not necessarily stocked full of other beings whose purpose is to scoff at you, and that it may actually be full of people trying humbly to make their way in the world, too. If you ask someone out there’s a good chance that he might say no, but even if he does, what have you lost? All that this person has done is say that he does not wish to accompany you to such-and-such a place at such-and-such a time. He is not decreeing that you be banished from society. And of course, if you ask someone out there is also a good chance that she might say yes. Which brings us to some things we should remember in order to — we hope! — make this happen.

• Don’t wait until the last minute. In all the teen movies, by the time the guy has mustered up enough courage to ask the girl to prom, she’s already got a date. It turns out her schedule isn’t as wide-open as he would like to think it is. Don’t let this happen to you! As Peggy Post says, “It’s courteous to extend invitations as far in advance as possible. A day or two ahead is okay for casual dates, but be aware that last-minute invitations may be perceived as insults.”
• Choose your venue wisely. Though in-person is the agreed-upon standard, don’t rule out other methods of getting in touch. If your love is always on the go and on the phone, you may have to call him just to make sure you’ll reach him. And if the girl you adore is a tech maven, it might be a good idea to send her a quick IM or email instead of waiting for that perfect moment to pop up IRL.
• Don’t use some contrived pick-up line. “Pickups, to seem respectable, must be contrived to seem accidental,” says Judith Martin. The perfect way to alienate a stranger is to use some cheesy pick-up line to get her attention. Rather than making her feel special, a boilerplate, pre-conceived speech can make her feel like a faceless item on an assembly line stretching into infinity. If the object of your affection is someone you don’t know but would like to know, find a better way to start a conversation.  “Hello, I’m ___. Can I buy you a drink?” is a good start compared to the cringe-worthy “Come here often?”
• Be direct. If you wait until the end of a conversation to ask someone out, you’ll probably end up talking yourself out of it, or worse, seem like you’re reluctant to spit the question out. “The best way for a man or woman to ask someone out is with a clear plan in mind. Present it up-front,” says Judith Martin.
• Be specific. “Flabby, half-hearted, indecisive invitations should never be issued,” says Judith Martin, and she suggests an equally vague response: “Reply to ‘Do you want to do something sometime?’ by saying sweetly, ‘In theory.'” Everybody knows that when two people agree to “hang out sometime,” it barely ever happens. To get the date-asking process started, make specific plans for a specific time and place. If other suggestions are made, you can still be flexible of course.
• Know when to give up and when not to give up. Peggy Post advises, “Be attuned to the person’s attitude and tone. An astute observer of social cues often gets a sense of whether the person would like another opportunity to go out; if you sense real interest, try again later.” It might be the case that he’s just busy this Friday night, but would really like to hang out with you on Saturday instead. Or he might never want to hang out, and you should get the hint and stop asking. Learn how to tell the difference.

I’m sure we have plenty of readers who have more experience than I do with asking people out. Please comment if you have some tried-and-true suggestions to offer up to the greater good!

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