Never ask for a first date for Friday or Saturday night

When asking for a date, having a plan is crucial, but you’ve got to stay a little loose. The more structured you are, the more dependent you are on meshing well with a stranger. Therefore, you need to read the signs, stay loose, and keep things light, flexible, and open. You can seriously improve the chances of getting a yes if you keep these tips in mind when you ask for a date.

Improving Your Odds

These two main, big, serious date nights are too important a place to start. Asking for a first date on a Friday or Saturday is like playing at Wimbledon without a tennis lesson or having ever played on grass or at all. Even people who
don’t have dates and haven’t had one for ages are often loathe to admit their plight to a stranger (and if you haven’t had a first date, you’re still strangers).

Start off with a Wednesday or Thursday night, which are nights when people generally don’t have much planned. Also avoid Mondays like the plague. Everybody hates Mondays.

Never say, “Would you like to go out sometime?”

If you phrase the invitation like this and the askee says “no,” you’ve left yourself absolutely no out except to be swallowed up by a prayed-for earthquake. If the person says “yes,” you still have to ask him or her out. Yikes.

Instead, be specific. It’s much better to say, “I’d love to see the new exhibit at the museum. Any interest in going either Wednesday or Thursday?” You offer a specific opportunity (as well as alternative days) and at the same time, you
give your potential date a great deal of room in which to negotiate without sounding wishy-washy or desperate. Giving specifics also allows your potential date a couple of seconds to think about it, rather than getting caught completely off guard.

Always offer options about the date

Options can include the day, time, activity, and transportation. Options make you sound organized without being bossy or rigid, as long as you keep them limited. Offering a few choices at the outset makes you sound less panicky
than you would if you were to offer them after the potential date says no to your initial suggestion.


If you’re specific about the date and your potential date doesn’t like the suggested activity but does like you, you can modify your plan. Also, although a plan with several separate possibilities requires more work on your part, it offers a better chance of success — and a chance to figure out whether your potential date has any interest in you. After all, if you’ve offered all options regarding place, time, date, activity, and so on and the answer is still no, the problem is as clear as the writing on the wall, and you’ve hit the wall. Take a deep breath and move on. It’s not the end of the world, just this potential date. Scary but efficient.

The Invitation: Sending the Message

By offering to meet there, go in separate cars, or pick her up, you instantly show yourself to be considerate, capable, and sensitive to the fact that females have heard horror stories about being abducted by a date and never seen again.
Although you’re not Jack the Ripper, understanding that she may feel a little uneasy about being in a car with a stranger makes you a liberated and cool guy for thinking like a modern woman. You will score major points.

In the initial stages of dating, people sometimes want so much to be liked that they agree to things at the expense of their integrity. If your potential date has enough sense to say, “I’d love to do something with you, just not mud wrestling,” then give that person a gold star. Don’t be offended — be pleased. You have just found someone with brains, courage, and honesty.

Remember that timing is everything

Don’t ask for tomorrow or next year. A basic rule is to ask for a first date a week to ten days in advance, but you can break this rule with impunity as the need arises. You can ignore these guidelines if the spirit moves you to be spontaneous. For example, “Hey, got time for an ice cream cone?” can get you an immediate yes; you can also expand this invitation to a “maybe next week”

if you get a no. Now is always a better time to ask than later because your courage may diminish over time. There are some obvious exceptions to this rule: Don’t ask someone who is in a crisis (never ask for a date at a funeral), just getting out of a relationship (never ask for a date at a divorce hearing, even if the person isn’t one of the parties involved; it’s bad karma), or going through any other experience when you may appear to be exploiting a weakness. You need to take the other person’s life situation into account as well.

Always go for it if you’re having a good hair or anything else day

You’re cuter when you’re happy, and self-confidence is sexy. Don’t get into the “well, today is a write-off, I may as well ask, get rejected, and make it a perfect score” mentality. You can tolerate being turned down more easily when you’re feeling strong — not to mention that rejection is a lot less likely.

Asking someone out for a first date isn’t the time to trot out your best anything, including your imagination, checkbook, or best friend. This is a time to think KISS: Keep it Simple, Sweetie. All you want to do here is send a clear and gentle but important message: I’d like to spend some time getting to know you better. Are you interested?