There are two different ways of asking someone out on a date. The first is simply to indicate that you’d like to hang out: “We should get together sometime.” This is a good lead-in for getting someone’s number in order to call him or her up for a date—“Is it okay if I call you?” The second way to ask someone out is to do it directly: “Would you like to have dinner with me Friday night?”
When you call to ask someone out, always have a plan in mind, even if it’s a spur-of-the-moment suggestion to go grab a bite. If it’s someone you’re really interested in, try to have a real invitation ready, including a specific activity (tailored to the other person’s interests, if possible) and time frame.
The Good “Ask”
A good “ask” would go something like this:
Tom: "I'm great. How 'bout you?"
Elise: "I'm good, too. Listen, I was wondering if you'd like to go to dinner at that new Thai restaurant on Saturday. I know you've been wanting to try it ever since it opened."
Regardless of whether Tom says yes or no, Elise has just executed a terrific ask. In two sentences, showing both consideration and confidence, she’s suggested a date and a place and indicated that she had considered Tom’s interests and tastes. Whether they’re just friends or she’s asking him out on a first date or they’ve been dating for some time, she did it right.
If the ask results in a “Yeah, sure,” this is the time to establish where and when you’re going to meet. Later, after Elise makes the dinner reservation, she’ll need to call Tom back and fill him in on other details, such as appropriate attire and whether she plans to take him to a movie or some other entertainment before or after dinner. (Elise can also send her the details by email, but a phone call is more personal—and isn’t that what dating is all about? Besides, with email, if the other person doesn’t check their in-box frequently, your message could go unread for some time.)
The Bad “Ask”
An “ask” that is too vague or open-ended comes across as a lack of confidence and consideration. Here’s what not to do:
Tom: "Not much. And you?"
Elise: "Oh, the usual. Um, so, do you want to go to dinner or something sometime?"
Tom: "Um... sure." (It's such a vague offer, it's hard for him to respond with much enthusiasm.)
Elise: "Great! Where do you want to go?"
Tom: "I don't know. Where do you like to eat?" (He's surprised that she doesn't even have a place in mind- and so, being unsure himself, he throws the question back at her.)
Elise: Anything's good with me. What are you in the mood for?"
Meanwhile, Tom is wondering how he’s supposed to get excited about a rendezvous he hasn’t actually been asked out on yet! It’s been about two minutes now, and our girl still hasn’t pinned down a date and time, let alone a place. By now, it’s pretty obvious she hasn’t thought of any agenda that would encourage Tom to want to go out to eat with her. In fact, she’s basically put the ball in his court by expecting him to plan out their entire date.
When in Doubt, Ask
If you’re worried about what your date would prefer in a given situation, ask before you act:
"Would you like a drink or just some wine?"
"Can I get your chair for you?"
"Ooh, that entrée does sound good; when the waiter comes over, would you like me to order that for you?"
"Do you want to wait here while I go get the car?"