How Did Your Date Go? Use The Test of 5 Questions

This guy knows how his date went. Not well.

Some dates are easy to evaluate. Fall asleep in your bowl of spaghetti, and then wake up to discover your wallet’s gone? It’s pretty clear how that date went. Go home at the end of the night wearing someone else’s underwear? Again, not hard to deduce the quality of your evening. You may want to rethink some personal choices, but all in all, you probably had a pretty good date. Or a very very bad one. But most Internet encounters are not so clear cut. A lot of them, in my experience, are…pretty good. Not great. Not terrible. But pretty good. You laughed a little, drank a little, nobody lost an eye – it was an entirely fine evening. But you’re not sure if you want to repeat it. So what do you do? Do you ask them out again and see if there’s more of a spark, or do you cut bait and search for someone else to trade underwear with? A lot of you have been doing neither. You’ve just been emailing me, and asking what I think you should do. And what do I suggest? I suggest you use The Test of 5 Questions.

The test of 5 Questions is incredibly simple, and honestly, I use it myself all the time. Here we go – get out your pencils, because it’s about to get complicated. Should you see your date again? The only thing you need to know is: did they ask you 5 questions? That’s it. Pretty simple. I don’t care about if they’re an Aries or a Cancer, if they smiled when you touched their arm, or if they smelled like pineapples and morning dew. Did they ask five questions, in total, by the end of the night? That’s all I want to know. If they asked you five questions — what you thought about politics, or where you like to go drinking, or what you think the Oompa Loompas smelled like — any quandaries at all, then you’ve got yourself a keeper. Because five questions means they’re genuinely trying to know you. They want to know what you think, who you are, what, essentially, is your deal. And someone who cares about your deal is a lot rarer than you think.

Oprah always asks 5 Questions

You’re probably thinking, “Come on, five questions? That’s really all it takes?” Well, five questions is actually quite a lot. Since I devised this little technique, I’ve been keeping track, and easily half of the women I’ve met don’t ask five things about me. There’s always plenty to discuss, there certainly aren’t any silences, it’s just that everything’s about them. And I don’t care. In fact, I’m happy to learn about them, it’s what I’m on the date for. I don’t need to hear my stories, I’ve heard ‘em, they’re pretty much all about my cat. But when I realize my date doesn’t wanna hear ‘em either, that’s when I know we’ve got a problem. Because no logical person is gonna go out with a stranger and not try to learn everything they can. They could be a murderer, or a religious fundamentalist, or, you know, your future husband. And if you don’t wanna know which one of these is me, chances are the reason is you don’t particularly care. (Answer: They’re all me. Yippee!)

Here’s another way to think about it, in case surreptitiously counting off questions on your fingers isn’t your idea of a good time. Could your date write a paragraph about you when the evening concludes? If he or she can’t, then they’re really not trying to date. There could be a million good reasons – they get nervous, they start talking and get caught up with the story, they’re so eager to make a good impression they forget to give and take. All fair, all understandable, and if you like a person, I think it’s great to give them a second shot. But if someone doesn’t want to know enough about you to fill a third of a page, why do you want to know anything about them? Even if hanging with them was a pretty good time?

Look, some dates have their own flow. A night can take off and the chat gets so great that you finish and find you have no idea how you got where you are. That date is a success, and the Test of 5 Questions isn’t for you. But if you’ve just had a hug and a peck on the cheek and wondered, “what exactly happened back there?”, then the 5 Q’s may be the answer you need. Try it. Then email me and tell me how you did.

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6 Responses to How Did Your Date Go? Use The Test of 5 Questions

  1. Elizabeth says:

    Ah, but what about the guy who asked me 5 awkwardly pre-prepared questions (“So what’s the craziest thing you’ve done in New York?”) so then I felt like I had no choice to finish each of my answers with “So how about you?” and then listen to his 5 pre-prepared anecdotes? A for effort, I guess.

    Or the guy who managed to ask me 5 questions between responding to texts/answering phone calls/eventually bailing early with a promise that he’d make it up to me, which of course went unfulfilled?

    THE SYSTEM IS FLAWED.

    • B says:

      The test is only meant for in-betweeners, Elizabeth. If you know a guy’s a dud, don’t use the 5 Questions, they won’t help. They’re all for the tough-to-figure cases. Break the Question glass in case of emergency only…

  2. Datinator says:

    I ended my most recent Match date a couple of weeks ago trying to remember of she asked a single question about me. She did ask me in initial texting what my profession was.

    B, would it be a mitigating factor if I told you she may be the most beautiful girl I ever went on a date with? If so, would the fact that she is an illegal alien stripper who drank about 7 glasses of wine be of any relevance?

    Before you answer, remember, she’s like a 9.8 on the hotness meter.

  3. Paula says:

    I like this a lot, though I sort of think if you’re spending time wondering if you should see someone again the answer is no. Every time I’ve been unsure, or second-guessed myself (“re-evaluated”), it’s always been a mistake, if not a disaster. You KNOW if you like someone, you do not have to wonder about it. You’re excited about the idea of being with them again… the time can’t pass fast enough. Anyway, this one guy I spend a couple years with was always asking a lot of questions, seemed so interested in me… but he never remembered anything I said.

  4. Susan says:

    This a very brilliant and simple idea. One of my biggest pet peeves is self-absorbed people, who don’t recognize that a conversation involves give and take, aka listening and asking questions. I always screened my dates on the phone before committing to meeting them, because I could learn a lot about them in 20 minutes over the phone (and not have to shower and put make up on first!). Usually I would ask a few simple questions, such as what did you do today (“bought towels with my son” was one response, very exciting) to “where do you like to go out in Chicago” to start the conversation flowing. I have been stunned by the men who just start rambling… and I let them. I find it amusing, maybe it’s not fair, but I just sit back and wait for them to say “oh, enough about me, what about you”? Maybe this isn’t fair of me, but life isn’t fair, is it? I broke this rule once or twice and went out with someone who was self-absorbed and not a good conversationalist on the phone only to find them the same in person. I have had men tell me in great detail on the first phone call about their obscure hobbies, professional successes, marathon training schedules, etc. I listen, ask questions (“really, you run and swim the same day?”) and wait, and wait, for them to ask me a question. Sometimes, when they come up for air, they’ll say, so should we get together for a drink? And I’ll say, no thank you, it was nice talking to you and good luck. Isn’t that the point of talking on the phone before you make plans to meet? LIfe is short, so don’t spend it on a bad date when you could have figured that out in 15 minutes on the phone.

  5. Jen says:

    Okay, thank you for this! My sister recently set me up with this guy, and I don’t think it’s going to work out but couldn’t really pinpoint why. He was handsome, interesting, and nice. We went to a bar one night and a music festival the next day, and they were both fun, but it was just a little off. After thinking about it, I think this was the issue… after hanging out for extended periods on two separate occasions, I still don’t think he asked me 5 questions the whole time… not even “what about you?” after I’d ask him something.

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