Dating 101: First-Date Questions

This entire post is for people who are single and trying to date people.  Or people who are just curious about what it’s like to be a single dude trying to get to know a girl.  Here are some hard-learned statistics from the dating world.  This lesson is sponsored by awkward first interactions and hyper-observation, and is about…asking questions.

Before we get started, this is meant to be read with the understanding that you can’t end any of the questions with creeper statements.  Examples are provided below.

For the most part, it’s generally ok to ask questions that start with the word “What” or “Have you.”

“What do you do for a living?”  “Have you ever been outside of the country?”  Surface stuff like that.

Same with “Have” questions.  Again, these questions can’t be followed by creeper endings like, “What’s the freakest thing you’ve ever done” or like “Have you ever been so hungover that the next morning, you poop and puke at the same time?”  One, these questions make it seem like you’ve done stuff like that before.  If you haven’t then why would you be asking the question?  Two, if you’re asking those questions, it either means you’re really drunk, or don’t care about seeing that person ever again.  Or a combination of both.  Either way, if you’re asking these questions, it’s not making for a good first impression.

“Do” questions usually are ok too.  “Do you like Harry Potter?”  “Where” and “When” are pretty neutral, asked sparingly.  These kind of questions asked too frequently make you sound like a cereal killer or a stalker.  But those are typically second-tiered questions.  “Have you ever traveled outside of the country? When?”

But the absolute off-limits questions are ones that begin with “Why”.  “Why did you get into that?”  “Why do you like that?”  Depending on the topic, these questions are often digging into something personal.  The answer to these questions don’t deal with surface material, but rather, the reason or motivation behind those actions.  And for the most part, people will be generally honest about the answer.  But therein lies the rub.

A lot of times, people aren’t used to being asked these questions.  They are questions that they might not have even asked themselves.  And if you ask a question that makes them wonder why they are doing something in the first place, it can bring up an insecurity.  It takes a very confident person to talk about personal discoveries or the reason behind their actions.  Asking these questions makes you a great friend in an intimate setting over wine, but not on a first date over kamikazes and lemon drops.

“How” can be a good advancing question when used in the right spots.  The hard part is determining where those spots are, so be careful.  Again, could be too personal.

Here’s the breakdown of types of questions to ask, ordered by safety level with a corresponding percentage.

What – 80%
Have – 75%
Do – 60%
When/Where – 58% (I just picked some random, semi-neutral number)
How – 50% (half good and the other are half bad)
Why – 10%

In a lot of instances, second-tiered questions that advance an initial question can be risky.  Same with questions about family, religion and political issues.  But honestly, if you end up asking a lot of questions like this, then the other person is either not interesting or not interested.  Or a combination of both.  The most constructive conversations are ones that resemble a tennis match.  You serve up a question, and they respond.  Then, before the convo loses steam, you volley back with a statement that either answers the initial question you just asked or add to the response that they just gave.  Don’t serve up aces, and don’t dominate the conversation.  The last thing a girl wants to see is a returned volley and then you take the ball, do a couple of tricks with it, motion to the crowd, and then look for applause.  Girls are impressed by the conversation, not how you are the coolest person ever.  And girls like to talk; typically twice as much as guys.  However, the conversation shouldn’t be 70% of them answering questions and 30% you asking.  It should be an even match, filled with give and take.  And if she starts asking questions back, then you’re doing something semi-right.

And when I say that you’re doing something semi-right, it could mean that you have no chance at all.  The problem with some girls is that they don’t know how to end conversations without seeming like a big bitch, which makes no sense at all.  But I can guarantee every guy would rather hear “Well, it was nice to meet you, have a good night,” then lead them on the entire night thinking they have a chance.  There is nothing wrong with telling some guy politely that there is no way anything could happen.  If you say, “See ya,” and they ask for your number, just decline or say you don’t think it’s appropriate.  If they’re a creep and won’t let you go, then just walk away.  Who cares.  If nothing is going to happen, don’t let them think something will by entertaining their conversation.  I’m not endorsing bitchiness by any means.  I’m saying to be aware of when to use it, how and to who.  Creeps and freaks are going to continue to be themselves regardless of how they make you feel, so don’t feel like it’s inappropriate to pull out the “I’m Not Interested” Card.

Guys have a 3-minute investment level.  A guy will invest 3 minutes, and then if he sees he’s getting a return, then he’ll keep going with the intent of getting a number or getting…something else.  3 minutes: that’s all it takes for a guy to become interested and eager.  Play within the timeframe, ladies.

Maybe this is all BS.  In either case, you probably shouldn’t be taking advice from a single guy who spends most of his time striking out with girls at bars.  This is just works for me.  Or, I guess, doesn’t work.  But the overall keypoint is this:

Guys: Don’t be a creep and keep to the surface
Ladies: Politely end conversations when it’s a deadend.

Thanks for reading.

-The Ladies Man



  1. That diary image is awesome. It kind of broke the “blog bro code” by not attributing the content to my blog though. I mean…it was obviously inspired by me…

    Btw, I’m a cereal misspeller…

Leave a Reply

Your email address will not be published. Required fields are marked *