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5 Perfect Questions to Ask on a Date

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Want to know the best questions to ask on a date? Here are five date questions that you can add into your conversation to find out if you’re compatible with each other.

date questions | questions to ask on a date

First dates can be exciting, and yet, a bit jittery, what with all the list of date questions everyone’s armed with these days!

As much as a date is about questioning and interrogating each other, it’s also a lot more about keeping the conversation going and having a great time.

Here are five questions to ask on a date that can make the difference between a happy future and a wasted date.

Why we need date questions

Over the years, all of us have had dates and have had to face a barrage of questions ranging from the mundane to the obnoxious!

Some date questions are just plain stupid like “what would you do if you win a million dollars?” and some date questions like “what are you looking at, right now?” crosses privacy into ridiculousness.

Now don’t get us wrong, they’re not bad questions. It makes your date feel like they’re being judged in a job interview. And no one likes that!

[Read: What to wear on a date]

Questions to ask on a date

If you want a long list of questions to ask on a date, well, you’re just sad. Dates don’t work that way! Dates are special, and each date is as unique as the two unique individuals on the date.

While we are going to give you a list of date questions you can ask, you should remember that these date questions can help you gauge a potential future. You can’t use a list of 25 questions to ask on a date and drone on like a old broken record.

If you really want to know the questions to ask on a date, and have a charming, gushing conversation that can carry on for hours, read these two tips. It’s got everything any man or woman would ever need to carry on a conversation on a date.

[Read: What to talk about on a first date]

[Read: Six great conversation starters]

The five date questions

Once you’ve read those two links we’ve given above, you would be a sophisticated, smooth talker who can charm any date in no time, we assure you!

If you’re having a great time on a date, everything can seem happy and nice. But how can you judge if your date is a long term potential? That’s where these five questions to ask on a date come into play. [Read: Places to go on a first date]

Depending on the way your date answers these five questions, you can have an idea about them and find out if they’re what you’re looking for.

Question #1 Do you enjoy your work?

Pop this question in while you’re speaking about your date’s work. How does your date answer to this question?

In life, we all face a lot of hurdles and difficulties. And we have two kinds of people, the whiners and the doers. Whiners whine about everything, and yet do nothing about it. While the doers, obviously do something about it.

If your date whines about their job, who’s to say they won’t whine about your relationship in the later years? This questions can help you understand what kind of a person your date is, and how they cope with difficult issues in their life.

Question #2 What do you do when you’re having a tough day?

You see, these are simple questions and you’re not going to put your date in a spot by asking these questions. And yet, they can reveal so much about their life and their attitude towards it.

Every now and then, we all have to deal with shitty days, let’s face it. But how does your date cope with it? Does your date jog the frustration off, watch a few movies at night, order a big take out, or do they like to lock themselves up and spend some time alone, contemplating *plotting revenge* about it?

So if you both ever hook up, are you both going to deal with the difficulties in life together or will your partner just withdraw into a shell?

Question #3 How long has it been since your last relationship?

In any other circumstance, this question would be personal. But both of you are meeting up to see if there’s a chance to be together. So in this case, this is a good question to ask on a date.

This date question can help you gauge if your date is looking for true love or a rebound relationship. And even if we’re not talking about a rebound relationship, it could tell a lot about your date’s view on life.

Let’s face it, many of us love drama in our lives. Some of us just can’t be happy when things are all pleasant and smooth in love. We need a roller coaster ride of frustration and intense happiness to keep the excitement alive in love. And if we’re not getting it, we break up and move on to experience it all, all over again! So how’s your date here?

Question #4 How long was your longest relationship?

This is a date question that can help you understand your date’s approach to life. Long term relationships are no joke, to be quite honest. It takes a lot of love, determination and compromise to keep the boat of love from rocking.

And sadly, many people just don’t have what it takes. They care too much about themselves to put up with someone else, even if it’s a lover. And they can’t really change their ways too. If your date’s had no long term relationship over at least a year, then something’s not usually right.

Yeah, there’s also a chance that they haven’t met anyone who’s really nice and sweet. But still, a series of short relationships should have a red light flashing.

On the other hand, if your date’s been in a very long term relationship for several years or a decade, it can be difficult to erase those old thoughts away and they may need some time to actually move on or forget about their ex.

Question #5 What do you do on weekends?

A very simple question to ask on a date, but one that is very revealing.

Weekends are that time of the week when you don’t have to work or worry about anything, and it’s all about doing what you like. It’s that time when you indulge in activities that really give you joy. So what does your date like doing on weekends?

Does your date’s activity define them or make them more interesting? Is it compatible with your interests?

Hanging out in unwashed boxers and playing a game on the PlayStation, or spending a whole day on facials and massages can seem like fun to many, but what about you? Getting this compatibility wrong will lead to a very frustrating love life.

[Read: How to get a guy to like you]

[Read: How to get a girl to like you]

And there we have it, the date questions that can make or break a date. Remember, a happy date isn’t about reciting a list of questions to ask on a date, it’s about having a great conversation with each other, and falling in love with each other. Of course, that’s after you’ve snuck these five questions into the conversation!


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Have your say!
  • Maria Jacobs
    November 10, 2011 | Permalink |

    You know what, I’ve never actually used even one of these questions on any of my dates! I’m shocked.

    I do speak about work, but about the other stuff, I’ve always assumed it’s personal for a first date. But coming to think of it, it’s actually not very intrusive and yet quite revealing.

    I think a few other nice questions to ask would be,

    1. Why did you break up with your ex?
    2. What interested you about me?
    3. What kind of a relationship are you interested in?
    4. What kind of muic do you listen to?

    I’m sure these questions would help understand the compatibility better too.

  • Temperance
    December 12, 2012 | Permalink |

    I really like this article! The other day, I was telling a friend that a person’s beliefs and the way they approach situations is the most important thing to judge when looking for love. My example was how they treat people or how they want to raise their kids.

    My ex and I love all the same TV shows, a lot of the same music, enjoy the same video games (our Facebook “likes” pages are very similar”), but we completely disagree on how treat people (I’m politically correct, he likes to call people names), care for ourselves (I eat healthy and organic food, take vitamins, etc, whereas he eats junk and doesn’t work out at all), what values are important to teach children (in my opinion, honesty, assertiveness, confidence, he thinks they should be “badass”) and so on. That’s why things didn’t work out.

    I’m not a pro at first date talk, though, so asking “how do you plan on raising your future children?” probably isn’t a good idea!

  • Ed
    January 11, 2013 | Permalink |

    I’m not very successful with dating but I’d assume that askng questions about an ex or a previous relationship would be a terrible idea. Sure, scientifically, you can discover facts about what they might be like as a partner, but emotionally you can bring up all sorts of monsters and heartbreak. Plus it’ll make you both even more likely to compare/ your date with previous partners rather than taking them for who they are.

    These are just my ideas though. I might easily be wrong as I’ve not had many successful dates.

  • JessiJ
    January 12, 2013 | Permalink |

    I cannot agree with #4. Sorry, but I haven’t been a long term relationship at all. Simply because I was constantly traveling for school, and came from a very sheltered family. I’m learning, and I would love to be in a long term relationship, but I think it’s ridiculous for anyone to decide not to give someone a go if they’ve never experienced a long term relationship yet are more than dedicated to being in one. How would I be able to even get a long term relationship if the guys judge and dump me upon hearing that I’ve never been in one? Everyone starts somewhere, and some are late bloomers, and I am one of them.
    Upon reading this though, I would never want to discuss that on a first date. And if you tell me I will be judged, then I guess I will have to lie.

  • t blinks
    January 2, 2014 | Permalink |

    U guys r doin a great job but i have a question. Wat am i 2 do if d gal i was askin out sudenly showed up and said it over bcos she was back wit her ex

  • Rick
    July 23, 2014 | Permalink |

    Asking about past relationships, or the time elapsed since the most recent relationship are TERRIBLE questions. Especially in the beginning. Sorry but this is bad advice.

    And Maria, don’t ask why the person broke up with their ex either! Instead, ask what you looking for a new relationship.

    I have literally never had a date that ended with the woman not wanted to see me again. Trust me or not, but everyone reading this, do yourselves a favor, disregard this article and be yourself. The best version of yourself, but don’t ask a bunch of textbook questions!

    I wish I had more hands, so I could give this article three thumbs down!!!

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