5 Unexpected Questions You Should Ask On The First Date 

Girl on bad date


Going on a first-date is nerve-racking as it is, especially when you’re trying to figure out what to talk about. You want the conversation to flow smoothly and having a few conversation starters in your back pocket can reduce your chances of a lull in the convo.

Having a couple of questions to ask your date when the conversation starts to lag is great arsenal to have just in case, but what kind of questions should you be asking once you find out each other’s favorite color and what their hobbies are?

As it turns out, during a first-date, taking some time to ask deeper, thought-provoking questions actually allow for you to go deeper and learn as much as you can about your date. By asking more personal questions, you not only get the answers you need, but your date will feel more connected to you because you stepped outside of the box and asked questions to get to know them better rather than asking generic, baseless questions. Asking questions that are thought-provoking and more personal helps build a connection quicker.

If you’re looking to get down to things right away and get to know who your date really is, take a look at these 5 unexpected questions to ask on the first-date.

1. How’s Your Relationship With Your Parents?

Boy and his mother


You can tell a lot about a person by their relationship with their parents so listen to your date’s answer to this question carefully. Knowing that your date has a close and personal bond with their parents can be comforting to hear and lets you know that they are very family oriented. If your date’s parents are no longer around, be sensitive to that and don’t probe or push for more answers if they aren’t forthcoming.

Also, if your date isn’t as close to their parents or don’t speak highly of their parents, be careful not to judge them for their relationship and don’t be quick to cast them off. While this is a great question that allows for you to get to know a person better, this shouldn’t be the only question/answer you’re using to get a better idea of who your date is either.

2. If You Could Have Any One Superpower, What Would It Be?

Superheroes party theme halloween


Trading superpower stories is a fun and silly way to get to know your date’s innermost thoughts. Do they want a superpower that allows them to help others or is their power more focused on helping themselves? Do they want a superpower that is generic or is their superpower unique and creative?

Asking this question allows you to see how your date handles thought-provoking questions and if they are good at conversing. Do they take their time and put some effort into their answer or do they give you short responses? Make a note of how your date answers silly questions, which will provide you with clues on how they’ll respond to serious questions as well.

After you both are done trading superpower stories, a good follow up question is to ask your date who their favorite superhero and why. A good follow up question helps keep the convo going, and your date engaged.

3. What Was The Best Vacation You’ve Ever Been On?

Woman Traveller


Asking your date their favorite vacation may be a little weird but it’s also very telling. Your date’s answer to this question will give you a better idea of your their sense of adventure and what they consider great or standard.

4. What Are You Looking For?


Alright. Let’s be real here. No matter how you ask it, this questions will always be awkward to ask and is just downright uncomfortable. But, if you really want to know what your date is looking for and want to be on the same page, asking what they’re looking for is unavoidable.

Sure it makes things awkward at first, and your date may squirm, but it’s better to ask now and make sure you and your date are on the same page versus later down the line.

5. What Are Your Thoughts On Monogamy?

cheating couple


The worst thing you can do on first-date is assuming, especially when it comes to questions like this. Again, you want to make sure that you and your date are on the same page so asking questions like these, help you get a better gauge on how you and your partner feel about things like commitment in relationships. Ask this question early to avoid finding out down the line that your bae is really a swinger or casual serial dater.

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