10 Insightful Questions To Get To Really Know Someone On A Date

There is only so much you can gather about someone while on a date, so you have to make it worthwhile. Asking all of the right questions can be helpful for getting to know your date better. 

Dating around can be strenuous. This strain is mainly because you can waste plenty of time with someone on multiple dates before you actually get to know them. Unfortunately, we all have to do it. 

While getting to know someone new can be time-consuming, you can make it effective from the first date. Read more to discover ten insightful questions that will help you get to know someone while you’re on a date. 

One Question 

Photo by Priscilla Du Preez on Unsplash

Asking your date what one question they wish more people asked them will let you in on their passions. The open-ended approach is excellent for helping people get out of their shells and talk about things they enjoy. 


Paulette Wooten on Unsplash

Getting to know when your date last got excited and why will also help you dig deeper. You will get to know more about the things that make your date happy and see if you have anything in common. 

Red Flag Detector

Damir Spanic on Unsplash

Ask your date what their family and friends would think if they got arrested for ruling out any serious events. On the other hand, this question can end up being great comedic relief during your date, depending on the answer. 

Like A Movie

Photo by Alex Litvin on Unsplash

Many people don’t realize how exciting they are until they shift their perspective. Get your date to open up a bit more about themselves by asking them what scene they’d replay over again if their life were a movie. 

Compatibility Test

Photo by JESHOOTS.COM on Unsplash

According to marriage and family therapist Kati Marquez Meyers, people who love scary movies are compatible. Ask your date what their thoughts are on scary movies to see whether you are a good fit. 


Benjamin Wedemeyer on Unsplash

If you are trying to dig into your date’s innermost desires, ask them which parts of their life they feel something is missing. This will encourage them to self-reflect and possibly become vulnerable about things. 


Photo by Darius Bashar on Unsplash

Spending time on dates with someone who isn’t ready for something new can be disappointing. To avoid this, ask your date if they consider themselves healed from the situations that hurt them in the past. 

Making The Bed

Sinitta Leunen on Unsplash

Ask your date whether they make their bed every morning to discern their level of discipline and organization. This can also be a great way to determine whether someone is a morning person or not. 


Sincerely Media on Unsplash

People’s social lives and priorities can be deal-breakers in relationships, so figure them out first. You can achieve this by asking your date how they spend their weekends, which will let you know everything. 

Coping Mechanisms

Sydney Sims on Unsplash

Everybody has different coping mechanisms, but some can be harmful to others. Gauge how your date deals with challenges by asking them what a telltale sign of them being stressed is that nobody else would know.

Written by:
Siba Mosana

Recommended Posts