psychology Mandy Kloppers

Important questions to ask on a first date

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When you go on a first date, you’ll probably feel a mixture of excitement and nervousness. You hope that you will get on with this potential romantic partner and you also hope that you will make a good first impression and that they will like you. From the very beginning, you will both be learning about each other to find out whether you are compatible. This is why there are important questions to ask on a first date.

There are questions that are more likely to help you figure out how compatible you really are. We can all use extra help when we meet someone for the first time.

I’ve put together a useful list of important questions to ask on a first date:

How long have you been single?

The answer to this question can tell you a lot about a person. If they haven’t been single long they may have trouble being alone. It’s usually (not always – there are always exceptions to the rule) a sign that this person might be getting into a realtionship for the wrong reasons. For example – they may be dating to give their self esteem a boost. This strategy is fraught with danger.

When you rely on external sources to help you feel good about yourself, you will constantly feel insecure. Your feeling of self esteem will be fleeting until you receive the next reassurance from someone else. In a way, feeling good about yourself is taken away from you and put into the hands of others – why would you want to rely on others for such a fundamentally important and integral part of your character, being and personality?

If they have been single for a very long time (more than three years), this could signal a fear of intimacy. people who have been on their own for a long time tend to become set in their ways and use rigid thinking. As in – something is good or bad with very little inbetween. I have noticed these patterns in the numerous clients I have met over the years.

Healthy dating usually occurs between 6 months after a relationship ended up to three years.

How do/did you get on with your parents?

You can tell a lot about a man by the way he treats his mother. If he is respectful and thoughtful where she is concerned, he will most likely treat you the same way. If he has no time for his mother and resents having to see her, it’s highly likely that he will be selfish and treat your needs as secondary. Again, this is a generalisation but I have seen this pattern surface numerous times over the years that I have practised as a mental health therapist.

Women that have good relationships with their fatehr will be more likely to have a secure attachment with less ‘hang ups’ than someone who had a father who was distant or selfish in some way.

The attachments you form with your parents as a child influence your adult attachments. If you had a loving relationship with your parents that was safe, stable and secure, you learn that the world will generally meet your needs. Your foundations for going forth romantically are healthy. If however, your relationship with your parents as a child was inconsistent, neglectful or even abusive, you learn that others won’t always meet your need and you will learn coping mechanisms to protect yourself from the hurt others might inflict. As a result, your brain will develop on a way that can creat barriers and limit your success in adult relationships. If your parents were critical or offered conditional love (for example – you only felt valued if you were getting good grades in school) you may develop perfectionistic tendencies in an attempt to be good enough for your parent’s love. Our relationship with our parents has a huge impact upon our romantic relationships as adults.

What do you enjoy doing in your spare time?

You’ll want to know if you have much in common and knowing more about the other person’s habits will help you to figure out how compatible you are. Do you both enjoy lying in bed in the mornings? is one of you sporty whilst the other one isn’t? They say that opposites attract but research has shown that those with more in common stand a better chance of longevity. Some differences are good but not fundamental ones where your values clash.

Small differences that aren’t important include, for example, what type of food you like to eat, your film and music preferences. These are less significant and can be overcome with good communication and compromise. Differences that may be more significant include your religious and cultural backgrounds. How you would want to raise children (or even have a family in the first place) and values such as honesty, trust and commitment.

What do you think about …?

Choose your own topic here but make it about something that you have a strong opinion on. This isn’t intended to start an arguement – remember you are just getting to know this person. If you feel strongly about something that happened recently in the news, it might be a good idea to see if they are aware of the story and what their thoughts are on it. Try not to be judgemental, instead use this question to find out information about this person. You can often glean a substantial amouont of information byt asking them their opinion on something. Often, you will get insight into their reasoning and what’s important to them (possibly some more values will be revealed here too).

Who do you admire?

This question can help you understand the other person’s goals and ambitions. If they admire someone like Nelson Mandela that could tell you a lot about how they feel about justice and perseverance. If they admire Tom Cruise, they may be someone that wants to be wealthy or popular.


Why is a great word. It helps you understand the machinations of another person’s brain. When we ask “why” we get to know someone far quicker. It helps you to figure out how they see the world and how they make sense of the world. You could ask them why they got into a specific profession or why they didn’t. You could ask why they like travelling or don’t particularly like ripped jeans. This clever little word opens up the other person’s personal encyclopedia. Be careful not to ask too many “why” questions or the other person may feel like they are attending an interview. Ask with genuine curiosity and have fun with it. You don’t have to take this first date stuff too seriously.

Other behaviours to watch for:

Do they ask much about you or talk only about themselves? If they spend most of the time talking about themselves and rarely ask you anything it might be a sign that they are quite selfish and self absorbed. Sometimes though, this can be due to being nervous on a first date so you’ll have to decide which one it is.

Do they consider your needs and feelings? Again, it’s a good indication of how much emotional intelligence and empathy someone has if they are attentive to your needs.

How do they treat the restaurant/bar staff? Someone who is rude to waiting staff might end up being an aggressive perosn who is hard to please. Again, this isn’t always the case, especially if waiting staff have been rude or unprofessional.

Do they seem to have many friends? – be wary of someone who has no friends (unless they are new to the area). People who have had friends that they have known for a long time tend to be genuine, warm and empathic. You need to have these traits to sustain longterm friendships.

The above should act as guidelines when you are on a first date. Use your common sense and intuition to help you decide whether this new person might be compatible with you. If you can’t decide, have a second date. What have you got to lose? Dating is a numbers game, the more you date, the more likely you are to find someone that matches you. Don’t take it too seriously and don’t take it personally if someone rejects you. At this stage of the game they hardly know you. I believe there is someone out there for all of us, it’s just a matter of finding them.

Mandy X





Photo by Huy Phan on Unsplash

Mandy Kloppers
Author: Mandy Kloppers

Mandy is a qualified therapist who treats depression, anxiety, OCD, PTSD, trauma, and many other types of mental health issues. She provides online therapy around the world for those needing support and also provides relationship counselling.