Questions to Ask on a First Date
They can be pretty awkward, especially if you’re meeting someone you barely know, or if you’re just naturally shy. First dates get the best of your nerves, especially if you don't know how to steer the conversation.
Imagine sitting through a meal with a stranger, with questions in your head like:
a) is there any chemistry between the both of you?
b) is there something you are both extremely incompatible about?, and
c) if you like them, can you score a second date?
Yes, first dates can be pretty nerve-wracking. This is why our Date Coaches are here to help ease your anxiety, and provide you with tips and guidelines on how to ace that first date.
If you’re unsure what to talk to your date about, here are 4 main phases of your first date to look out for, and the questions that you can ask in each phase. Happy dating!
First Phase: When You First Meet Up
- Thanks for taking the time to meet me! Was it easy for you to get here, or have you been here before?
Why: By showing that you appreciate the other party for making the effort to come to the date, you will make them feel like they have made the right decision, as well as feeling good.
- How is your day so far?
Why: This question helps establish if your date is a positive or negative person. He or she could start talking about the good parts of their day, or they complain about everything that went wrong.
Additionally, if anything has happened in their life recently that might have affected their mood in a negative manner, it’s always good to have a heads up before the date.
- Is there anything that you don't eat?
Why: This gives you an idea of where to go for future dates. It is also an opportunity to find out if you have similar or drastically different food preferences. It also shows that you are a caring person if you make the effort to remember their preferences.
- You have a very interesting *insert something that caught your eye, e.g. tie, earrings*, where did you get that?
Why: Everybody likes to be complimented. It also shows that you are an attentive person, and is an easy conversation starter.
Second Phase: During the Date
- Have you travelled anywhere recently? What kind of holidays do you usually take?
Why: Holidays are always a good topic to start with, as it’s lighthearted. You can also see if you are compatible in this aspect by listening if their answers match with your preferences. One of you may prefer backpacking trips, while the other prefers leisure trips.
- What do you like to do when you are not working?
Why: This question helps you establish your date’s attitude to life. For example, are they a workaholic with career goals, or are they someone who prefers a lifestyle that balances both work and life well?
- Have you seen any movie/ TV shows/ art shows recently?
Have you been to any good restaurants recently?
Why: These questions show if your date is open to trying new experiences. It’s also a great way for you to get some second date ideas!
- Are you an only child?
Do you have siblings?
How many people are there in your family?
Why: Knowing how your date feels about their family is a good way to tell how they’ll approach their own relationship. Is his or her family dynamics something that appeals to you?
- How do you feel about *insert something that you are really into e.g. swimming, hiking*?
Why: It’s fairly important that couples have similar interests in order to strengthen the relationship. However, it is fine to have little similarity as well, as long as you know they respect what you are passionate about.
- Are you a dog person, a cat person, or neither?
Why: If you are a major animal lover and your date has zero interest in animals, that is most likely going to be an issue in the long run.
- Are you a morning or a night person?
Why: While seemingly a light-hearted question, it can tell you a lot about your date. Imagine, for example, if your date drags you out for a morning hike when you are a night owl. That might be a potential issue in your relationship!
Third Phase: When the Date is Ending (and you want to keep it going!)
- Would you like to go for dessert? I know of a good place nearby.
Would you like to get a drink? There is a great place just around the corner.
Why: To prolong your date, you can always suggest desserts and drinks. You can also use this to gauge if your date is interested in you or not.
Do take note that this can be a bit tricky if you do not know the area well. Do your preparation beforehand by Googling the area and reading the reviews, so that you don’t unknowingly take your date to a bad place.
Fourth Phase: Scoring a Second Date
- You mentioned that you were interested in this *place, movie, restaurant*. Would you like to check it out together this weekend?
Why: When you bring up a place your date mentioned in passing, it shows that you were truly listening, and are genuinely interested in getting to know them better. Additionally, if it’s something that the other party enjoys, it is less likely for them to turn down the date. Hopefully, this will get you that second date!
Do note that these questions are merely to serve as a guide. You do not need use all of them, or follow the guide strictly on your first dates.
If your date has questions for you, answer them, and go with the flow of the conversation. The above questions will be useful when you’re not quite sure what to talk about!
Importantly, do prepare your own answers for the questions above for first dates or any after that. Be willing to share information about yourself, and do not just expect the other party to keep answering. Remember, it's a date, not an interview.