The questions to ask and topics to discuss on a first date, according to relationship experts

While some individuals have mastered the art of the first date, for many of us, the meetings are frequently fraught with sweaty palms, nervousness and stilted conversation.

Fortunately, according to relationship experts, there are some tried and true methods for ensuring that a first date conversation goes smoothly, regardless of whether you feel a spark or ultimately decide to end the date as friends.

To find out what topics to discuss and what questions to ask on a first date, we spoke to relationship expert and best-selling author Susan Winter and Relationship Hero coach Shoya Arriana, who shared their advice for increasing chances of scintillating conversations and connections.

According to Winter, one of the most important things to remember with first dates is that they should be about having fun and getting to know an individual in a “light-hearted manner,” which means that at no point should it feel as if you, or your date, are on a job interview.

However, she also notes that the type of first date you have will depend on what you are looking for, whether it be a relationship or something more casual.

For those who are looking for a partner they can get serious with, a category of individuals she describes as “intentional daters,” Winter first advises not bothering with suitors who are not looking for the same, noting: “Intentional daters shouldn’t waste time on window shoppers.”

Arriana reiterated the sentiment, telling us: “You should assess whether or not this person has the same dating goals you have, and should not walk away from that date not knowing whether or not they’re dating casually - as in just looking to meet people and have a good time, or dating intentionally - as in they’re interested in finding someone to build something with.

“Even if you feel like you and someone had amazing chemistry, if their goals conflict with your own? You risk wasting your time and getting hurt unnecessarily.”

Once you have confirmed that a date is looking for the same thing, Winter suggests spending a first meeting gauging such things as the person’s disposition, as well as how you feel in their presence.

“Gauge the person’s disposition by observing their warmth and openness, while also observing how you feel in their presence,” she said, adding that topics helpful for this purpose can be hobbies, travelling, work, pets, music, or anything that provides an “initial connection”.

According to Arriana, it is also generally useful to avoid topics you are unfamiliar with, as it can increase nervousness in individuals who are already feeling first-date jitters.

Rather, she suggests focusing on topics you’re “already well-versed in,” which can more easily result in a conversation you are comfortable in, as well as a connection.

“My suggestion is to invest curiosity into things you’re already well versed in to see if it’s something they’re also into or interested in because, if you can create a conversation about something you’re already well versed in, not only do you create an opportunity for both of you to be more comfortable, you also increase your chances at connecting,” she explained.

However, if you and your date have established that you are both just looking for fun, Winter said the first date requires less-specific conversation about goals and values, telling us that it can instead focus on “attraction, chemistry and flirtation”.

“This first date conversation can be fluid as expectations are low and have less concern for heartache. You’re trying to see if hanging out with this person will be a fun fit for you,” she explained.

As for questions intentional daters should be asking first dates, Winter told us that these individuals are advised to broadly inquire whether their date is “open to the possibility of a relationship”.

“This is a generic, not specific, question. You’re not asking them to be in a relationship with you. You’re asking ‘why’ they’re dating. What’s the desired outcome? This is an important time-saver,” Winter said.

According to Arriana, how your date answers questions about what they are looking for should be indicative of whether there will be another date, with the relationship expert noting you can also phrase the question as: “So what brings you on the dating scene?” or “I’m curious what your dating goals are?”

“If your dating goals conflict? I suggest having a good time but perhaps not pursuing another date,” she told us, adding that it can also be useful to ask when their last relationship was, as it can reveal any potential risk of becoming a rebound.

Apart from questions intended to find out what your date is looking for romantically, Arriana suggests asking about their passions, their career and their pastimes, and what they get out of these activities, as the questions can help “assess what a person’s values are”.

“For example, if someone is in the [armed forces] and says that they are from a family of service men and women? You can safely assume they value loyalty and tradition. If someone works in sales or even in the arts? I’d be willing to bet they value independence highly and have a curiosity towards people in general,” Arriana said.

For casual daters, first date questions can lean more to the fun, flirtatious side, with Winter telling us that individuals can ask about anything from hobbies to how their date likes to spend their weekends.

“‘Do you have a favourite city? What’s your favourite type of music? What’s the thing that people rarely get right about you in the first meeting?’ These are all standard questions that should feel comfortable to speak as well as receive,” Winter said.

And, according to Arriana, if you prepared your questions in advance, it is also worth thinking about your own responses, as chances are you will be asked the same questions by your date in return.

“Be prepared to have answers to the questions you ask, as more than likely they’ll be reciprocated,” she said, adding: “If everything checks out? I also highly suggest not letting that first date end without you at the very least attempting to suggest a second date.”

This article was originally published in July 2021.