First Date Conversations: Gentlemen Edition!

Happy asian couple

You arrived at the first date, nervous and full of jitters. As the man, you faced the extra pressure of being the one leading the conversation on the first date with a lady. Your mind is filled with questions like what to say or what to do to create the best first impression on the lady.

We understand all your concerns and worries. Therefore, our team here at Fabrique has compiled a list of tips and topics for you to ace that first date with good conversational skills (or at least give the impression of being one).

Do Your Homework

man lazing and lying over the kitchen counter

If you want to ace that paper in school, what do you do? You do homework. Yes that’s right! To ace a conversation with the girl of your dreams, do extensive research on broad topics or recent happenings as well. A well learned person (or so it seems) creates a better impression on the lady. If you are aware of the lady’s interests or hobbies, read up more on what interests her, so that you have something meaningful or interesting to contribute.

Safe Zones

Stamp of Approval

So, now that you have done your homework, you must be wondering which topics belong to the safe zone. Find out more below:


Singapore is a food paradise, so ask her if she has visited the coolest or latest cafe in town, or recommend this great zi char place that you know (or whatever cuisine interests her). You can seize the chance to ask her out again to visit the place that interest her the most!

Movies/Dramas/Variety Shows

It could be the most recent blockbuster that you have watched or she has watched. It could also be the latest episode of Korean Variety Show that interest her. Getting her to talk about what interests her is a good way to engage her and to know her preferences as well. At least you know what to suggest for the next movie date!

Travel Experiences

Everyone has been bitten by the travel bug with the increase ease and convenience to get around on budget carriers. Travel experiences are good avenues to break the ice even further, by discussing about countries that both of you have been before, or asking her about a country that she has travelled to but you have not etc. Ask her for her recommendations, her experiences, her itinerary or even what interesting foods she tried over in the other country.


Work forms a huge part of our lives, so it is inevitable that during the date, you would have mentioned the industry or company that both of you are in. However, the topic need not be mundane, as you can take the chance to turn it into a very interesting conversational topic. For example, if you are working in pest control, you can share fun facts about the commonly found insects or pests. Find something witty and interesting about your work or industry to talk about, but do not go into anything which are sensitive, or turn it into a complaint session about your colleagues/company.


Interests and hobbies are also good topics to break the ice further, as sharing about what interests you or her naturally gets you or her talking passionately. Suggest to try out an activity or hobby which she is interested in, and most likely she will be more than willing to include you in, which scores you another chance to ask her out again.

Taboo Topics


Since there are topics in the safe zones, naturally there are topics which are dangerous to go into on a first date. As a general guideline, do not talk about your aspirations towards marriage, your future wife or kids.  This is a first date, so however much you want to share your ideals towards a happy family life, keep these topics to yourself until both of you are ready to take the next step. Not talking about the future does not translate into talking about the past either, so talking about ex-girlfriends/wives is definitely a no-no, as it gives the impression that you have not moved on from the past relationships. Sensitive topics like politics or religions are also best avoided on the first date, as you do not want to turn a first date into a heated debate over differing opinions.

Ask, Ask and Ask More Questions

Ask more questions

If you have been reading up till now, you would have noticed an obvious trend by now in the points discussed above, which is to ask, ask and ask more questions. Ask open ended questions where you can get her to share more, rather than “Yes” or “No” questions where it is harder for you to continue with the topic or conversation. Keep the questions light and interesting, as this is not a job interview after all!


Attentive Listening

This may seem to contradict the current topic discussed since it is about talking and conversations, but listening to the lady is one of the key things to show that you are genuinely interested in what she is saying, and responding appropriately to what she has said are important elements to carry a good conversation. After all, conversations require two-way communication!

Awkward Silence?

Awakward Silence

Awkward silences are hard to avoid at certain pauses during the course of the conversation, or in between transit to another topic. Diffuse the situation by acknowledging it, laugh about it and use the chance to share your funny stories about other situations of awkward silences.

We hope the 6 tips above will help you plan your first date conversations better! If you have other tips to share with us and others, write in to us here! At the same time, check out some of our dating events for singles!