Five Questions To Ask On A First Date That Will Guarantee A Second
There’s a fine line between fizzing chemistry and tumbleweed awkwardness on a first date. You’ve gone through all the usual first-date questions that are basically adult version of ASL (age? sex? location?) from university, but if you really want to make a connection then you need to be asking the right questions.
Relationship therapist Megan Bearce says if the goal of a first date is to see if there’s possibility there, a well-informed Q&A is the quickest way to form a bond. “Asking questions conveys that you have an interest in them and not just a date where all you do is talk about yourself,” she says. “You may find out that there are major differences you have on certain topics, and even if you’re physically attracted to them, knowing this early on can help figure out where it’s going.”
Memorise the expert-approved questions below. The answers will help you gauge compatibility and set sparks flying.
“What was the best trip you’ve ever been on?”
Chances are, everyone has been somewhere that meant a lot to them. Travel is a topic that connects people and it’s not too personal that it feels invasive. “This kind of question can help you determine how adventurous your date is, both as a traveller and in their life. Do they like the unknown? Do they like trying new things? This question will answer it,” Bearce says. Listen to how they describe their trip, too, she says: “You could learn they liked the fancy hotel, room service and shopping, where you’re more of an outdoors or camping person, which could be a clue that there are some differences.” If they mention, and can laugh about, mishaps during traveling – missed flights, language barriers, unexpected delays – it might signify they’re willing to tackle challenges head-on.
“If you had the day off tomorrow, what would you do?”
When you’re working 9-5 (or 7 or 8), it can be easy to get wrapped up in your never-ending to-do list instead of thinking about what you would do if you didn’t have to log in so many hours. It’s likely your date feels the same way and hardly even imagines what she would do if she didn’t have to go into work the next day. Founder of the Professional Wingman, Thomas Edwards says that creativity in your questions can take your conversation from dull to awesome instantly. “Get specific but let them have the chance to elaborate and tell a story – that’s when you’ll really get to know them,” Edwards says. This question will reveal if they’d love to sleep in, have a long lunch or brunch, or if they’d do something spontaneous like take a day-trip to another city nearby. Whatever it is, it’ll give you a view into how they like to spend their downtime and if that’s something that matches with your taste, too. It also lets you spitball ideas for date number two.
“I have another wedding next weekend – seems like everyone is getting married! Are all your friends getting hitched, too?”
It might seem like a red flag to bring up marriage on a first date, but sex and relationship therapist Dr Kat Van Kirk says an indirect reference will help you detect her feelings toward her friends, family and future. “You can often make conclusions about what she wants out of life by discussing the people she is the closest to,” she says. “Asking a benign question about whether her family lives nearby can also be a great way to pick up on how she handles those relationships and if she has outstanding issues.” Pay special attention to how she describes her friends – is she catty and dismissive or doting on them? – because this is likely how she’ll discuss you in the future.
“Do you have a pet?”
Bearce says this question can lead to all sorts of conversations, including about her childhood and any experiences with animals. Look for opportunities to bring it up organically – like you’re walking by a dog on the street. “If you are an animal lover, this is great information and can also give you indirect insight into their personality,” Bearce says. Another vital piece of info you’ll glean here is whether she’s on the same side of the great Dogs vs Cats as you. (For reference, dogs win every time.)
“What’s the most exciting thing you have coming up?”
Edwards says by asking what’s ahead in their life and why it’s getting them amped up, you’ll see the things that matter to them. They could mention a big presentation, a fun trip, reuniting with a family member or doing something special for a friend. Whatever it is, the insight into their internal countdown will give you some clues on what this person is really like. It also gives you an opportunity to talk about the things that you have going on and why they’re special to you – seeing how she reacts to them will give you some idea of whether she’ll be there with you.