First things first: the biggest piece of dating advice anyone can give you is this—don’t meticulously plan out your first dates, because the best experiences are often the ones that genuinely surprise you and push you out of your comfort zone. That said, if you’re cycling through dates without forming much of a connection, dating experts suggest injecting more creativity into the questions you ask on a first date.
It might be time to change your language. Instead of the usual, tired go-to questions (What do you do? Where are you from? etc.), try something new. Why? “Asking great questions on a date can give you a lot of insight about the person sitting across from you,” Sarah Patt, a matchmaker and dating expert, tells Bustle. “By the end of the date, you want to be able to know if you connect with the person and whether or not you share similar lifestyles and values. Asking great questions will help determine if this person has what you are looking for in a partner so you can decide if their world is one you want to know more about, or become a part of.”
So, if you’re stuck trying to come up with killer questions that lead to killer dates (and maybe even a relationship?), here are some great starting points:
1. “What Was Your Family Like Growing Up? Got Any Fun Stories?”
Patt says that if you feel comfortable bringing up your date’s family history, the answers can reveal a lot. “If they are talking openly about their family, it suggests they have strong relationships with their parents and siblings,” she says. “This will give you a glimpse into their childhood and upbringing.”
The important thing to remember is that no one gets to pick the family they are born into (or seriously, wouldn’t you have chosen someone famous as your relative?). So, try not to judge them too harshly on the details. Instead, focus on what truly matters to your compatibility: Do you care if their parents are divorced? If they are an only child, is that an issue if you come from a large family?
2. “How Would Your Friends Describe You?”
Even if someone is outgoing and friendly, they might find it difficult to talk about themselves directly. Relationship expert Dr. Karin Anderson Abrell tells Bustle that instead of asking direct questions, bring a third party into the equation. “Asking them what their friends say about them provides them the safety of describing themselves from another person’s point of view,” she says. “In addition, you get to learn about their friendships—which, of course, ultimately says a lot about who they are.”
3. “What’s a Hobby You’ve Always Loved?”
Similar to asking, “What do you like to do for fun?”, this question reveals what your date does to unwind and de-stress. Life coach Kristy De Leon tells Bustle it also offers insight into their social circle. And perhaps most critically, it lets you know if your interests are compatible.
“People typically spend time with others who are similar to themselves, so if you start hearing about activities that you would never, ever do, that’s a big warning sign,” she says. “If the person says that they don’t have anything fun they like to do, that’s also a significant red flag. It means that they haven’t developed themselves enough to know what they enjoy. There isn’t even a mental seed planted about self-care.”
4. “What’s the Best Vacation You’ve Ever Taken?”
“The answer to this question will give you an idea of your date’s sense of adventure and what they consider to be standard for a ‘great’ experience,” Patt says. If they mention their favorite trip was skydiving in New Zealand, Patt says they are likely spontaneous and love thrills. Conversely, if their preferred vacation involves relaxing on a beach with unlimited drinks, they might have a more laid-back personality. “Ask a follow-up question like, ‘What’s your ideal vacation?’ to ensure you have an accurate picture before drawing conclusions,” Patt adds.
5. “Who Is Your Least Favorite Celebrity?”
The goal of a date is to get to know someone, yes, but also to have fun. Dr. Abrell says a question like this is amusing but will also help you learn something important about each other. “Knowing what people dislike can be just as informative as learning what they do like,” she says. Bonus points if you both name the same one.
6. “If You Could Have Any Superpower, What Would It Be?”
Would they choose to fly? Be invisible? Eat anything without gaining weight? Read minds? “When asking a lighthearted, playful question, you’ll not only get a good idea of their humorous side, but you’ll also have a better understanding of their character,” Patt notes. Consider the magical strength they select: if they want to fly, they might need to release stress or possess great curiosity; if they want to read minds, they may be more analytical.
7. “Do You Like What You Do for a Living?”
What’s more revealing than asking what someone does between 9 and 5 each day? Asking if they actually enjoy those hours. “This question is truly telling about the person’s ambition toward their future. If their answers are uncertain and lack clarity, that is a red flag. This may mean they are becoming complacent and satisfied with settling for whatever happens to come their way,” De Leon says. “We’ve all had jobs that were stepping stones, but that is exactly what they were—we knew going into the job that it served the purpose of a stepping stone. It wasn’t a forever job. If a person is complacent about their own future, then they will likely have this outlook toward other areas of their life.”
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