The 7 Best Questions To Ask On A First Date

by Lindsay Tigar

First things first — the biggest piece of dating advice anyone could give you is this: don’t plan out your first dates because the best experiences are the ones that surprise you and put you out of your comfort zone. That being said, if you’re going on a ton of first dates without much success or connection, dating experts recommend putting a little more creativity into the questions you ask on a first date.

it may be time to change your language. Instead of the ole’ go-tos: What do you do? Where are you from? etc. Why? “Asking great questions on a date can give you a lot of insight about the person sitting across from you,” Sarah Patt, 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 at a loss for what to stay to really stir up killer questions that lead to killer dates (and maybe a relationship?) — here are starters:

1. "What Was Your Family Like Growing Up? Any Fun Stories?"

Patt says if you feel comfortable enough on your first date about their family history, it can tell you a lot. “If they are talking about their family, it shows they have great relationships with their parents and siblings,” she says. “This will give you a glimpse into their childhood and upbringing.”

The thing to remember here is that no one gets to pick the family their born into (or um, wouldn’t you have picked Queen Elizabeth as your grandma?) — so don’t judge them too harshly on what they tell you. Instead, consider what matters to you in compatibility: do you care if their parents are separated? If they’re an only child, is that a dealbreaker if you come from a big family?

2. "How Would Your Friends Describe You?"

Even if someone is outgoing and friendly, they may not find it easy to talk about themselves. Relationship expert, Dr. Karin Anderson Abrell, tells Bustle instead of asking direct questions about them, put someone else 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 Enjoyed?"

Similar to ‘What do you like to do for fun?’, this question will show the things that your date does to blow off steam. Life coach Kristy De Leon tells Bustle it’ll give you a glimpse into their social circle too. And maybe most importantly, it’ll let you know if your interests are compatible.

“People typically hang out with people who are similar to themselves, so if you start hearing of activities that you would never ever do then that is a big warning sign,” she says. “If the person says that they don't have anything fun they like to do, that is also a big warning sign. It means that they haven't developed themselves enough to know what they like or really enjoy. There is not even a mental seed planted on 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 great or standard,” Patt says. If they mention their favorite vacation was skydiving in New Zealand, Patt says they likely love thrills and are pretty spontaneous. But on the other hand, if their favorite type of vacation is relaxing on a beach with endless drinks, they might be more low key with a relaxed personality. “Ask a follow-up question ‘What’s your ideal vacation?’ to make sure you have an accurate picture before coming to any conclusions,” Patt adds.

5. "Who Is Your Least Favorite Celebrity?"

The point of a date is sure, to get to know someone, but to also have some fun. Dr. Abrell says a question like this one is funny but will also help you learn something about one another. “Knowing what people like can be just as informative as learning what they do like,” she says. Bonus points if you both say the same one.

6. "If You Could Have Any Superpower What Would It Be?"

Would they want to fly? Be invisible? Eat whatever they want and never gain any weight, ever? Be a mind reader? “When asking a lighthearted, playful questions, 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 what magical strength they select: if they want to fly, they likely need to release stress or are curious, if they want to read minds, they may be more analytical.

7. "Do You Like What You Do?"

What’s more telling than asking what someone does 9-6 each day? Asking if they actually enjoy what they’re doing in those hours. “This question is really telling about the person's ambition towards their future. If their answers are uncertain and without clarity, that is a red flag. This may mean they are becoming complacent and ‘OK’ with settling with anything that happens to come their way,” De Leon says. “We all had jobs that were stepping stones, but that is just it — we knew going into the job that it was serving the purpose of a stepping stone. It wasn't a forever job. If a person is complacent towards their own future, then they will have this outlook towards the other areas of their life.”

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