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10 Best Questions to Ask on a First Date

I enjoy exploring the unknown and the boundaries of love and life.

Know the best questions to ask on a first date.

Know the best questions to ask on a first date.

First dates can be nerve-racking. Perhaps you’ve been chatting casually on a dating app or decided to meet the person you’ve been talking toand think that your connection could really blossom and turn into something. Now it’s time to figure out what to talk about on your date. It’s always important to keep a first date casual and to keep the conversation flowing as this time is about seeing if you have chemistry, but what is the best way to really make sure you two are compatible?

What Questions Should You Ask on a First Date?

To help you out on your love adventure and to find out if your love will truly blossom, learn how to ask these 10 leading questions. By not asking your date questions directly, you are more likely to receive a truthful answer. These 10 questions are sure to encourage great conversation on a first date and will help you to learn more about your love interest.

1. What is something you’re proud of?

Ask your first date what they are proud of in their lifetime:

  • What is one of the most fulfilling activities that you do in life?
  • What’s something that means a lot to you?
  • What is an activity that brings you joy?
  • Who do you look up to?
  • What inspired you to follow the path that you’re on?

Some of your date’s answers might include work, church, loving their pet, art, meditation, socializing and going out, reading, and even winning awards in work, sports, or philanthropy. Maybe your date is someone who runs a non-profit, donates money regularly for a cause, or attends weekly beach cleanups...they may even reply that they’re proud of their son or daughter if they have kids. Whatever their accomplishments or passions are, you are sure to get a good sense of their values and get an idea of what they do in their precious free time by asking this leading questions.

2. What does a typical day look like for you?

Ask your date what their day-to-day looks like. Find out if they like to wake up early during the weekday and sleep in or if they like to go out and stay out late bar-hopping. They may be more of a homebody, a workaholic, or live a sober life and attend church regularly - it’s good to find out what they’re all about.

Do Your Lifestyles Match?

Perhaps they stay in on the weekends and read, watch movies, or binge on Netflix. It’s important to get a sense of their lifestyle so that you can tell if you are compatible long-term in a serious relationship. You may find that your typical weekday or weekend may not blend well with theirs and it’s better to find out sooner than later.

Find out which questions help to break the ice on a first date.

Find out which questions help to break the ice on a first date.

3. What is the worst first date you have been on?

Asking your love interest about the worst date they’ve ever been on will tell you a lot aboutt them. This is a bold question and a funny one at that which can help break the ice on a first date. If your date seems to be going well and the chemistry is on, consider asking them about the worst first date they’ve been on. This way, you can find out what exactly they are looking for in a potential partner. Did they get Catfished? Were they lied to about something major? Do they hate certain personalities and quirks, like louds laughs, timidness, etc.? Do they hate people who are always tardy or treat employees - like servers - rude at restaurants? A person’s pet peeves can tell you a lot about them.

4. If you could get any advice from anyone alive or dead, who would it be?

Ask your date who they would go to for advice. This question is a deep one and it will definitely score you some smart points. Once the conversation gets comfortable, consider tossing this question out there.

Who Is Your Date Inspired By?

When asking who it is, remind your date that this can be anyone (dead or alive). Some common answers might be Albert Einstein, Oprah, Carl Sagan, Jesus, or the Dhali Lama. This type of question offers a look into who your date values as a person and where their life views are drawn from.

5. What would be a perfect day for you?

To get a good sense of how your date would like to spend their time in an ideal situation, ask them what their perfect day would look like. This will help you to find out, once again, what they value or what aspirations and dreams they may be aiming for in life. They may be the type of person that truly loves to have an action-packed, adventurous day. Or, their ideal day may involve peace and quiet and relaxation. Perhaps they are a foodie and enjoy going for good eats. Maybe they attend church and love to meditate or pray. You may find that they like to go for a good nature walk, or going out and drinking with friends is more their jive.

What His Answer Means

This type of question will give you a good read of your date and will help you to determine if your likes or dislikes are similar. If you are more into nature walks, and they are more about going out and tasting food and then meeting up with friends to stay out drinking, you may find that your core interests do not align.

6. What is the funniest joke you have heard?

Does your date have a good sense of humor? Ask your date to deliver their best joke. This will help you to gauge if your sense of humor is similar to theirs. Gauging their humor will help you to see where their head is at - literally. Perhaps they are all about the sexual jokes, and that’s simply not your style. Or, they may tell a joke that would be considered offensive - this will help you to look for red flags.

7. What is your favorite thing about your best friend?

To dig a little deeper, ask your date about their best friend and their best friend’s attributes. Ask them what their favorite thing about this special person is. A question like this will give you some insight into what they value most about someone near and dear to them. It will also help you to understand if the two of you are compatible long-term should you pursue a relationship.

If your date tells you that their best friend is always the life of the party, always doing ridiculous things and getting in trouble with the law and they think that type of behavior is funny, you may actually find it obnoxious and intolerable. But if you find out that their best friend is all about resilience, lifting other people up when they are down, and lending a helping hand, then you may find that you and your date’s values align.

Ask leading questions to get a sense of your date’s values.

Ask leading questions to get a sense of your date’s values.

8. If you won the lottery, what would you do with the money?

Asking a question about winning the lottery is sure to be a fun conversation point for dreamers. This question also lets you figure out what type of approach your potential boyfriend will take to their finances. After all, money is a huge point of contention with most couples. Ask your date what they would do if they won the lottery. If they say they’d go out and buy three ferraris, three houses, and a yacht, that might sound impulsive to you. Perhaps they say they would invest all the money and live frugally, but that might not resonate with you either. This is a great question for learning whether your financial goals are similar depending on if they would spend, save, invest, or do something philanthropic with their wealth.

Ask your date something deep so that you can develop your connection.

Ask your date something deep so that you can develop your connection.

9. What is the most embarrassing thing that has happened to you?

Ask them what the most embarrassing thing is that has ever happened to them. If your date really digs deep and share something truly outrageous, that may help to draw you closer. You may find that they are embarrassed of something you tend to brush off or work past, or maybe they describe something minor that you feel most people should be able to process. Their answer to this question will give you a sense of their maturity as well. You may also find out if they are easily embarrassed and what to do and what not to do around them.

10. What is the best advice you’ve ever received?

This question is another mature and insightful one that will definitely score you some thoughtfulness points on your first date. Ask your date what the best advice is that they’ve ever received. Their answer to this question may help you to paint a picture of what their life has been like. Perhaps they went through a major struggle and someone told them something to uplift them. The advice they received may be around money, spirituality, patience, forgiveness, bravery, etc. This question is also a great opener for digging deeper into their psyche and really getting to know them on a personal level.

This content reflects the personal opinions of the author. It is accurate and true to the best of the author’s knowledge and should not be substituted for impartial fact or advice in legal, political, or personal matters.

© 2020 Brynn B Lewis


dashingscorpio from Chicago on September 30, 2020:

Good questions!

The mistake a lot of people make is creating an "interrogation" atmosphere rather than getting the other person to relax.

Some people even ask why their date's last relationship failed. Talking about failed relationships and exes doesn't make for a great date. The whole purpose of a (first date) is to find out if you are compatible and have chemistry.

Dating is supposed to be a (fun) sociable activity!

Generally speaking you want to keep things light and relaxing. Ironically people also tend to reveal more about themselves when they don't feel like they're on the "hot seat".

Secondly if someone is "into you" or "thinks you're hot" they are doing to do their best to say or do whatever they believe want to hear or see from someone you'd consider dating.

Therefore asking too many serious questions early on is a waste of time. If they pass the compatibility and chemistry test you'll have plenty of opportunity to get into more details on future dates.

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