The Questions I Always Ask on My First-Dates

I’m sure everyone agrees with me on this, but I do not like to waste time- especially when dating. Money you can earn back, but time you cannot- and this is why I’m very picky about who I choose to give my time to (as everyone should be).

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There’s nothing wrong with knowing what you want, people!

I’ve learned over time that if I plan a set of questions to ask, I can avoid potential deal-breakers that pop up down the road. Just like the filtering tool I use while online shopping, I use these questions to filter through what fits me and what doesn’t.

For example: if you don’t see yourself dating a cigarette smoker, wouldn’t you wanna ask that from the jump before you went on repeated dates with someone?

I also get so nervous on first-dates (which is surprising even for me because I’m such an outgoing person). Having questions ready has been an efficient way for me to get rid of some of those ‘first date butterflies’!

I do wanna point out that these are questions I’d ask someone I actually see myself being in a relationship with. These would be irrelevant for those who are going on dates solely to participate in today’s “hook-up” culture. (This is a non-judging zone by the way, this wasn’t a shot at those who are in that scene right now- do you boo!)

I’ve also included my boyfriend’s answers he gave on our first date just for kicks and so you can get to know us better hehe 😉

So without further ado,
Here are my 7 must-ask first date questions:


#1 – “Are you working on any personal projects right now/ Do you have a dream you’re pursuing/ Do you have a passion?”

These questions aim to find what they’re passionate about. Personally, I love when people speak about their passions- their eyes light up, it brightens the mood, and it’s a great icebreaker.

Deeper reasons you should ask:

If they have a passion, chances are they won’t complain about the long nights and the sacrifices you make for yours. They will not only understand your grind, but they’ll support it.

In contrast, I’ve dated someone who didn’t have a passion. They often complained about my commitment to mine and made me feel guilty for my dedication.

It’s important to date someone who lets you do what you love and lets you shine. Someone who will allow you to chase your dreams unapologetically.


My boyfriend’s answer on our first date

[Just as a side note: We talked for literal hours on our first date so these were his actual answers (but the condensed version of them!)]

“Football and saving the planet are my passions right now. I’ve been playing football since I was 4. As for environmental issues, when I moved to California I realized this state was way ahead of other states in terms of saving the planet. It became my passion to get the rest of the world on board.”


At the time I met him, he was an environmental engineering/sustainability major at Stanford focusing on water conservation and ending world hunger.

Present day, he’s still trying to conserve our planet, but redirected his efforts to renewable energy & reducing our carbon footprint.


#2 – “What was the last book you read?”


What people choose to read on their free time says a lot about who they are as a person.

There’s always something you can improve on in life, and those who read books normally have a strong desire for self-improvement.

It’s important to associate yourself with people you can learn from and who inspire you.

“A person who inspires you will never get boring. When we feel inspired, we feel alive. We feel elevated and excited. You will never completely figure out this person because he or she will always continue evolving/reinventing themselves.”
Paul Hudson


My boyfriend’s answer:

“Rich Dad Poor Dad by Robert Kiyosaki and Sharon Lechter


Rich Dad Poor Dad advocates the importance of financial literacy, financial independence and building wealth through investing in assets, real estate investing, starting and owning businesses, as well as increasing one’s financial intelligence. [Get the book here]

Fast-forward 3 years later into our relationship, I can confidently give my boyfriend credit for educating me on all those important topics.


#3 – “Who are the most important people in your life?”


It’s so beautiful listening to a person describe someone they love!

You can usually scope out a person’s character by paying close attention to how they talk about others. You can also assess his or her ability to form close relationships.


My boyfriend’s answer:

“My family is #1. My mom is the hardest working person I know, I owe my life to her. One day I’m gonna repay her for raising me to be the man I am today.”


I loved this answer because 1) it showed humility. He credited others for his successes in life 2) my mom is also the hardest working person I know. So we related to each other in that sense!


#4 – “What are your political views?”

Some people believe politics are a no-go on first dates because it can turn into a heated conversation (hence the tea photo I used lol).

But if you’re like me and date for a potential boyfriend (again, I don’t like to waste time), then I think it’s completely necessary to see if you and your date are compatible.

This can lead to seeing what kinda things they feel strongly about and if their moral compass aligns with yours (normally I don’t say this about politics, but with the politics we have nowadays it’s oh-so-necessary).

In addition to that, you get to see if your date can be respectful in exchanging different beliefs. A big turn off for me is when someone is unable to voice their opinion in a civil/mature manner.


My boyfriend’s answer:

Definitely aligned with mine! I won’t post any political views on here 😉


#5 – “How do you feel about the gender wage gap?”

I swear, every time I tell someone I legit ask this question on first-dates, they don’t believe me!

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Seriously, I am a feminist. I need a partner who’s just as big of a women’s rights advocate as me.

In the past, I’ve asked a date what he thought about the gender wage gap & he replied that he didn’t know what that term even meant.

Fast-forward a week after that date, he called me “stuck up” when I declined his offer to go back to his place after our second date (I honestly wish I was kidding!)

If you don’t believe in gender equality, then you don’t respect women. And if you don’t respect women guess what? You’re not gonna respect me, and you’re not gonna respect my boundaries.

PERIODDDDT.

That’s my belief. And I’m sticking to it.

“Feminism isn’t about making women stronger. We’re already strong. It’s about changing the way the world perceives that strength.” G.D. Anderson


My boyfriend’s answer:

I think the gender wage gap is ridiculous. And I think men need to do their part and speak up too. We need to back women on this fight for equality.”

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Present day (in our relationship), he admires the “strong” personality the men in my past disliked. He doesn’t let us conform to gender roles at the house, such as dishes and cooking (he actually cooks more than I do!), and he’s attended women empowerment events I’ve participated in.


#6 – Who is an inspiring public figure and why?

This can be both a fun question and a reflective one. Reflective because most of the time, the people you look up to you try to emulate.

For example, a public figure I am inspired by is Mother Teresa. She dedicated her entire life to help people, and is considered one of the 20th Century’s greatest humanitarian.

I aspire to be the incredible woman she was and try to incorporate her teachings into my everyday life.

My boyfriend’s answer:

Do Won Chang. Even after his multiple failed businesses he got up and kept it pushin! I admire his work ethic and drive.”


For those who aren’t familiar with his story, Do Won Chang worked as a janitor, gas station attendant, and in a coffee shop when he first moved to America. With no college experience, he and his wife built Forever21.

Today, the retailer brings in roughly $4.4 billion in sales from over 600 stores, and the Changs have an estimated net worth of $6.1 billion [Forbes].

A true rags to riches story.


Deeper into our first date, my boyfriend shared that he came from humble beginnings as well. He was actually the first person in his family to graduate college (on a full ride scholarship, mind you).

He is easily the hardest-working man I know.


#7 – “How long has it been since your last serious relationship?”

According to Gary Lewandowski, Ph.D. of Monmouth University, it’s normal to take several months to get over an ex. But, according to my own experiences– it takes longer than “several” months.

My rule of thumb is that a person would have to be single for full year for me to even take them seriously.

Again, this is a personal preference due to my own experiences on both ends of the spectrum- 1) I liked someone but they ended up going back to their ex and 2) I personally have gone back to my ex within that allotted time.

Of course, everyone heals at their own pace. But my has-been-hurt-too-many-times/overly-cautious self likes to play it safe in order to not be a rebound.

“Rebound relationships are a great way to boost someone’s ego while completely shattering an innocent persons life.”

-Author Steffi D’souza of NewLoveTimes warns those dating someone fresh out of a relationship.


My boyfriend’s answer:

“I’ve actually never been in a serious relationship before”


Okay there were two different ways I could interpret this information given to me:

  1. He is a serial dater, commitment-phobic, and has been too antsy to ever settle down
  2. His standards are ridiculously unreachable which leaves the possibility of extreme arrogance

So of course, I had to ask him why.

His response:

I’m super picky. Not in a ‘no one’s good enough for me’ type of way, but in a ‘I’m dating for possible marriage’ type of way. I think that too many men are either guilted into relationships they don’t want to commit to, but their women gave them an ultimatum.

Or, men just date to have company around cuz they can’t be alone. I like being alone. I don’t feel the need to have a woman around just to fill a void, I think that’s messed up and also a waste of time.

If I’m gonna commit to a serious relationship, it’s because I can see myself marrying you.”


(Me thinking to myself after that response):

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Conclusion

Those are my not-so-typical first date questions I asked my boyfriend. It was a great way for me to dig deep, and I’m glad I did because the way he treats me now (and has been treating me) is a reflection of those answers he gave me 3 years ago.

Of course, I’m not saying that if a person gave solid answers to these questions they’ll be the man/woman of your dreams. But these made it easier for me to weed out the dates that didn’t meet my standards.

Guys- you CAN have high standards without a high horse. It shouldn’t feel like a crime knowing yourself, knowing what you deserve, and then never settling for anything less.

Do not allow loneliness to lower your standards.
The people who are worthy of your time will rise up to meet them.


Thank you for reading!

If you enjoyed this read, I think you’d love my [Keep the Peace: The Best Advice I Have for Couples Living Together] post.


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