10 Creative Questions To Ask On A First Date

Cuffing season is back in full effect.


As cuffing season kicks off, many people are finalizing their rosters and securing their bae slots. If you're a little late to the party, cuffing season is the timeframe during the winter months where you're "off the market". During cuffing season, you could agree to be in an official relationship, or a situationship – it's completely based on your preference. The premise is simple though: it's cold outside, let's cuddle up!

Whether you're aiming to be "boo'd up" with your official bae or your cuffing season recruit, now is the time to get your date nights in before settling on your final pick. And if you typically struggle with date night questions, here are a few creative first date questions to get the conversation started!

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10 Creative First Date Questions

Is your work fulfilling? 

This is a creative spin to the "what do you do?" question. The answer to this question, if responded to elaborately, can tell you where they work, what they do, and what their professional passions are. It also has the potential to lend insight into their ambition and future professional plans, without having to ask the predictable "what's your five-year plan?" question.

What’s the last book you read? 

Typically, the books we read tell us about our interests or our fantasies. I'm either diving head first into self-help or inspirational books because that's what my spirit needs, or I'm drinking wine and reading a raunchy sex novel because celibacy is hard. Either way, what I read correlates directly to my interests – or my struggles. Allowing your date night partner to share more about what books are currently on their roster, can lead to a few good follow-up questions about what interested them to read the book, and what lessons they may have learned from it, bringing you a little deeper into their world. And if nothing else, it may give you an idea of the next book you should pick up.

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What are your thoughts on rape culture?

This is a question I know we all want to shy away from. The usual rule-of-thumb for first date questions is to avoid political conversations, but with the current start of our culture, this may be a very necessary question to ask. This can provoke a lot of interesting thought, or fuel an intense debate, however, it's not just about assessing political views as it is about personal safety. What someone feels about rape culture can highlight misogyny, sexism, and loads of other red flags. But, confrontational conversations don't have to be all bad, this question – if approached correctly – can serve as a great opportunity to educate each other.

Do you have a passport? 

Now I'm not saying that most people travel with their cuffing season boos, but I am saying, if you want to travel with your cuffing season boo, this question is imperative. You can't take an impromptu #baecation if bae isn't ready when it's time. There may be a valid reason why they don't have a passport, and that may be a conversation worth having. But if you're adamant about exploring different countries, be sure to find out if potential bae is too.

How do you define happiness? Would you say you’ve mastered it? 

So often in relationships we place the burden of our happiness on our partners. This question attempts to identify if this potential boo, falls into that same habit. Understanding someone's idea of happiness and if they've manifested it (or are at least trying to), can set the tone for the joy you may – or may not – experience with each other. It'll also give you an in to what brings them joy and if your idea of happiness aligns with theirs.

Who are you? 

There's nothing quite as fulfilling as dating someone who's self-aware. They know their quirks, their flaws, and everything in between. Someone who can define themselves within the context of their own self-discovery is well worth continuing to get to know. This question allows them to share with you, the person they've found in their own pursuit of discovery, and give them a moment of transparency for communicating to you exactly who they are.

Tip: don't have an expectation for their response. It's important that you allow your bae-candidate to authentically express themselves and whatever identities they uphold.

 What is important to you? 

Allow your date to open up and be candid about the important pieces of their life. I fell in love with my ex, in part, by how he spoke so lovingly about his son and how much having him changed his life. Allowing people the space to openly talk about the important parts of their lives helps shatter some walls and builds connection.

 Do you live alone? 

This isn't necessarily creative, but if you don't want to be snowed in with bae and two roommates, I suggest you get this question answered and out of the way.

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 When’s the last time you prayed? 

For me, spiritual connection is important. And while everyone is on their own journey – and at their own place of spiritual development – identifying the last time someone prayed is a huge marker to how frequently they commune with God; especially since someone's church attendance – identified by the usual "do you go to church" question – does not necessarily mean they have a relationship with God. This can also spark a conversation about faith, church, and other spiritual beliefs. Obviously, if faith isn't important to you, you can skip this one.

 Among your friends, what are you best known for? 

With this question, you'll learn more about the company bae keeps, and about what role they play in the clique. This can be important if you like to woo the crew, or if your single homegirls are still playing the field. Double dates "on fleek"! If you live in a small city, it'll also give you a moment to dissect their tribe and assess if that is the company you want yourself associated with.

It wouldn't behoove you to ask all these questions at once, as the date will quickly turn into a counseling session. However, asking a variety of these questions can offer insight into the person's heart and mind, and can provide the spark all first date conversations should be made of. Using these questions as a guide to incite thoughtful conversation and friendly debate (emphasis on friendly) can help weed out the f*ckboys and help ensure that your cuffing season bae is top quality.

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ACLU By ACLUSponsored

Over the past four years, we grew accustomed to a regular barrage of blatant, segregationist-style racism from the White House. Donald Trump tweeted that “the Squad," four Democratic Congresswomen who are Black, Latinx, and South Asian, should “go back" to the “corrupt" countries they came from; that same year, he called Elizabeth Warren “Pocahontas," mocking her belief that she might be descended from Native American ancestors.

But as outrageous as the racist comments Trump regularly spewed were, the racially unjust governmental actions his administration took and, in the case of COVID-19, didn't take, impacted millions more — especially Black and Brown people.

To begin to heal and move toward real racial justice, we must address not only the harms of the past four years, but also the harms tracing back to this country's origins. Racism has played an active role in the creation of our systems of education, health care, ownership, and employment, and virtually every other facet of life since this nation's founding.

Our history has shown us that it's not enough to take racist policies off the books if we are going to achieve true justice. Those past policies have structured our society and created deeply-rooted patterns and practices that can only be disrupted and reformed with new policies of similar strength and efficacy. In short, a systemic problem requires a systemic solution. To combat systemic racism, we must pursue systemic equality.

What is Systemic Racism?

A system is a collection of elements that are organized for a common purpose. Racism in America is a system that combines economic, political, and social components. That system specifically disempowers and disenfranchises Black people, while maintaining and expanding implicit and explicit advantages for white people, leading to better opportunities in jobs, education, and housing, and discrimination in the criminal legal system. For example, the country's voting systems empower white voters at the expense of voters of color, resulting in an unequal system of governance in which those communities have little voice and representation, even in policies that directly impact them.

Systemic Equality is a Systemic Solution

In the years ahead, the ACLU will pursue administrative and legislative campaigns targeting the Biden-Harris administration and Congress. We will leverage legal advocacy to dismantle systemic barriers, and will work with our affiliates to change policies nearer to the communities most harmed by these legacies. The goal is to build a nation where every person can achieve their highest potential, unhampered by structural and institutional racism.

To begin, in 2021, we believe the Biden administration and Congress should take the following crucial steps to advance systemic equality:

Voting Rights

The administration must issue an executive order creating a Justice Department lead staff position on voting rights violations in every U.S. Attorney office. We are seeing a flood of unlawful restrictions on voting across the country, and at every level of state and local government. This nationwide problem requires nationwide investigatory and enforcement resources. Even if it requires new training and approval protocols, a new voting rights enforcement program with the participation of all 93 U.S. Attorney offices is the best way to help ensure nationwide enforcement of voting rights laws.

These assistant U.S. attorneys should begin by ensuring that every American in the custody of the Bureau of Prisons who is eligible to vote can vote, and monitor the Census and redistricting process to fight the dilution of voting power in communities of color.

We are also calling on Congress to pass the John Lewis Voting Rights Advancement Act to finally create a fair and equal national voting system, the cause for which John Lewis devoted his life.

Student Debt

Black borrowers pay more than other students for the same degrees, and graduate with an average of $7,400 more in debt than their white peers. In the years following graduation, the debt gap more than triples. Nearly half of Black borrowers will default within 12 years. In other words, for Black Americans, the American dream costs more. Last week, Majority Leader Chuck Schumer and Sen. Elizabeth Warren, along with House Reps. Ayanna Pressley, Maxine Waters, and others, called on President Biden to cancel up to $50,000 in federal student loan debt per borrower.

We couldn't agree more. By forgiving $50,000 of student debt, President Biden can unleash pent up economic potential in Black communities, while relieving them of a burden that forestalls so many hopes and dreams. Black women in particular will benefit from this executive action, as they are proportionately the most indebted group of all Americans.

Postal Banking

In both low and high income majority-Black communities, traditional bank branches are 50 percent more likely to close than in white communities. The result is that nearly 50 percent of Black Americans are unbanked or underbanked, and many pay more than $2,000 in fees associated with subprime financial institutions. Over their lifetime, those fees can add up to as much as two years of annual income for the average Black family.

The U.S. Postal Service can and should meet this crisis by providing competitive, low-cost financial services to help advance economic equality. We call on President Biden to appoint new members to the Postal Board of Governors so that the Post Office can do the work of providing essential services to every American.

Fair Housing

Across the country, millions of people are living in communities of concentrated poverty, including 26 percent of all Black children. The Biden administration should again implement the 2015 Affirmatively Furthering Fair Housing rule, which required localities that receive federal funds for housing to investigate and address barriers to fair housing and patterns or practices that promote bias. In 1980, the average Black person lived in a neighborhood that was 62 percent Black and 31 percent white. By 2010, the average Black person's neighborhood was 48 percent Black and 34 percent white. Reinstating the Obama-era Fair Housing Rule will combat this ongoing segregation and set us on a path to true integration.

Congress should also pass the American Housing and Economic Mobility Act, or a similar measure, to finally redress the legacy of redlining and break down the walls of segregation once and for all.

Broadband Access

To realize broadband's potential to benefit our democracy and connect us to one another, all people in the United States must have equal access and broadband must be made affordable for the most vulnerable. Yet today, 15 percent of American households with school-age children do not have subscriptions to any form of broadband, including one-quarter of Black households (an additional 23 percent of African Americans are “smartphone-only" internet users, meaning they lack traditional home broadband service but do own a smartphone, which is insufficient to attend class, do homework, or apply for a job). The Biden administration, Federal Communications Commission, and Congress must develop and implement plans to increase funding for broadband to expand universal access.

Enhanced, Refundable Child Tax Credits

The United States faces a crisis of child poverty. Seventeen percent of all American children are impoverished — a rate higher than not just peer nations like Canada and the U.K., but Mexico and Russia as well. Currently, more than 50 percent of Black and Latinx children in the U.S. do not qualify for the full benefit, compared to 23 percent of white children, and nearly one in five Black children do not receive any credit at all.

To combat this crisis, President Biden and Congress should enhance the child tax credit and make it fully refundable. If we enhance the child tax credit, we can cut child poverty by 40 percent and instantly lift over 50 percent of Black children out of poverty.


We cannot repair harms that we have not fully diagnosed. We must commit to a thorough examination of the impact of the legacy of chattel slavery on racial inequality today. In 2021, Congress must pass H.R. 40, which would establish a commission to study reparations and make recommendations for Black Americans.

The Long View

For the past century, the ACLU has fought for racial justice in legislatures and in courts, including through several landmark Supreme Court cases. While the court has not always ruled in favor of racial justice, incremental wins throughout history have helped to chip away at different forms of racism such as school segregation ( Brown v. Board), racial bias in the criminal legal system (Powell v. Alabama, i.e. the Scottsboro Boys), and marriage inequality (Loving v. Virginia). While these landmark victories initiated necessary reforms, they were only a starting point.

Systemic racism continues to pervade the lives of Black people through voter suppression, lack of financial services, housing discrimination, and other areas. More than anything, doing this work has taught the ACLU that we must fight on every front in order to overcome our country's legacies of racism. That is what our Systemic Equality agenda is all about.

In the weeks ahead, we will both expand on our views of why these campaigns are crucial to systemic equality and signal the path this country must take. We will also dive into our work to build organizing, advocacy, and legal power in the South — a region with a unique history of racial oppression and violence alongside a rich history of antiracist organizing and advocacy. We are committed to four principles throughout this campaign: reconciliation, access, prosperity, and empowerment. We hope that our actions can meet our ambition to, as Dr. King said, lead this nation to live out the true meaning of its creed.

What you can do:
Take the pledge: Systemic Equality Agenda
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