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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