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So, you’ve finally agreed to go on that blind date your best friend has been dying to set up. Everything is planned: the fun activity, the romantic restaurant, the cute outfit…but your nerves are wreaking havoc, and you’re suddenly flooded with memories of past first-date disasters.
The uncomfortable questions, the awkward silences, the panic rambling, the “get me the hell outta here” feeling…
Listen, I know how nerve-wracking it can be – I’ve been there.
Not knowing what to say, what to ask, or asking the
wrong questions can blow any chance of a second date.
But, let’s take a second and try not to overcomplicate it. First dates are meant to be
fun. They are an opportunity for first impressions, to gauge whether the person sitting across from you could have a place in your life.
To help decrease the pressure and lean into the pleasure of dating, I’ve created a list of perfect ice breaker questions as well as questions to avoid – aka
deal breakers. These will help navigate conversations – especially when things get quiet – and bring out the best in your dating experience(s).
First Date Ice Breakers
These questions are sure to spark fascinating conversations, and, at worst, they’ll reveal incompatible characteristics.
These questions are easygoing, yet capable of highlighting shared interests and values. Of course, I am not suggesting to
never explore the deep and challenging stuff. Avoiding those questions altogether is not practical for long-term relationships; however, there is a time and a place for certain interrogative or personal questions – like when you and this person have built a foundational (and mutual) level of trust and comfort.
Until then, here are questions that are sure to spark fascinating conversations and lead you to interesting discoveries about your date.
What do you enjoy doing in your free time?
Knowing what a person enjoys doing in their free time will expose you to their interests and priorities in life.
Who in your life do you admire most or feel most grateful for, and why?
Having an idea of what your date values in other people can reveal a lot about their character and relationships. It also reveals the most important people in their life.
What are some random fun facts about you?
Explore what your date finds interesting about themselves, and see if they are qualities you enjoy in a person.
Do you have any particular projects that you’re working on?
Is your date creative, hands-on, ambitious, or curious…? What do their passion projects say about them?
What aspect of dating do you dislike most?
Connect on the awkwardness of dating by calling out the difficult bits. Laugh at past mishaps and cheers to making the best of the current situation.
Do you have any children?
Whether you see kids in your future or not, get this one out of the way. The sooner this information is revealed, the more informed your decision will be to carry on dating.
Do you have any pets? Why or why not?
Do you both have a shared love or dislike for fur babies? Is your date a cat lover or dog lover?
What does a typical day in your life look like?
Take a peek inside their private world. Do you see how you could potentially fit in? Does their routine feel compatible with your own?
Do you prefer the indoors or the outdoors?
If they could pick, would they go hiking or Netflix-and-chill? If you have a specific love for one or the other, it may be worth finding out their preference.
What is something that people are always surprised to learn about you?
Can they speak another language? Are they passionate about a specific cause? Do they have a famous relative? This may have some fun reveals.
What do you love most about your job/career?
Digging into the “why” behind your date’s career choices can reveal their level of ambition, self-efficacy, passion, and values.
What were you like as a child? As a teenager?
Were they a menace? Class clown? Tap into their child-self and see what comes out.
What is your favorite food?
Just giving you ideas for date number two!
What is the best gift you’ve ever received?
Is it something sentimental? Or a possession they’ve always dreamed of having?
What is the best gift you’ve ever given?
Find out what kind of gift-giver they are and how well they know their recipients.
What is your favorite game or sport to watch and play?
…Date number three? A chance to explore their competitive side?
Where do you see yourself in five years?
Get a glimpse of their desired life course. Does it appeal to you?
How would your friends describe you?
Friendships matter! Find out what role they play in the lives of their pals.
What’s on your bucket list this year?
Are they goal-setters or globe trotters? What exactly do they want to accomplish this year?
What is a relationship deal-breaker for you?
Knowing the non-negotiables can save a lot of time and heartbreak!
What would be your ideal destination for a vacation?
Discover their vacay avatar – is it similar to yours?
What do you wish you had more time for?
Find out the non-priority priority – what in their life didn’t make the cut?
First Date Deal Breakers
The reason certain questions are categorized as
deal breakers rather than ice breakers is that they may be considered intense, intrusive or demeaning for first dates (or ever). When you’re asking your date questions, remember that they do not know you or your intentions, and a lot can get lost in translation.
Additionally, you don’t yet know their comfort level on specific topics, such as sexuality, family history, or health. These topics require
trust to access. Asking deal breaker questions apropos to nothing can give a negative impression of your character, potentially squandering chances for a second date.
In saying that, if difficult topics do arise naturally, don’t avoid them. If you aren’t ready to speak about them, let your date know. On the flip side, reassure them that they also shouldn’t feel pressured to reveal certain personal subject matter at this stage.
As mentioned, the deep and challenging stuff is critical for long-term sustainment; however, the purpose of a first date is to get a general feeling for a person. If you want to get the most out of your first date experience, avoid these questions…
❤️ Do you have any mental illnesses?
❤️ Why did your previous relationship end?
❤️ Why are you still single?
❤️ Do you see marriage in
your near future?
❤️ How many people have you slept with?
❤️ How much money do you make?
❤️ What part of your body is fake or augmented?
❤️ Where do you see
this relationship going?
❤️ Do you want kids?
❤️ Have you been unfaithful in past relationships?
❤️ How much do you weigh?
❤️ Do you have hot friends?
❤️ Do you love me?
❤️ Are you going to break my heart?
❤️ Do you want to know about my ex?
❤️ Are you seeing anyone else?
❤️ When was the last time you had sex?
Ice Breakers Versus Deal Breakers
Sticking to the icebreaker questions will keep the conversations safe and interesting. They are open-ended on purpose to help move you and your date to more in-depth, personal discoveries that do not risk offense, and may lead to trust building.
Ideally, first dates should be fun and low-pressure. If the difficult stuff arises, trust your instincts! Let your date know when you aren’t comfortable disclosing certain details this early on.
If you allow it, dating can be one of the greatest phases of your life. It reveals what you need in a partner, what you don’t want, and where you need to grow to be the best version of yourself for your future relationships.