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ADVICE HOME RELATIONSHIPS AND RELATIONS

25 Questions To Help You

Get To Know Someone
Deeply
Updated May 9, 2023 by BetterHelp
BetterHelp Editorial Team
Medically reviewed by April
April Justice, LICSW

Humans are a naturally social species. Even the most

introverted individuals may find themselves looking
for deep, meaningful connection with other people –
whether that’s romantic, platonic, familial, or any
other relationship.

Often, though, people find themselves feeling

nervous or overwhelmed by the idea of idle chat and
small talk. So, how do you break down the barrier of
awkwardness that can come with new
introductions?

Learn How To Better Understand

People From A Licensed Counselor

Connect With A Professional Counselor

It can be as simple as asking the right questions

questions to
get to know someone
someone. Open-ended questions
can get to the heart of someone's values,
personality, and beliefs of the world without feeling
intrusive or trespassing on their privacy.

Questions Can Make Conversations More

Interesting

Asking "getting-to-know-someone
getting-to-know-someone
questions
questions" can enable you to learn more about
their life and the potential for your relationship.
Funny questions can help lighten the mood, and
icebreaker questions may reduce nervousness
or tension.

Questions can help you get to know each other, and

become comfortable in each other’s company. When
the person you’re with answers with enthusiasm and
openness, the conversation might lead to deeper
and more personal topics.

Remember, though, that everyone has the right to

refuse to answer questions that feel too personal or
invasive, and shouldn’t be pushed to give an answer
they’re uncomfortable with. It’s important to be
respectful of other people’s privacy and comfort
level when it comes to conversation, and to abide by
the boundaries they put in place.

25 Questions To Help You Get To

Know Someone Deeply

Whether you're trying to strengthen a friendship that

you've had for years or become more intimate with
your significant other, well-chosen questions can
spark a conversation that can help you get to know
them in ways you never have before.

Here are 25 questions that you can ask to engage

others in meaningful conversation.

What Achievement Are You Proudest Of?

Asking about what someone is proud of can reveal

a lot about their personal values
values. Some people
might consider their job performance to be their
biggest achievement. Others might put more value
on relationships with friends and family. Others may
hope for certain achievements in the future. 

How Did You React To Your Biggest Mistake?

Taking an honest look at past mistakes, as well as

the sincerity of your efforts to improve yourself, can
help you learn more about yourself as a person.
Asking this allows you both to explore how the
responding party is trying to better themselves.

If You Could Go Back And Change One Decision In

Your Life, What Would It Be?

Though similar in theme to the previous question,

this focuses less on mistakes and more on past life
events. The answer may tell you how this person has
changed over time, and how their values and beliefs
have shifted.

What Is Your Biggest Dream In Life?

Where does this person want to go in life? They may

respond with dreams for their career, their living
situation, or their future relationship goals such as
marriage or parenthood. Asking about future
aspirations can help you decide whether or not you
can visualize yourself as a part of another person’s
life in the long term.

What Was Your Childhood Like?

A person's childhood can give you a lot of

information about who they are
are, as can their
feelings about that childhood. Maybe they have a lot
of happy memories from when they were a kid, such
as birthdays or sports, but they have not had the
chance to open up about how they were
raised. Conversely, they may have had unpleasant
experiences and wish to do better for themselves
and their loved ones as an adult.

What's One Thing That You Wish People

Understood About You?

Sometimes, appearances are deceiving, especially

with the rise of social media. Some people may feel
that they need to conform to a certain standard for
their public image to remain intact, while others may
feel misrepresented by the public perception
associated with them. This question may allow you
to see what someone values about themselves that
others may not see. 

What Is Something You Are Working To

Improve In Yourself?

Though it can be uncomfortable to consider,

understanding the things that we consider to be
areas of improvement in our lives can greatly
improve how we interact. Discussing the negative
aspects of your personalities can help both parties
of a relationship to better understand each other and
how you fit (or don’t fit) into each other’s lives.

What Event In Your Life Has Shaped You Most

As A Person? How Did It Do So?

Asking about important moments in life can offer you

valuable insight into a person's past. This defining
moment in their mind may help inform your opinion
about many decisions and behaviors as the
friendship progresses that would otherwise be
mysterious.

Have You Ever Treated A Person In A Way That You

Regret?

The answer can reveal much about what someone

considers to be the right and wrong ways of treating
others. It can also tell you more about how you might
expect to be treated in the course of the friendship.

Do You Think It's Possible To Be "Just Friends”

With Someone Of Another Gender?

It is important to define the nature of a relationship

and the expectations you have for each other from
the outset, especially in the often socially
questioned scenario of a cross-gender friendship.
Though it is perfectly possible for people of all
genders to be friends, some people have had
unhealthy exposure to flawed expectations about
romantic interaction. If this is the case, knowing from
the outset can help you set healthy boundaries in
the relationship.

Would You Rather Be Rich And Lonely Or

Financially Destitute With Lots Of Great
Family And Friends? Why?

This is another question which may speak volumes

about a person's priorities. Some people may place
more value on personal stability while others may
focus more fully on rich, interpersonal lives. Knowing
which your responder prioritizes can help you
understand their boundaries in the relationship.

What Role Does Alcohol Play In Your Life?

Being under the influence of a substance often leads

to the loss of a person’s usual inhibitions and “filters,"
meaning that they are more likely to speak and act
without considering the consequences.
Understanding how a person acts when intoxicated
(and how often they are in that state) can help you
determine boundaries when it comes to behavior
and the use of substances.

If You Could Change One Thing About

Yourself, What Would It Be And Why?

Once again, this is a question that examines what

someone values, what they may perceive as a flaw
in themselves, and what they might be doing to
improve themselves. It can also offer you a way to
understand what topics you should be sensitive to
when talking to and about this person.

If You Knew You Would Die Tomorrow, How

Would You Spend Today?

Considering your mortality often prompts you to

confront the things that you most value but might
not consider to be immediate priorities, because you
may assume you have plenty of time to address
them later on.

What Does Happiness Mean To You?

Happiness is subjective, so the answer to this

question can show you what your responder
considers happiness to mean, and what makes them
happy, both in the short term and the long term. It
can help you see what allows them to feel content
and what excites them.

Have You Ever Been In Love?

Everyone’s experience with love is different. While

some people may consider romantic love to be vital
and pivotal in their lives, others may more greatly
value having fallen in love with a hobby, career, or
group of devoted friends. All healthy forms of love
are valid, and they can give you insights into a
person’s life.

When You're Home Alone, And Nobody Else Is

Around, How Do You Like To Spend Your
Time?

A person may be most relaxed when they don’t feel

that they are being observed, so understanding how
your responder acts when they are alone can help
you to see what makes them feel content, safe, and
fulfilled.

What Do You Want People To Say In Your Eulogy?

This can show you what a person wants to

accomplish in their life, as well as the kind of
impression they hope to make on others.

If You Could Have A Conversation Over Coffee

Or Food With Anyone Living Or Dead, Who
Would It Be And Why?

Whatever the response is for this question, you can

discover the kind of person your responder admires
the most, revealing attributes that they value above
all. This can be an effective way to find out more
about their interests as well. You might even take the
question a step further and ask who they would like
to be trapped on a deserted island with to find out
who they would want to be around when it matters
most. 

Do You Think You're A Genuinely Good

Person?

This question is helpful in sorting out your friend's

standards of worth and what it means to be a “good”
person at all.

How and Why Did You Choose Your Current

Profession?

Asking this question can help you understand

whether this person is content with their path in life.
Are they making steady progress towards their
goals, or ready to mix things up at any given
moment?

If Money Were Not An Issue, How Would You Spend

Your Time Each Day?

The business of earning a living often gets in the

way of personal ambitions. Learning about the
hopes and dreams your friend may hide underneath
the routine of daily life can reveal a lot about their
interests and personality. 

How Do You Lean Politically?

A reasoned, calm discussion of opinions and

personal views may help you and your responder
understand each other’s worldview, which can point
you toward core values you both hold for quality of
life and the equity of people across cultures.

What's One Thing That You Do On A Regular

Basis That Nobody Knows You Hate Doing?

This is a unique way to discover someone's likes and

dislikes, as well as how much they are willing to give
up for others’ needs or for a cause they deem
necessary.

Takeaway

If you have trouble making social connections or

developing meaningful friendships—or if you
have a significant other and want to deepen
your emotional connection—consider using a
professional counseling service. Online
counseling can be an excellent way to work on
your social skills. Research shows it can be
effective at improving communication in
relationships as well as personal confidence in
social interaction.

Through online therapy with BetterHelp, you

can be matched with a counselor whom you can
speak with from your own home. You may also
message your counselor at any time with
questions, which can be convenient if you find
yourself wanting to review certain interactions,
or better understand social cues you encounter
in your daily life.

Read More

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The information on this page is not intended to be

a substitution for diagnosis, treatment, or
informed professional advice. You should not take
any action or avoid taking any action without
consulting with a qualified mental health
professional. For more information, please read
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