The Deep End: 10 Questions To Create Depth In Conversations

Earlier this week we wrote a piece for our readers who are either online dating during the pandemic, or wondering why dating feels more anxiety-inducing than ever.

We suggested that one of the keys to maintaining momentum with online dating (especially during a lockdown) is to create depth in conversations.

Even if you are not dating, we can all relate to feeling starved for connection these days!  Since we are not seeing other people and perhaps even calling or texting them less often (raise your hand if you like to cocoon and hibernate for winter 🐻 ) the quality of our interactions matters more than ever.

Is Depth Just One More Thing I Have To Think About Now?

Meeting new people, pandemic or not, can be awkward and nerve-wracking. We feel vulnerable and self-conscious, unsure of ourselves and eager to make a good impression. Often, we are so preoccupied with whether our date or companion likes us, that we pay little attention to whether we even like THEM.

So you might be wondering, Sarah do you seriously expect me to deal with all that and also worry about being deep and intellectual? 🧐🧐🧐

Well, the key is to increase depth, not pretend to be someone you are not! Conversations that are deep do not have to be intellectual or 'high brow'. In fact, those types of conversations can be another way to keep things at a surface level. Don't want to get deep? Debate a topic till it's dead.

Conversations at a surface level are actually harder to maintain because the topic inevitably fizzles out. When you get deeper, the conversation is less nerve-wracking because the source material is YOU. And we usually don't run out of things to say about ourselves.

So how do we move past the small talk and pleasantries and wade into the deep end?

Be Willing To Make The First Move

We are naturally more likely to be vulnerable and open with people who are vulnerable and open with us! That's right, sometimes you have to share first to get the ball rolling.

When you share something vulnerable, you are helping foster emotional intimacy. And it doesn't necessarily have to be something that is embarrassing or too personal! Always prioritize your safety when sharing information about yourself. Laying out your deepest traumas is not the pinnacle of vulnerability. In fact, it can be an overwhelming or even confusing experience when we talk about trauma without establishing trust and safety first!

So we don't have to bare all our wounds. If we want to get closer to people though, we do have to take some emotional risks. Especially if we meet someone on a dating app and really hit it off with them. With our current lockdown restrictions in Ontario, things can fizzle out pretty quickly, even if they are looking promising.

Try opening the conversation by talking about something that is important to you. Anchor it around yourself. For example, you can talk about your values or the kind of household that you grew up in. Or perhaps share some memories or worries of the past year.

Reward Vulnerability

This is so important! No one will wade into the deep end with you if they believe you might judge them, or think of less of them. When someone shares something that is personal or puts them in a vulnerable position, we can follow this up with words of support, reassurance, and encouragement.

How do we reward vulnerability with words? Here are a few examples.

"Thank you for sharing that with me"

"I feel honoured that you shared that with me"

"I feel closer to you now" or "I feel like I know you better now"

"It's so cool that we can talk openly about this stuff"

"I'm going to keep what you said in confidence, don't worry"

10 Questions To Get You In The Deep End

An important part of creating depth in conversations is asking thoughtful, intentional questions. Careful not to make it sound like an interrogation though! Balance is key here.

Keeping it heavy all the time is not the best way to get to know someone. Neither is the reverse, when we try to keep things constantly light. Although, sometimes lightness is what you need, and that's alright.

If, however, you want to get to know someone on a deeper level, try sprinkling in these thoughtful questions and see what happens.

You'll notice that these questions are all SIMPLE and most importantly, OPEN-ENDED. Don't get bogged down in trying to be creative of insightful. Ask about what interests you and what would help you feel closer to someone.

I mentioned a few of these in my recent IG post on 5 deep first date questions👇🏽👇🏽👇🏽

Here we go!

1. Can You Remember The Last Time You Cried And Why?

Even if the answer is a book or movie! For many of us, crying is a very private thing. If asking someone about the last time they cried seems a bit too personal, try asking what makes them cry in general.

2. What Do You Feel Is Your Greatest Accomplishment To Date?

We light up when we talk about things we are proud of. This is a great way to see what people value and also their ability to give themselves credit where credit is due!

3. How Do You Want To Be Loved And What Does Love Mean To You?

We all want to be loved in different ways. Additionally, we may give and receive love differently. This is a great question to ask someone you are really interested in.

4. What Things Or Situations Make You Feel Unsure About Yourself?

We are not perfect. Most of us carry a catalog of insecurities. It takes a fair bit of vulnerability to admit what makes us feel self-conscious or insecure.

5. When Was The Last Time You Said 'I Love You' To Someone?

The answer may surprise you! Like we mentioned above, we all express love differently. It's always worthwhile to learn about how people let their loved ones know how valuable they are to them.

6. What Is Your Favourite Place In The Whole World?

This might be a nice way to dream a little together (especially in a pandemic). Their favourite place might even be a local spot, and that can become the site of a future in-person date!

7. What Is Something You Want To Learn More About And Why?

Because there is wisdom and humility in knowing what you don't know.

8. Do You Feel That You Are Living Your Values?

Values can be a make-or-break topic for many budding relationships.

Having a strong foundation of common values is important for many couples. Sometimes there can be discrepancy between our values and actions, because living our values is often challenging. Asking about these challenges is a nice, non-judgemental way to explore the values conversation.

9.  What Are You Most Known For Amongst Your Group Of Friends?

This question can tell you a little more about their personality.

10. Who Are The People You Respect And Admire The Most In Your Life And Why?

We often emulate who we respect and admire! It's always valuable to know who a potential partner considers a mentor or someone worth admiring.

Wrapping Up

Wading into deep waters with people can be tough, especially if we don't know them too well. In general, getting to know people is challenging because we put pressure on ourselves to make sure the experience is worth our time. This is what gets in the way of us being in the moment!

Disrupt this process by asking thoughtful, intentional questions and reflect on how you feel when your date or companion answers them. Sometimes, these questions can help us get deep with ourselves too! Flip the script and try answering them. You may find that they whole process helps you get to know yourself better too.

Until next time!

Sarah Ahmed


WellNest Psychotherapy Services

Sarah Ahmed is the co-founder and a psychotherapist at WellNest Psychotherapy Services. Sarah strongly favors an integrative, trauma-informed, client-centered approach to create a healthy alliance with clients and their loved ones.