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What Dating Can Teach You About Yourself

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By Natasha Ivanovic


Someone asked you out on a first date, and you said yes. Great! Perhaps this person will end up being your partner and if not, that’s cool too! What’s important is that you’re putting yourself out there, creating opportunities for connection, and learning as much as possible—about yourself and others.

While we know that first dates are a generally unavoidable step in finding a partner, they can also be one of the most dreaded. Why? Because there’s an immense amount of pressure surrounding first dates. You’re likely meeting someone you don’t know and you’re not only supposed to learn everything about them but identify any red flags and be completely charming all at once. 

Here’s the thing: going on a first date doesn’t have to be an anxiety-ridden event. If re-framed, it can be a time for enlightening self-discovery as well as personal growth—and hopefully you’ll have some fun in the process, too! 

This toolkit is intended to prepare you for the dating world by demonstrating the importance of knowing yourself before dating. Typically, priming yourself for dating is limited to how to attract the other person, but that mindset rarely touches upon your own wants and needs from a romantic relationship. 

So, whether you’re going back to dating after a breakup or dipping your toes into the dating world for the first time, we’re going to walk you through the process of self-reflection and raise some thought-provoking questions to ask yourself before dating, BBXX style 🙂

After reading this toolkit, our hope is that you’ll have a better perspective on yourself, what you want and who you want to become—and how these components all apply to the dating world. 


The Importance of Knowing Yourself Before Dating

You may have heard people tell you, “If you really want to love someone, love yourself first.” When you’ve been single for a while and have gone on a couple of nightmare dates, that might be the last thing you want to hear. You’re over the clichés and words of wisdom. And you know what? We’ve all been there. But here’s some questions to mull over: 

What are the reasons you are seeking a relationship? 

What type of relationship are you seeking (casual, or serious)? 

What type of partner are you looking for? 

Societal pressure tends to heavily focus on finding a partner, settling down, and having children. We have been spoonfed this life path from childhood and, while that doesn’t necessarily mean it’s a bad path to take for yourself, if that is our goal, it is important to understand the motivation behind it. Otherwise, if we simply abide by societal pressure,  we will consequently  overlook the most important relationship of them all—the one with ourselves.

“Your relationship with yourself is arguably the most important relationship in life,” says Dr. Grand Hillary Brenner in his piece on self-relationships in Psychology Today. He’s right. Being happy with yourself before dating is crucial in forming a healthy and loving relationship with another person. You set your own standard when it comes to love and the relationship you see yourself being in and that is why being single can be such an important phase in life. During this time, we have the opportunity  to invest in getting to know ourselves, learning what we like and dislike, form your own opinions and hone in on your values, and cultivate a strong sense of self-worth. 

By recognizing your unique qualities and attributes, you learn to appreciate yourself outside of a relationship. You understand that a relationship isn’t something that should make you feel whole, rather, it’s a conscious choice to share your experiences with another person and grow within your partnership. When you develop self-worth and self-love, instead of entering the dating world with the need to find someone, you will be looking for a person with whom to share with and complement your life.


Reading & Resources for Self-Discovery

To get to know yourself on a deep level, it requires some deep work. However, we’ve done some of the heavy lifting for you and we’ve put together some key resources to guide you on your self-discovery journey.

The following resources will give you a foundation for learning how to self-reflect and explore some of life’s most important questions. In doing so, you’ll not only achieve a better understanding of yourself but of your needs and desires within a romantic relationship. 


Many of us have had our share of unhealthy or even toxic past relationships. And while we’d all like all to improve the quality of our relationships (present and future), we often forget that we hold the power to do so in our own hands. WeDeepen focuses on human interaction and connection, helping people to develop healthy relationships through their online community. 

The BBXX Podcast – Mike Sagun 

We had the pleasure of speaking with personal development and men’s coach Mike Sagun regarding the art of self-discovery. During our conversation, Mike shared his journey through life and the tools he used for exploring his own identity. 

Not Yet Married: The Pursuit of Joy in Singleness and Dating

Many of us grew up with the understanding that meeting someone and getting married would solve all our problems. But life isn’t just about finding love. The novel Not Yet Married: The Pursuit of Joy in Singleness and Dating by Marshall Segal, looks at singleness from a spiritual point of view and speaks to the importance of living in the present rather than constantly fixating on the future.


It’s easy for us to equate our own happiness with being in a romantic relationship. But what really makes us happy? The Academy Award-nominated director Roko Belic decided to answer that question in his film, Happy. Belic takes us on a journey around the world, searching for the answer to what true happiness is. Spoiler alert: it’s not money or possessions! 

Scientific American: 10 Things You Don’t Know About Yourself

Modern day lifestyles don’t allow much time for inward reflection. Though no one likes to admit it, there are a few things you probably don’t know about yourself, and it’s time to take a deeper dive into what makes you, you. This article talks about how our brains can often deceive us from learning about who we really are.


Reading & Resources for Dating Preparation

After going through the resources above, you might realize that you don’t know as much about yourself as you had originally thought. As it turns out, that’s a great spot to be in. As Socrates says, “The only true wisdom is in knowing you know nothing” and, as Aristotle says, “Knowing yourself is the beginning of all wisdom.” So, now that you’re aware, you can start working on life’s most important work—getting to know yourself. 

If you feel you’re ready to date, it’s always beneficial to ask yourself questions about your needs and desires beforehand. 

When you don’t know what your needs are, it’s very easy for someone else to make those personal decisions for you—jeopardizing a healthy foundation for the relationship. Here are some resources that will help you understand what you’re looking for (casual, serious, monogamous, etc.) and to help inform and define intentions for your future dating experiences. 

The BBXX Podcast – Casual Conversations: The Paradox of Perfection

With the rise of social media, beauty filters, and dating apps, it’s not hard to believe we’re living in a world struggling with perfectionism. But there’s so much more to perfectionism than you might think! On this episode of the BBXX podcast’s Casual Conversations series, Vitale Buford speaks to the deeper issues behind perfectionism and the danger of living to please others. Naturally, this heavily ties into your relationship with yourself, dating experiences, and how you go about choosing the the person you choose to be with.

Rewriting the Rules: An Intergrative Guide to Love, Sex and Relationships

Whether you haven’t dated in a while or are looking for your first relationship, we highly recommend Meg Barker’s novel, Rewriting the Rules: An Integrative Guide to Love, Sex and Relationships. The dating world, though on the surface may appear straightforward, is rather complex. There are many unspoken rules, but this book talks about rewriting those rules and choosing an approach that best suits your life. 

Self-Esteem vs. Self-Worth: Dr. Christina Hibbert

We often hear people talking about the notion of ‘low’ self-esteem, but what does that really mean? Dr. Christina Hibbert answers a Q&A on self-esteem, talking about the differences between self-esteem and self-worth and why we should be focusing more on the latter.

The Art of Manliness, Ep. 584: How to Avoid Falling in Love With the Wrong Person

After a bad date or a toxic relationship, we often ask ourselves, why do we fall in love with the wrong people? This Art of Manliness podcast features John Van, therapist and author of How to Avoid Falling in Love with a Jerk. Van discusses societal ideals of the perfect relationship, why people miss the signs of a jerk, and what you need to know about a person before starting a relationship with them. 


Reading & Resources for Dating

After going through your journey of self-discovery, perhaps you’ve decided you’re ready to date. You went through the process and you feel ready to enter the dating world with an open heart, focused on your intentions for the process rather than your expectations for the outcome. You understand that you’re not dating to find someone who will complete you but who will complement you as you learn and grow together. As your own person, you are already whole. You choose to be with someone you can share your experiences with, rather than being with someone to fill a void.

If you’re going on a first date, you want to be prepared. The below resources provide some insight on questions you should ask your date, as well as answers to big questions—from goals and money to sex and intimacy. 

Eight Dates: Essential Conversations for a Lifetime of Love

Who knows what is going to come from this date; maybe you’ll end up seeing them a couple of times and nothing progresses beyond that, or maybe this person will become your life partner. But during those first few dates, it’s not a bad idea to ask your partner some of the questions from the book, Eight Dates: Essential Conversations for a Lifetime of Love by John Gottman. This book pushes you to talk about the eight subjects—money, sex, trust, conflict, family, adventure, spirituality, and dreams—that will help you better understand each other.

Swipe Life: 12 Radically Honest Questions to Ask Your Dates

Your dates shouldn’t feel like an interview, but at the same time, there are some questions you’ll want to ask to gauge where the other person is at with respect to future goals and values. This article highlights 12 essential questions to ask your date.

The BBXX Podcast – Casual Conversations: Anxiety, Boundaries, and Meditation

Dating, whether you’ve been on twenty first dates or one, can make us feel anxious and stressed. So, how do you combat those feelings? On the BBXX podcast, we spoke to anxiety coach Amanda Huggins about the unique distinction of joy versus happiness and the importance of setting boundaries. 

200 (Not Boring) Questions To Ask To Get To Know Someone Better

The one thing people fear when on a first date is the conversation itself. No one wants to sit in silence with their date. What do you talk about when you don’t know the person? Well, here are 200–yes, 200–questions that you can ask your date to help you get to know them. We don’t recommend a rapid-fire, 200-question-on-one date approach, but picking and choosing a few that resonate with you most is a great place to start. 


Tying it all together

When it comes to dating, particularly online dating, it can be all too easy to focus  on the other person and what they want, the influence of societal standards, or surface level characteristics. Not only will that lead to relationships built on a shaky foundation (at best), but it is likely to be at the cost of  our own needs and desires. However, by bringing your awareness to the above tools and resources, you can take control of your dating life and focus on the things that matter on a deeper level—making decisions based on what you want, rather than what your date is looking for or what society is telling you to do.

Self work is hard work but it’s also the most important work that builds the foundation for any relationship.  You can only go as deep with others as we can go with ourselves. Thus, the deeper you connect with yourself, the deeper you will be able to connect with others. We hope that this toolkit helps you explore self-understanding and give you insight as to what your key ingredients are for creating a healthy relationship—be with yourself or someone else. 

Whether you’re dating for the first time, returning to it after some time of, or well-practiced in playing the field,, we invite you to embark on your journey to self-discovery and to equip yourself with the knowledge and the tools necessary to set yourself up for success. Once you have the answers (or at least some of them) to some of the big questions, you’ll be able to navigate through dating—and life—with much more ease.

We sincerely hope this toolkit will support you in your journey—and we’re right here with you along the way. If you have any questions or thoughts that weren’t addressed here, we’d love to hear from you at or on IG at



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