An Affair To Remember: A Guide to Dating Yourself

Tulips Flowers” by Alisa Anton/ CC0 1.0

“Science and philosophy are for living. If you understand how your brain works, you can architect your life for the better.

Dr. Lisa Feldman Barrett

Consider this the next time you have a few moments of peace: do I want my life to be remembered for what I did? Or do I want my life to be remembered for what I didn’t do? Two very different questions. You can be married but realize later it was not the relationship you should have pursued. You can be at the top of your game in your profession but not a job you’d aspire for again. It is usually in the end that we realize that the practice of self-mastery was the key to living a fulfilling life.

It is through my own philosophical journey over the last 7 years, practicing Stoicism, that I have started to focus on what I want my personal legacy to look like. So today, I share this concept with you. An affair to remember. Why dating yourself can be one of the most meaningful things you could ever do in your lifetime.

The greatest ongoing love affair you will ever have is the love affair you have with yourself

Regina Thomashauer

That’s right! Woo yourself Boo Boo! Dating yourself is just one of many untapped opportunities for self-examination, whether you’re single, divorced, separated, widowed, or even married. Self-mastery is the ability to fully take control of your own life. It is so much more than knowing your wants, but also what sets you off, what makes you uncomfortable, what motivates you, and most importantly, the definition of what your needs truly are. Yet in a world where you are always connected and living on autopilot, opportunities are being missed every day to design the life you deserve.

This article deep dives into the concept of “An affair to remember”. The benefits of dating yourself and offers a few date ideas to get you interested in dating you. Bow Chicka Wow Wow!

*External links are being provided as a convenience and for informational purposes only; they do not constitute an endorsement of any of the products, services, or opinions of the corporation or organization, or individual.


Embarking on a new relationship whether it be with an actual person or yourself can be a rewarding journey, but one that requires a couple of things to consider first.  


For people in recovery from substance abuse, the acronym H.A.L.T. was created by addiction counselors as a system for users who are working to stay “clean” to use to check in with themselves. These four triggers, hungry, angry, lonely, and feeling tired are enough for someone in a vulnerable state to make a poor decision.

In efforts to learn yourself better and assessing why you choose the partners you choose – I too came up with an acronym for you to use as a system check-in.

Sometimes we don’t necessarily choose partners that are good for us especially when we are in a downpour rainy season in our year. We then end up choosing a person for their warm body instead of their warm character. Alternatively, if we are in a relationship that is lacking something we need or do not feel our partner is giving us, that could also place a person in a dangerous spot; whether we are thinking about infidelity or some sort of vice to make us feel better quickly. What it ultimately comes down to is looking into ourselves, and dating ourselves, before we give in to another or to vices that don’t serve us.

So what’s my system? Consider telling yourself H.A.L.O!!!! When you are feeling these emotions/vulnerabilities: Horny, Anxious/Irritable, Lack of focus/interest in group outings, Overwhelmed/Overstimulated, it may be time for some YOU time!

After getting a feel for your emotional or physical needs, in preparation for dating yourself, it can be helpful to ask yourself questions about your expectations from your love interest.


How do you wish for a partner (a future potential or your current) to respond to you when you want to spend time with them?

There is this cute Instagram reel that was circulating a few months ago. This adorable wife walks into her husband’s home office and he is sitting in his chair working on the computer:


After that, let’s snuggle and rewatch every season of Outlander 💃🏻🕺

♬ original sound – Thedashleys
You can view this video on Instagram @thedashleys

Wife: Hey, ya busy?

Husband [answers sincerely and enthusiastically]: No!!! You hungry? Wanna go somewhere?

Wife: YAAASSSS!!!!

Husband: Should we get dessert, maybe we should get two desserts? I found the cutest nature trail. On the way we can hold hands! Any farmer markets on the way? Maybe we can stop at Barnes and Noble while out. Hey, we can hold hands there too!!!

Throughout his entire rant, picture his wife jumping up and down, air kicking out of excitement and even opera singing into the air as he says all the right things.

This scenario although not a total pipe dream, is a rare occurrence. So as you continue with this guide and consider my date suggestions I want you to view yourself as your potential partner. Be curious about yourself. Be intrigued with yourself.

Just as that husband said all the right things to his wife— say the right things to yourself.

Let’s explore the benefits and some dates to not only try but to reflect on and possibly diary about as you get deeper into this new relationship and the infatuation of this person you call Self.


The idea of spending time alone can seem daunting and even uncomfortable for some. However, research shows that investing time in yourself can have numerous cognitive benefits, including improved self-awareness, an increase in self-esteem, and reduced stress levels.

Regina Thomashauer explains in her book “Pussy: A Reclamation” that it’s important to take the time to understand ourselves, our wants, and our needs. By relying on others for things like massages, back rubs, or even orgasms, we give away our power to others. This can lead us to make poor choices in actions or people because we believe they will fill a void. However, these temporary fixes only scratch the surface of our deeper needs. It’s crucial to recognize that our well-being should come from within, and we should take responsibility for our own happiness.

Furthermore, when we deprive ourselves of pleasure, it can have serious consequences, similar to decision fatigue. It leads to poor decision-making and negative emotions like anger and resentment towards loved ones and everything around us. This can leave us regretting how the things we worked hard for didn’t last forever, only realizing this on our deathbed. It’s important to expand our identity and not attach it to any one person or thing. Having this kind of awareness and control can be life-changing. Remember, you only get one life.


Every woman can write her own story of partnership, which is an ongoing adventure.


Your level of self-awareness in the things you think you want is where your power lies. Think about it, you just had an orgasm an hour ago so you’re not going to fall into bed with that Putz. You’ve pampered and massaged and honored your body over the weekend – you don’t need him to tell you how fucking sexy you are, because you are going to tell him how fucking sexy you feel.

Besides, how many times has a partner told you how beautiful you are in the morning, how sexy you are in your essence of messy hair, don’t care…and for what? You don’t believe them anyways. You crave wanting someone to make you feel that, but in all actuality, you don’t let their words penetrate you. Do you know why? Because it is an absolute lie to think to yourself that someone else is going to validate your worth. Well, guess what? You don’t have to wait till you reach the end of your story, thinking “Omg, that was so fucked up”. Because I am here to tell you now, everything starts with you.  

“We can never get enough of something that almost works.”

Peter crone

As time goes on and you get used to dating yourself, you will start to realize it is so much more empowering to know that you don’t need someone (the way you think you do), rather—you want them. You want them because they are hilarious. Because they have the same interests as you. And to have them join you to experience an amazing life together, not because you are in an emotionally impulsive state and the other person looks like a yum yum chocolate chip!


Cook yourself dinner

With intention. To cook a delicious dinner, start by setting up a playlist or choosing an album with music that matches your mood. Some of my personal faves, ( on apple music) for a jazzy, New Orleans feel, try Sidney Bechet. Alternatively, French rap music such as Gazo’s “Rappel” or Sirine Jne’s “Plus Besoin” can be great choices.

Once you have your music, pour yourself a drink and start cooking. As you move around the kitchen, imagine watching yourself in awe, like a love interest watching a beautiful woman in her zone. Enjoy the process and feel good about yourself.

Buy yourself flowers

Especially on tough days. Divide them and put them in rooms you’ll be visiting. Inhale their fragrance, and appreciate their colors and texture. Flowers are wonderful, and so are you. Indulge in them and activate your brain’s reward center.

Create yourself and alter

Build your own sanctuary by creating an altar with your favorite items such as candles, crystals, or flowers. You can set it up in a corner of your bedroom, on your deck, or even in your closet. Use your five senses to create a peaceful and calming atmosphere that you can instantly look at and feel at peace.

Write yourself a love note or a poem.

Write a love note or a poem to yourself. Share your dislikes, fears, and frustrations, or focus on the things you like about yourself such as your lips or your silhouette. Write a sensual poem about the allure of yourself or write a letter addressing your dislikes and respond to yourself as if you were your own lover. Add sweet nothings, heart doodles, and your favorite stickers to the note.

Give yourself a WHAT YOU NEED Date

What are you feeling? Do you need a nap? A pedicure?  What do you think would make you feel better? Like the wife in the Instagram reel…make that video a reality and go do it!


Having a strong intimate connection with someone can boost our self-esteem by highlighting qualities within ourselves that we may not have noticed before. However, we can also work on improving our self-esteem on our own by intentionally practicing self-growth. While being in a relationship may expedite the process, it is not the only way to achieve confidence and improved self-esteem.

With a little research and creativity, dating yourself can be about pushing yourself out of your comfort zones.

As children, we had the determination to do things regardless of our fears, but as we grow older, especially as women, we tend to lose touch with that trait. However, we can recall our childhood experiences of accomplishing scary tasks that made us feel amazing and boosted our confidence. It’s important to hold onto that feeling and mindset throughout all the stages of our lives

That fire that you once had, that wild child spirit, that unapologetically unrefined presence that made you so irresistible to the people around you—she’s still there!!! After crossing the threshold of discomfort, you will experience her presence once more as she flows through your veins.


Take yourself to out eat.

Go to breakfast alone. Want to snack but not ready to be seen in bright lights… take yourself to see a movie alone.

Join a group.

Take a class or join a group of your interest where you don’t know anyone. Learn a new skill.


Although this may seem contradictory to what I am telling you about solo dating, many studies have published that flirting can be positive for your all round well-being.

When you are flirting, you are having fun! It is a natural superpower of yours coded in your DNA and it allows you the freedom to enjoy the gift of being a woman. So go on and don’t be shy-work on that wink and give your smile a try!

Go on a Fear Date.

Ready for a date like no other??? Fear dates help you to conquer those distorted fears—whether it’s rocking a bold new look, embracing something that you are self-conscious about, or bungee jumping off a cliff. It’s about embracing your individuality and breaking free from old perceptions. Who cares what others think?!?!?


Believe it or not – as rewarding as it can be to be with other people, it can also create stress. Technology also is a fuel to stress and you may not even recognize it. Merely scrolling through Facebook just to “keep up” with what’s going on in other lives can sometimes lead us to feel bad or stressed out about our own life. Not to mention how social media is also now bombarded with ads and news clips in between happy photos of your Facebook friends that also lead to stress on a subconscious level.

As research and studies continue to emerge, it becomes increasingly clear that spending time disconnected and alone can have immense benefits for your well-being. While traditional practices like meditation and quiet contemplation are great for some, they may not be everyone’s cup of tea. As someone who likes to think outside the box, I’m excited to share some unconventional ideas that are sure to inspire and invigorate you. After all, this is about dating, so let’s get creative and explore some exciting stress-busting date options together!


Go F*ck Yourself !

Ha! This definitely shines that phrase in a new light but hear me out on this.  In the book Pussy: Reclamation (I REALLY need to do a book review on this for you!) the author Regina, shares an experiment that she tried on herself, giving herself “an orgasm every four hours during ovulation and menstruation”.

This experiment aimed to explore how a female’s emotions may fluctuate during different times of her menstrual cycle, often leading to uncontrollable outbursts of anger, tears, or erratic behavior. Moreover, during this cycle, there is a higher probability of unhealthy eating habits.

After conducting this little experiment Regina found that her food cravings were reduced, as well as her cramps eliminated while a noticeable change in her moods.

‘…when we are in our “heat” cycle, the body is tumesced—swollen with sexual energy. This buildup of ungrounded sexual energy results in drastic and dramatic mood swings.’ 

She goes on to say that although this roller coaster ride occurs a lot of the time in women in general it becomes stronger during the menstrual time.

So I suggest you do an experiment of your own and do it on other days than just your cycle. Maybe you’ll find yourself to be more in control and in a much better mood!

Take yourself on a tour…

of your vagina! If you are planning on treating yourself to the date experience above, why not make it an artsy kind of date? Not only does the act of self-pleasuring serve as a stress buster but it has the extra benefits of leading you towards self-awareness as well as a way to becoming more comfortable with your own body. Grab a mirror and check it out as you run your fingers across all the areas that make up your vulva and see how it changes colors. How it changes shape even especially when you are turned on. How beautiful it really is.

Buy some new toys or subscribe to porn sites.

Porn, interestingly enough, has come a long way these days with more female-focused (meaning female desire acts) than what most women would honestly expect. (Ethical) Porn sites today like are female-founded sex-positive sites known as “porn for women”.

Not into porn? Look into Dispea which is a site full of lust stories. Like an audible for erotica.

How about some new toys for your toy drawer? We are finally in a place where women are creating products for women and with so much passion and research being put into it there are so many different devices to suit your needs today.

Forest Bathing.

It is Japanese practice— a process that promotes relaxation.

A little date in nature, being quiet and calm walking amongst the trees, taking in all the sights and sounds around you. There is nothing more invigorating than being outdoors whether it be amongst the ocean, mountains, or the trees!   


Maybe you are feeling inspired but you still aren’t sure if any of the above are for you yet. Just remember…there are no rules, and there is no one way to date yourself. After all – you are in charge of this new romance and how you want it to evolve. So take your time.

Start off with just 10 minutes alone and see if you can truly just be with yourself. Don’t change your thoughts but observe them as if you are a romantic love interest noticing an attractive woman (that’s you!) and wondering what is she thinking. What is she about? Who is she? Observe yourself. Be your own curious interest.

Here are a few other simple solos to try

  • Spending time in pajamas
  • Cleaning your home or decluttering
  • Crafting
  • Filling your home with scents you like or that you think smell pretty
  • Canceling plans in favor of hanging out with yourself
  • Taking a drive, windows down , music up!

“Its time to dive in and allow that new version of life to take shape through you…”

bianca sparacino, a gentle reminder

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