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The Pursuit of Love: Six Lessons I’ve Learned While Dating in My Thirties

The Pursuit of Love: Six Lessons I’ve Learned While Dating in My Thirties

I’ve been contemplating the core of this article for a long while and it has led to considerable resistance and of course, procrastination. But when it comes to the writing process, sometimes a challenge serves as a requisite to execution. The resistance I was experiencing encouraged me to dig within, gain clarity, and move forward with more fearlessness.

Originally, I had planned to create a guide around dating in your thirties. My mind soon wandered to a more specific idea: dating in my thirties as a kinky woman because what in the actual fuck is life right now? But then I thought, let’s be real for a moment. I cannot possibly write a guide to dating when I am in the literal shit of it. If I am being honest, I had recently put a pause on my efforts as an intimacy coach because I began to doubt my ability to help others when my own dating life has been in shambles. But the reality is most of us are in the shit of it. My current dating life may not be ideal, but I have the training and most importantly, the experiences to genuinely connect and attune to my clients in a profound way, to meet them where they are because I am right there alongside them. Rather than developing a guide, I’ve decided to communicate some of the most valuable lessons I have learned as a single woman trying to navigate the dating scene in her thirties.

dating in my thirties

The Desperation for Intimacy Can Cause Us To Lower Our Standards

One of the more difficult lessons I have had to come to terms with is the fact that my longing for intimacy and connection has led me to subconsciously lower my standards. This was a hard truth to face and one that actually needed to be called out by a good friend because I was blind to the role I was playing in my own suffering. As human beings, we all have a fierce desire to connect with others and to be loved, but sometimes, that desire can evolve into a dangerous desperation, and in our pursuit of the need to be loved, we gradually begin to ease up on our value-system. We mistake attention—the most ordinary kind of love—for connection. We neglect the things that are important to us and give into minimal effort because we think we are asking for too much. We wear our hearts on our sleeves and refuse to see the red flags because maybe we can bleach them and dye them pink. We give the benefit of the doubt and make excuses for inadequate partners because well, the sex is fire and we’d rather not sleep alone tonight.

No one intentionally lowers their standards, but when we’ve shared our intimate energy with countless potentials, forced ourselves out of our pajamas to go on just one more date, been ghosted, played more games than the NBA, and have yet to find that one person who makes it all worth it, we can be wrecked by an overwhelming feeling of defeat.

As a result, we lower our standards because we fear no one will check off all of our boxes and we grow so accustomed to lousy treatment that we actually begin to accept it as normal.

But when we do this, we don’t attract the kind of partner or love that we really want. Instead, we attract half-assed love and those vibrating at our lowered frequency. We sabotage our joy by neglecting our needs and we devalue the love—the most important love—we have for ourselves.

Dating, especially as a 35-year-old woman, is not for the faint of heart. And if it’s one thing I am learning every single day, it is that I have to take ownership of my own actions. I have to be okay with admitting that sometimes, I am the problem, that yes, I am attracted to men who are absolutely terrible for me and do not align with my fundamental values. There have been endless instances where I have been too nice, too forgiving, and too invested when I knew damn well the relationship was casual. I have to be incredibly mindful of my destructive behaviors and habits. I have to be so self-aware that I can catch myself lowering my standards for temporary connections. And when it comes to intimacy, I have to remind myself that in order to receive the kind of love I crave, I must believe I am worthy of it.

Dating Multiple People Does Not Make You a Slut

It took nearly two years to dive back into the dating scene after calling off my wedding and I quickly developed a deep shame around seeing more than one person simultaneously. I had this idea that it made me appear too promiscuous, deceitful, or that I was afraid of commitment. But dating does not equate to being intimate with someone and it certainly does not mean you’re dishonest or a commitment phobe. When it comes to women, the idea of dating different men can be a controversial subject because society has trained us to believe that a woman who “roster” dates has a little black book of men they simply call up for sex. But it doesn’t work that way. We are grown and we work hard to protect our energy. Dating multiple people is one of the better ways to discover the kind of partner you truly want, to identify the kind of individual who is actually worth your time and exclusivity.

When I initially began dating, I’d meet someone, put all my eggs in one basket, and feel strong feelings far too quickly only to be let down. This one is different, I’d say.

I had a hunger for replacing old love with new love and in doing so, I was not giving myself a chance to fully understand who I was as a single woman.

I did not give myself the time I needed to explore potential partners and determine whether or not there was compatibility in some of the core areas of my life. It is so easy to lose yourself in infant romance and muddle the distinction between physical attraction and real connection, between chemistry and congruity.

Since opening myself up to dating a variety of people, I have been forced out of my comfort zone and given the opportunity to meet and understand individuals of diverse personalities. I have been able to take my power back, weed out the time-wasters, and smoothen the playing field to those at my level. I have learned the meaning of dating with intention. When you are dating multiple humans, eventually some of them will drop off and you are able to recognize who you genuinely align with. I have indulged in beautiful conversations, enjoyed ridiculously humorous dates, made new friends, and if I’m being candid, experienced both incredible and painstakingly bad sex. But through all of this, I have built an unstoppable confidence and have taken my flirting skills to a whole other level of cheeky.

I think at the end of the day, the most important thing is being your authentic self. Dating is about possibilities. It is about purpose and understanding the significance of your time. It is about being honest with your heart and what it is you are seeking on your journey.


It’s Okay to Apply Pressure

Old me would never ask a man out. Instead, I would stare moon-eyed and optimistic that he’d look in my direction, notice my probably awkward gaze, and slily buy me a second martini. But present me is daring and nothing makes me feel sexier than seeing something I like and going after it with fortitude. When I posted dating polls on my Instagram stories, 91 percent of men admitted to liking when a woman asks them out, yet, far too many of us are hesitant about revealing our interest. We are fearful of coming off too strong, being too aggressive, or not being mysterious enough and allowing the man to chase his prey. But it’s okay to stray from the norm and lean into your remarkable feminine power.

Knowing what you want and acting on it is incredibly empowering and dating is a mutual concession. As women, we are taught the traditional courtship script—men should make the first move, men should initiate conversation or sex, men should pay the dinner bill. But it can be an exciting change of pace when we alter the script and alleviate some of that pressure on our male counterparts.

Asking a man out doesn’t make a woman too forward. It displays a strong sense of self and lets a man know she wants him.

I won’t lie to you, being vulnerable and putting my heart out there has been uncomfortable at times, but I practice compassion. I remind myself that not everyone is for me and that it’s okay. The fact that I am willing to risk rejection for someone I am interested in however, is me giving them a tremendous compliment.

As humans, we are wired to connect with others, to bond, and to love, and rejection is certainly not an easy feeling to process. It can cause us to feel humiliated, unwanted, and unattractive. But why should a woman sit around and wait for a man to get the hint? Why do we overanalyze simple texts and hurt ourselves by creating fictitious stories in our minds about why they haven’t called? There is an exhaustive amount of game playing these days, but I’ve learned that taking a more direct approach not only provides me with a yes or no answer, but it also allows me to reclaim my caliber. I recently asked a male friend what he thought about women initiating the first move and his response was priceless: for the love of God, yes. Please save me from having to do it.

Brutally Honesty Is the Quickest Way To Get What You Want

Honesty is one of the most important elements of a compatible relationship and it is something I have gradually learned to embrace throughout my dating journey. Being genuine and up front with new contenders is not always an easy task, but in every instance that I’ve hid parts of myself, my self-esteem lessened as a result. When you swallow your intentions or tell white lies to satisfy someone else’s standards, you are disrespecting your heart. You begin to lose your light—all those brilliant bits of you that make you extraordinary. Besides, the truth always emerges and closed mouths don’t get fed.

Intentional dating has become an endless activity of trial and error, but I have learned progressively more about myself through every single interaction. These synergies have provided me with illuminating clarity on what I burn for and what I dislike in a partner, the things that intensify my arousal and that which makes me cringe, those who are worth my energy and those who are not. The more accepting I have become of my truest self, the more intimate I have become with my personal desires, and that certainty has encouraged me to approach brutal honesty with ease.

Humans are natural people-pleasers and we conform to different kinds of individuals and behaviors out of our hunger for love and attachment. Being transparent with potential partners has allowed me to become more aware of my feelings and how I spend my time. I have received more respect and appreciation. It has provided me with a newfound freedom and most importantly, it has brought me closer to landing on what I really want.

Being unapologetically honest is a liberating feat. If you only want sex, say that. If you are looking for a relationship, say that. If you’re not feeling the chemistry, fucking say that.

Learn Your Love Language

A dear friend gifted me with the book The Five Love Languages by Gary Chapman as an engagement gift, but it took two years to finally read it. When it comes to books, I truly believe we discover them in divine timing. During this phase of my life I was unfamiliar with the love languages—let alone what mine were—but after delving into Chapman’s words, everything about the ways in which I provided and expressed love began to make sense.

The five love languages include words of affirmation, acts of service, receiving gifts, quality time, and physical touch. While every human has their own unique way of expressing and receiving love, becoming familiar with your individual love languages is essential to cultivating mindfulness and connection. In many instances our brains run on auto pilot and we share love in a standardized way, but sometimes the love we give does not relate to our partner’s needs, and in turn, we can be left feeling disconnected and disappointed. Dating consistently has not only allowed me to define and understand my own love languages, but it has also helped me to reach a deeper level of intimacy by being able to communicate the ways in which I need to be loved.

It is not our responsibility to teach others how to love, but it is our responsibility to be honest about the ways in which we would like to be loved based on our innate preferences.

Recently, I learned that one of my core love languages is words of affirmation. I really enjoy hearing verbal words to communicate love—words of reassurance, compliments or praise. If my romantic interest conveys his love my buying me gifts, I may thank them for the thoughtful gesture, but I would feel a bit dissociated because receiving gifts doesn’t quite fulfill my emotional needs or make me feel loved. Instead, I’d rather hear phrases like, I am proud of you or I feel so lucky to have you in my life baby girl. People are not mind readers and no one will give you what you want if they don’t know what you want. Taking the time to explore one another and determine the ideal ways to connect and express love is empowering. It encourages open communication, enhances appreciation, and allows us to manage our expectations to avoid potential challenges in a relationship.     

Be Okay With Being Alone

Someone once asked me how I could feel so alone when I was going on dates so often. The answer is simple: the dating scene can be one of the loneliest places on the planet. Dating apps can make us feel isolated and deprived of genuine human interaction. Rejection can make us feel uncomfortable and unworthy of love. And casual sex—while instant gratification is often times the goal—can leave us feeling empty and energetically drained.

To be honest, the dating scene is an absolute shit show for women right now and with an overwhelming lineup of apps that encourage hookup culture and replace romance with casual sex, it’s easy to become engrossed in the vanity of it all while still secretly hoping to find our person. We indulge in the endless swinging door of dinner dates, we engage in bad sex for short-lived pleasure—the kind of sex we don’t want to have, but say yes to anyway—we search for parts of those we miss in those we meet, and we date without commitment only to be left feeling confused and heartsore. And when all is said and done, we find ourselves played out, completely discouraged, and once again, companionless.

Learning to be okay with being alone has been incredibly difficult. We are humans and as humans, we are constantly searching for warmth and connection. But getting comfortable with spending time alone and knowing that having a significant other does not equate to my overall happiness or fulfillment in life has been a huge relief. Being with myself has allowed me to become more independent and confident. It has given me the time to really get to know who I am at my core—to meet my messy parts and love myself unconditionally. It has allowed me to explore my body and find pleasure in new and unexpected ways, to be still and hear my own voice, to discover stunning clarity in the fact that I am enough for myself. When you become okay with being alone, you realize a great deal of the love you are fighting for comes from within.

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