LESSONS LEARNED IN DATING AFTER 35

By Kimberly Haddad

n February 2017, I was 31 years old and had just said yes to a mar-riage proposal thinking it was the beginning of my forever. But, by July 2018, just four months away from the big day, I called off the entire event. The wedding dress that my mother kept safe for me still hangs in the closet of my childhood home. It is a reminder of a path not taken, a life that could have been vastly different from the one I am living today.

At first, seeing the dress brought feelings of failure and sadness. However, as time rolled on and I pro-gressed from acceptance to healing and growth, those emotions shifted. I never could have imagined the woman I would become or the surprising twists and turns that life had planned for me. All I knew was that marrying my former partner would have only led to heartache and divorce. Now, the dress symbolizes my journey towards self-discovery and advocating for my own happiness. It represents the strength and certainty I had to cultivate in order to end a relationship that was not meant for me, fully aware of the pain that would follow. 

Sometimes, you just get fed up with your own bad habits and ways of liv-ing.It’s that moment when the discom-fort of staying the same becomes greater than the fear of making a change. In my relationship, I always felt something wasn’t right, but I brushed it off until I couldn’t anymore. I read somewhere that our nervous system prefers a famil-iar hell to an unknown heaven, and I’ve seen that play out in my life. We often hold onto what’s habitual, even if it makes us suffer. Calling off my wedding was one of the hardest things I’ve ever done, but it was nothing compared to the grief of denying myself the chance to be true to who I really was. 

At 38, I may still be single, but I have come to appreciate my current state in life. I have committed to honoring my needs, boundaries, and exploring intimacy in a way that feels right for me. The dating scene can be a ruthless playground, and as a woman in my late 30’s, I have faced my own set of chal-lenges and lessons learned. One thing is certain though: I will never settle for anything less than what I want.

LESSON 1: THE EXPECTATIONS OF OTHERS ARE NOT MY BURDENS

Last year, my younger sister got engaged, and although I was genuinely thrilled for her finding such a beautiful love, there was a moment of deep sadness that came with it. During her engagement party, our family and friends gathered for the Hora dance, a tradition where the bride and groom are lifted in chairs. While rooted in Jewish culture, this dance has been embraced by many, including our Middle Eastern background.Watching my sister be celebrated in the air brought tears to my eyes. She’s my best friend and her happiness meant the world to me. But when my dad saw my tears, he remarked, “I always thought you’d be the first to marry. It’s okay, your day will come.” At the time, I shrugged it off with a smile, expressed my love, and continued dancing. A week later, his words came back to me, a triggering moment that forced me to dwell on my own future and feelings of inadequacy. I felt like I was falling behind and that I was unworthy. Thankfully, those feelings passed, but it’s tough not to feel crushed when the expectations of others make you feel inferior.

I used to believe that being in a relationship was the ultimate measure of my value, but I’ve come to realize that my worth isn’t tied to my relationship status at all.I’ve discovered the benefit of waiting patiently for what truly fulfills me, whether that’s finding a life partner or forming a less conventional kind of relationship. Life isn’t about checking off boxes, and there’s no one path to happiness. All I can do is remain true to myself, which requires a great deal of self-love and respect that can easily be overshadowed by outside influences. Finding beauty in practicing patience and resisting the temptation to settle for mediocrity just to meet societal or familial expectations is a powerful act. Oftentimes, we fall into the trap of comparing ourselves to others and feeling pressured to reach certain milestones on someone else’s timeline. This can result in us pursuing goals that aren’t even ours to begin with. I’ve wrestled with this sentiment repeatedly, and regardless of making progress, I continue to struggle with these feelings at times.

Growing up in a large family surrounded by women who walked similar paths, I thought conformity was the only way to be accepted and feel “normal.” However, I quickly realized that this assumption was completely wrong and that the concept of “normal” is multidimensional. The general population often dictates that getting into a prestigious university, establishing a successful career, marrying, and starting a family are the collective norms we should aspire to. These ideals are ingrained in us as the blueprint to happiness. Yet, there are those among us who may not genuinely desire all of these milestones but still find themselves chasing them. In doing so, we risk losing touch with our authentic selves and what truly brings us joy. While goals are undeniably essential, fixating on comparing ourselves to others can stall our progress because we then operate from a place of scarcity and desperation. It is crucial to remember that each person’s journey is uniquely theirs, and our lives unfold in ways that are incomparably singular. 

Right now, I’m not entirely sure about marriage or whether monogamy is for me. I am exploring ethical non-monogamy, or my personal take on it. ENM is a term for relationship styles involving multiple, romantic or sexual connections, with everyone informed and consenting. But I’m not necessarily looking to have physical and emotional relationships with multiple people; I want open communication with my partner and a shared understanding that neither of us should feel confined.I seek someone open-minded, willing to explore new experiences together rather than separately, for the most part. For now, I have a couple of casual play partners and I am dating very different individuals to learn what resonates with me the most. I’ve also made peace with this uncertainty and have faith in the timing and development of my life’s agenda. This acceptance has given me the freedom to further explore my passions and beliefs, deepen my self-awareness, and understand new aspects of myself over time. While I recognize that the pressure can be more intense for women who wish to have children, I know that my future, whatever form love may take, will manifest in a way that perfectly suits me.

LESSON 2: I’M ALONE, BUT NOT LONELY

At 28, I found myself back in Los Angeles after wrapping up an editorial internship with Vice Media in Brooklyn, New York. With no clear direction for my future, I drifted through a haze of parties, whisky, chain-smoking, and reunions with old friends. Eventually, love found me in the form of a five-year romance with someone who evolved from boyfriend to fiancé to ex. Juggling a part-time job at Fred Segal in Santa Monica while residing in my parents’ suburban home, my partner and I eventually moved into a space of our own. This new chapter of sharing one roof brought its tics, notably the shared bathroom—a source of great anxiety eased by my boyfriend’s playful acknowledgment of the inevitable: yes, grown women do indeed poop. Though, truth be told, I still shoo men away when the coffee settles and nature calls. Life was simpler then. Weekends unfolded lazily; we gamed often, shared chores, had a ton of raunchy sex, and spent date nights in cooking pasta. There was no fixed routine in place.

In the aftermath of our significant breakup, I found a new home in a small studio apartment, where I carved out a rhythm that was entirely mine. This transition was the catalyst for my fitness journey, therapy, and provided the solitude I needed to reconnect with myself as a confident single woman. These days, I thrive on my personal vibe, a dangerous state that can complicate dating, or lack thereof. I’ve reached a level of self-assurance and independence that can intimidate potential partners or make it harder to find someone who complements my lifestyle. I greet the day before the sun, with a ritual of sipping coffee in bed while diving into a good book. This is followed by meditation and a workout at the gym. Breakfast is a must, almost always prepared in my underwear before heading out to the office or a nearby café for some writing. Sundays are all about restocking the pantry and prepping meals for the week ahead. And as night falls, there’s nothing quite like smoking a joint in a bubble bath before sleep. I also navigate bouts of depression and oscillate between moods of isolation and intense neediness, yet self-care remains a priority. Whether it’s through journaling, crying it out, deep cleaning, or prayer, I make sure to take care of myself, and I still don’t know how to manage that alongside someone else.

Looking back, it’s amazing how seamlessly I adapted to sharing my space with someone. Yet, over the past six years, I’ve poured my energy into creating a routine that is for me and only me. I’ve learned to be my own protector and cultivate practices that enhance the version of myself I adore.I’ve grown so comfortable with my own company that dating often takes a back-seat to mellow nights in with horror movies—yes, I’m that predictable—and my cat child. My friends joke that my future soulmate will have to track me down at home. But in all seriousness, the thought of living with someone new, sharing a home, and altering my daily habits feels incredibly scary. Any potential partner must enhance my life more than my solitude does for me to consider such a shift. I may be alone, but I’m certainly not lonely.

I have to admit, I can be a bit set in my ways, and sometimes that makes me stubborn. There’s something reassuring about knowing what to expect in a world that often doesn’t cooperate.The life and identity I’ve worked hard to build are precious to me, and the idea of change can be unsettling when there’s so much to protect—and expose. But I’m learning that it isn’t about changing myself; it’s about finding someone who naturally fits into my element. The key lies in finding someone who betters my life instead of disrupting it. When the ideal person comes along, bringing stability, comfort, and trust, they won’t feel like an intrusion, and flexibility won’t seem like a compromise.Together, we can grow and create a life that works for both of us. With the right love, change wouldn’t be something to fear because it eventually evolves into a harmonious togetherness that makes everything feel a little bit easier.

LESSON 3: CHEMISTRY AND CONNECTION ARE NOT THE SAME

The hierarchy of my love languages often changes, and right now, physical touch is at the forefront of how I show love. Alongside this shift, I’ve developed a yearning for more intensity, passion, and deep intimacy. However, these desires can cloud my judgment, especially during extended periods without touch or connection, making it easy to misinterpret chemistry as something more substantial than it really is.

We’ve all felt that intoxicating rush of attraction, the kind of chemistry that lights up the room and leaves you grinning with a pink glow like you’ve just won the lottery. It’s a feeling so great, you might catch yourself on a date, slyly wiping away a little drool while fighting the urge to knock over the entire table and close the gap with a kiss. I found myself in such a moment on a second date recently, where the conversation was just as good as the chemistry. While I was listening intently to what he was saying, my thoughts were consumed with the idea of straddling him in front of the whole bar and feeling the warmth of his lips against mine. It’s in these very instances, though, when I must remind myself to temper the excitement, regain my composure, and assess whether there’s actual compatibility behind the chemistry that first caught my attention.

Navigating the modern dating scene can be disheartening with the regularity of toxic behaviors, ghosting, and emotional detachment. I’ve been fiercely protecting my peace until I find someone who truly values me and reciprocates my efforts. Still, my ongoing single status has time and again caused me to turn a blind eye to red flags, only to be let down when reality didn’t match the potential I envisioned in partners. In the early phases of dating, it can be tough to discern true intentions. It feels like everyone is playing a role, putting on their best performances and saying what they think will win your heart, all the while heading towards their ultimate goal: sex. Yet, as I’ve grown older and had more experiences, I’ve realized that without a strong emotional bond, the physical aspect alone feels incomplete and unsatisfying. I want more. I need more.

In my younger days, I often hurried into sex, seeking validation and using my sexuality as a way to boost my self-esteem. I’ve always felt confident in that aspect. It was my way of feeling valuable, attractive, and desired in a relationship. However, this approach left me feeling detached and unable to experience true pleasure. I did not feel comfortable being my authentic self or voicing my needs, which prevented my ability to relax, let alone reach orgasm.While everything felt good on the surface, it was as if my body was simply going through the motions.

It’s not easy to restrain myself from rushing into sex until I’m sure of a connection that can thrive on its own. But I have become a glutton for the slow burn. In my last relationship, the man patiently waited through 10 dates before I opened the door wearing his favorite color lingerie and climbed his 6-foot-5-inch body like I was a goddamn koala. The days leading up to that moment were wildly unhinged, nearly unbearable if I’m honest.

There’s a unique intensity in the slow burn of intimacy that often gets minimized by the quick sparks of instant attraction. This gradual build-up is like a simmering pot, where each moment, lingering glance, and gentle touch on the leg or lower back adds layers of depth and seduction to the connection. Unlike a one-night stand, the slow burn allows emotions and courting to marinate. It’s in this steady progression that true passion is felt, where every interaction feels more meaningful, and the anticipation becomes as sexy as the eventual embrace. More importantly though, is that this connection feels real, with nothing rushed or contrived. The waiting game is never a chore because mutual respect is always present. And if it’s ever absent, well, that tells you everything you need to know.

LESSON 4: MY NEEDS ARE NON-NEGOTIABLE, PERIOD.

I stand rooted in my womanhood, with a mostly clear vision of what I seek in a partner, my sex life, and my relationships. However, articulating my needs and being upfront hasn’t always come easily. It’s been a journey of hard work and healing. It’s required immense confidence in understanding who I am and loving every aspect of myself, even when faced with rejection or when I’m not everyone’s cup of tea.

I welcome my sexuality and kinkiness, but owning this part of myself brought a lot of shame. It’s not always simple telling a partner about my love for experimenting with pain and pleasure—the sensation of a sharp knife lightly cutting my skin, being whipped with a leather belt, or having my inner thighs slapped at the cusp of rapture. Coming to terms with how much I crave these experiences and the pleasure they bring was difficult to swallow, and this isn’t even half of it. I struggled to love myself for being different. I wanted to be like everyone else, not so complex. It has taken—and continues to take—a lot of effort to overcome the shame and be okay with being me, regardless of what that entails. In the past, however, I often felt the need to hide my intimate desires to fit into the mold of a “traditional” relationship. I feared that being true to myself would push people away or that prioritizing my sexual needs might lead others to label me as promiscuous. I found myself with partners who couldn’t understand or satisfy my needs—sexual or otherwise—leading me to wonder if I was too much. It turns out, I was simply searching for fulfillment from the wrong people. A close friend constantly reminds me that if I exist in all my weirdness, then surely someone like me is out there in this vast universe.I return to this thought when dating starts to feel discouraging.

Through the years, I’ve seen how many of my choices in partners weren’t the best fit, yet I still chose them. I take responsibility for my part in inviting them into my life on the basis of craving connection or the belief that there was nothing better out there for me.But I will no longer sacrifice my needs or water down my true self to gain approval from anyone, be it a man or a woman. It’s so easy for people to alter their personalities and preferences to match the vibe of a potential partner or become who they think they want. For me, it happened subconsciously, sneaking into my interactions before I even realized it. The drive to connect deeply and feel more attractive can be so strong that we dismiss parts of ourselves that might seem too bold, too quirky, or not as appealing. And it’s always a subtle, gradual change that goes unnoticed until we’ve become someone we hardly recognize and feel the extent of our dissatisfaction.

Last year, I made a promise to myself that I would stop pretending. I decided that if I wanted something, I would speak up and ask for it. If I wasn’t compatible with someone, I would acknowledge it and walk away. And if I ever felt unwanted because of any part of who I am, I’d swallow my pride and keep moving forward. I am who I am—take it or leave it.

Dating in my late 30’s has been one hell of a challenge, but it has been mostly rewarding. It all depends on your perspective. Each date, successful or not, offers lessons that contribute to my personal growth and understanding of who I am. I’ve grown more comfortable expressing my current relationship views, whether it’s exploring ethical non-monogamy or building a unique partnership that serves both me and my partner. It’s freeing not to care if others disagree or fail to understand. After all, it’s not their relationship to understand. I’ve become good at reading people and quickly gauging if we might have long-term compatibility. Sharing parts of myself that once made me uneasy has become easier. The last man I dated—the one I playfully scaled like a koala—took me as I was and encouraged my authenticity. When I first opened up about my involvement in sex work, I feared it might scare him away or change his view of me. But he reassured me and said, “You are your own person and had a life before I came into it. I accept you and would never judge your choices. It doesn’t change who you are or why I love you. I want you to be your purest self.” Although our relationship ended primarily due to our age gap—he was 13 years younger—his acceptance made me feel truly seen and unconditionally loved.

When it comes to finding the right person, there’s a comforting truth to hold onto: you can never be too much. The things you think are weird, your dark sense of humor, and your wild expressions of sexuality are the parts of you that the right person will fall head over heels for. They will see your individuality as a treasure, not a burden. You cannot lose something that is truly meant for you.

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