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Dating in your 20’s vs. 50’s

couple dating in their twenties and in their fifties

7 minute read –

The pursuit of finding love with a romantic partner is a journey that unfolds with time, patience, and usually several different romantic interactions. Often what we search for in our 20’s ends up being vastly different than what we look for in our 50’s. The question is, does either age group do it better?

In the matchmaking world, we get to witness numerous encounters and singles journeys of all ages. A commonality across all age ranges is that the more open a person is, the more success they have. The more compassionate a dater is, the more value they will find from online dating or working with a matchmaking agency. The clients that embark on personal growth, like coaching, while being single, seem to be the ones who have the most transformative and rapid results in finding their ideal partner. 

Love in your 20’s

When you’re in your 20’s, it’s an endless quest for identity, self-exploration, and unforgettable experiences. Change is a constant companion in the 20s — a period marked by fluidity and evolution. In relationships, this means trying to navigate uncertainties in dating with resilience and recognizing that transformation is an inherent part of the human experience. It can be tough, frustrating, and feel much like being on a roller coaster. Though, 20 and 30-something-year-olds should channel their energy into cultivating qualities that contribute to a virtuous and fulfilling life, ultimately laying the groundwork for relationships that are rooted in wisdom and purpose.

Often what we search for in our 20s tends to be more superficial as we put a hyper-focus on a person’s looks, how they dress, what they do for work, where they went to school, how tall they are, and how closely their lifestyle aligns with our own. Being attracted to someone is important, but it’s not the end all be all when it comes to finding a compatible long-term partner. Every person on this planet has come from a different upbringing and life story that’s led them to where they are now. Some people end up coming from wealth, while others struggle to make ends meet. However, who someone is at their core, how they communicate, their values, their drive, and their open-mindedness to the world, their compassion for others, is something that tends to be overlooked or hardly considered when falling in love throughout your 20s.

A lot of heartbreak can happen, and a lot of personal growth, misunderstandings, assumptions, and expectations can be at the forefront of early relationships at a young age. It often takes months if not years to fully uncover who a person is and what they’re all about. Most young daters expect their partners to automatically show up in a relationship being perfect for them and treating them the way they assume to be treated. Not only that but throughout your 20s you are figuring out who you are, what you like, how to strive in this world, all while going through constant change and learning how to be an adult.

woman in her twenties on a date

Love in your 50s

woman in her fifties going on a date

As one approaches their 50s, self-discovery has been going on for a couple of decades now. In the 50s, the focus shifts from external noise to the tranquility found within, ultimately with hopes of fostering a deeper connection with oneself and potential partners. In the later decades, the approach to dating centers on prioritizing values over ephemeral pleasures. What once mattered to a person in their 20s has now shifted to craving more rooted personality traits in a companion, like their sense of humor, adventurousness, family values, and deeper more meaningful communication style or way of conversation. 

By the time you reach your 50s, you likely have a better understanding of who you are and what you want in a relationship. This developed sense of self-awareness can lead to more authentic connections and less time spent on relationships that aren’t a good fit. With life experience, individuals in their 50s often have a clearer sense of their priorities. This can lead to more intentional relationships as you are less likely to waste time on superficial aspects and focus on what truly matters to you.

The emotional maturity that comes with age can contribute to healthier communication and conflict resolution in relationships. People in their 50s may have learned from past experiences and be more adept at navigating the complexities of a partnership. Many individuals in their 50s have established careers and financial stability, which can contribute to a sense of security in a relationship and relieve a lot of pressure. 

In your 50s, the pressure to have children is diminished, allowing for a focus on the companionship and emotional connection in a relationship rather than concerns about family planning. Individuals in their 50s often have a wealth of life experiences, which can provide a strong foundation for shared interests and common ground in a relationship. Shared memories and experiences can strengthen the connection between partners as a path to vulnerability, chemistry and creating a deeper bond.

By this age, many people have gone through the ups and downs of previous relationships. Ultimately, this can lead to a desire for more stable and drama-free connections. Singles may now be better at recognizing and avoiding unnecessary conflicts.

As life passes us by, 50-something-year-olds tend to be more present in cherishing the moments and investing in relationships that contribute to a meaningful and enduring legacy with joined families and social circles.

How To Be Mindful In Both Generations

couple dating mindfully

As our world continues to evolve digitally, it means that the majority of dating and the way we meet people will shift to the online presence. Digital Detoxes are always a great way to get out of the superficial online world and into the real world. Remind yourself what truly matters to you, be mindful of others, and be mindful of your values and boundaries. If we can learn to approach dating with an open mind- in that we seek to value the perspective of others-, rather than judging the life of others, daters will find themselves living in a more peaceful, appreciative place. Gratitude is contagious. We all want to be appreciated, understood, and loved for who we are, so why not practice that with others?

Connection is everything in this world. If you find yourself having a fun, interesting, deep, or loving conversation with another person and you enjoy their energy or presence, then keep the door open and plan another moment just like it. Cherish the opportunities you have to meet unique and different people through dating, but also laugh off the moments that don’t necessarily align with your lifestyle or personal energy. If we can approach dating with a sense of humor, then we can let go of rigid expectations and enjoy our way through the dance of potential romantic partnership. Every interaction will either tell you a story, a lesson, or a blessing. Be grateful for either of them as they also shine a light back onto how you view the world and other people. 

Resilience and personal evolution are key throughout your 20s into your 50s. Not all dates or relationships will lead to the romantic partnership we seek, and that’s okay. By embracing the present, prioritizing compassion, and navigating challenges with resilience, singles can forge connections that resonate with the same energy that they are putting into the world. What you become you attract, so why not become the ideal person you wish to find?

Ultimately there is wisdom to be taken from both generations, though it’s important to note that long-term compatibility often means the simple things in life, like finding someone who makes you laugh, communicates in a way that feels good to you, and appreciates you for who you are at your core. When you find a partner that brings out the best in you and makes you feel like the most authentic version of yourself, you’ve hit the jackpot and that’s something to hold on to.

Jobs will change, money will come and go, and status or materialistic pleasures will fade over time. How a person truly makes you feel is the foundation for building something great with a lifelong partner.  

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