The Dean Dsouza Mindset

Date verb {Meet}

to regularly spend time with someone you have a romantic relationship with


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There’s no doubt that the exponential arrival of technology has changed many aspects of human connectivity, including dating. As older millennials, we grew up with a very different idea of what dating was and how it was initiated. We were the first generation to test out dating apps, which were initially simple and harmless but gradually boomed into one of the most popular app categories on the market.

To be frank, those apps depress me. Their goal isn't to help you find a genuine match; it's to extract as much money and screen time from you (which is the case with many apps these days). It has become very much a numbers game, a chance for men to make their moves and for women to sift through countless options and seek validation.

At its core, online dating has turned into a game.

If you're a man, you find yourself competing against countless other men, fully aware that conventional beauty standards heavily influence your results. If you don't fit the mold of conventional attractiveness or if you belong to a race or class that is often looked down upon (anyone who isn't white, for example), the app isn't designed to optimize your chances for success. Instead, you're more likely to encounter women who may seek to take advantage of or dismiss you, rather than finding genuine connections (speaking from personal experience).

For women, the experience often involves having an overwhelming number of options, but rarely ones that are truly desirable. Conventional physical beauty standards also play a significant role here, as does the likelihood of encountering creepy or undesirable men who are primarily interested in casual sex. An unintended consequence of being deemed attractive is the development of a false sense of confidence. The TV show "30 Rock" aptly captures this phenomenon, referring to it as 'The Bubble'. It portrays how attractive individuals receive more favorable responses from the general public.

Soon enough, I came to the realization that online dating wasn't yielding the results I desired. That's not to say I didn't invest several years trying to make it work. However, at a certain point, I recognized that this wasn't the path I wanted to take in finding someone special.

So, what approach resonates with me? What works for me?

Well, I consider myself a proponent of old-school romance. I long for the days when the foundation of dating was built upon friendships. Isn't that how it used to be during our school and college years? You meet someone, discover common interests, become friends, and cultivate a connection.

Gradually, you realize your feelings for them, your desire to spend more time together grows, and you gather the courage to ask them out, knowing that rejection is a possibility. But when they say yes, you enter the realm of dating.

I've simplified the process, but that's essentially the essence of countless successful romantic comedies from the past five decades. It's always about the "meet-cute" or sometimes a well-intentioned "set-up." These are the stories my generation grew up on—the likes of The Notebook,The Princess Diaries, Definitely Maybe, and even Deadpool.

Ultimately, all great love stories are, at their core, captivating narratives.

And it's not to say that dating through apps can't also lead to an interesting story, but personally, I prefer minimal technological app involvement in my own dating journey.

So, why doesn't conventional dating advice work for me?

Firstly, when I tell people that I don't use dating apps, they are often surprised. Common responses include, "Then where do you meet people?" It seems that the prevalence of technology has clouded our memories of a time when meeting others didn't rely so heavily on apps.

Dating apps, although extremely commonplace now, weren't a prominent thing just a decade ago (which, in the grand scheme, isn't a long time). I remember when one of my closest friends met her current husband through Tinder, and it was a novel concept for many of us at the time. This technology is still relatively new, and it doesn't work for all of us. As an introvert, I prefer taking a more gradual approach.

Furthermore, people may not realize how old-school dating differs from modern relationships.

One key aspect is the emphasis on communication. When you meet someone through Bumble or Tinder, there's an expectation of a romantic context even before the meeting takes place. You enter the interaction with a preconceived notion of what the relationship could potentially lead to.

In old-school dating, you discover those expectations together. For those of us who grew up in the '90s, we remember that building relationships didn't start with sending explicit photos or engaging in sexting. It began with friendships and gradually evolved into dating. That's the approach I prefer now—building strong, non-sexually based connections that ideally last a lifetime. And that... takes time.

Yes, people are busy and time is valuable, but the end result is a relationship that is more likely to endure. Even if it doesn't, there's something worthwhile to salvage from the experience.

Old-school dating keeps you grounded and connected to a smaller, more meaningful dating pool. You understand that you'd rather have five deeper and more significant connections built on trust than a hundred hollow relationships with online profiles. Your focus is on your intentions with your partner because you have something real to lose.

Competition isn't a major concern for you because you know what you have to offer—something genuine. Your challenge lies in overcoming your own insecurities and gaining the confidence that your bond is stronger than any superficialities.

Dating advice from someone who relies on dating apps doesn't resonate as effectively with an old-school romantic. The approach of an old-school romantic involves putting in a lot of effort and being willing to make a fool of yourself. It's about self-discovery and having self-worth that isn't dependent on filtered pictures or catchy bios. If you're someone who doesn't enjoy using dating apps, you won't find value in advice from those who do.

The insecurities associated with dating through apps are completely different. With apps, the focus is on getting matches, having attractive profile pictures, and navigating through endless textual conversations that often lead nowhere.

In the pre-app era, the focus was on breaking the touch barrier, effective communication, interpreting body language, and understanding what the other person desires.

The core essence of dating and finding a partner is unlikely to change. It has worked for generations and will continue to do so. However, the way we find people through the filter of technology, with superficial profiles and disappearing messages, takes away from the social component of simply falling for someone. It takes away from the experience of going out and meeting your future partner in unexpected environments.

What I'm truly beginning to appreciate now is the joy of the dating process. Online platforms often highlight the horror stories and portray the dating scene as difficult and challenging, but embracing the old-school approach reminds me that dating used to be enjoyable. It's about meeting new people, engaging in activities together, creating memories, experiencing a range of emotions, and navigating through the exciting and sometimes confusing journey of discovery.

I understand that dating apps are increasingly dominant, and it can be challenging to find someone who still wants to embrace the old-fashioned way. But I believe it's worth sticking to your principles. The return on investment in terms of meaningful connections is well worth the occasional stumble. And at the very least, you'll have some fun stories to share and a boost in self-confidence. Dating is a process, and when you engage in it with an open mind and a positive attitude, it can be a genuinely fun experience.