Men's Guide to Dating in Your 20s: Part 1

Over these last 18 months, despite all the restrictions and limitations put on the things we usually take for granted like social interactions, gatherings, and community, I’ve had more time to introspect and get to know myself better.

My mind has been lingering on how I’ve lived my 20s, and what advice I’d impart to my younger 20 year old self if I could go back in time.

As I reflect on the final year of being in my 20s and what’s happened in this roller-coaster of a decade, I wish I had a guide like this to direct me through those awkward, unpredictable, and chaotic times that often felt like a second puberty.

Our 20s are often romanticized. A lot of people say that if you fuck up this time in your life, you’re pretty much screwed for the rest of your existence. But I’ve always found this perspective quite short-sighted, every time I’d see an article by someone who’s managed to figure themselves out early on and have a smooth ride through their 20s – whether it be in their relationships, career, or other area.

One thing I’ve learned so far is that life and the circumstances you find yourself in are a lot more complex. It wouldn’t be fair to say that everyone who didn’t have their lives figured out by the age of 30 is a degenerate loser who lives in their parents’ basement.

For every fellow millennial man and even the younger generation that’s just about to enter young adulthood, I deeply empathize with wherever you are in your life and whether or not you have it all figured out. Realize that wherever you are and whatever you’re getting stuck with, you’re not alone. With a little bit of patience and learning to let go of your personal story, you’ll start to figure it out.

At 29 years old, I still have a lot of living to do and a lot of lessons to learn. To some people, I may still be considered a kid, while to others I’m a young adult that doesn’t really know any better. But that doesn’t mean I don’t have any self-awareness or wisdom to share.

I may not have unlimited amounts of energy or that feeling of being indestructible like the 20 year old version of myself. However, in exchange for feeling vulnerable and making a lot of mistakes both in my dating life and professional life over the years, what came out of it was wisdom and emotional maturity.

In this article, I’ll be sharing some pieces of advice and a practical framework for every young 20-something trying to make sense of this decade in your life that’s often romanticized, but in actuality, is quite chaotic, unpredictable, and at times a roller-coaster.

Focus on the Fundamentals

During the pandemic, I had a lot of time to reflect, prioritize, and slow down. While I may not have been diving into another work project and socializing with friends and family like usual, it was one of those rare opportunities that pushed me to go back to getting the fundamentals of my life in order. To paraphrase the wisdom of Jordan Peterson, “Before you criticize the world, clean your room.”

Even though I had finally completed my master’s degree and offloaded some major commitments in my professional life, my personal life was in shambles and I had a lot of personal demons to deal with.

While I couldn’t attend any kind of therapy or be around any type of community due to the restrictions of the pandemic, I spent a lot of my personal time reading and diving back into my passion for fighting, training in boxing and mixed martial arts.

I was lucky to have a punching bag and an instructor who was willing to get on FaceTime with me a few times a week to help me maintain my sanity.

One of the lessons I picked up that has stuck with me through both the good and bad times is: “Focus on the fundamentals, experience it, and master it. Without the basics, there’s no such thing as advanced.”

It may sound simple and obvious, but that lesson really makes me think about all the times in my life where I felt stuck, lost, and isolated. It makes me think about everything I tried to master, or everything I felt inadequate about but would try to find the next glamorous and flashy solution for. It even makes me think about the failures I experienced in my dating life in my teens and 20s.

I’ve realized that even with an advanced degree in business and a lot of entrepreneurial experience under my belt in the last decade, I never really took the time to focus on the most obvious things in favor of the flashy, gimmicky, and “new” things to really figure out how to navigate the three pillars of a balanced life:

Health
Wealth
Relationships

I would chalk it up to being impressionable, naïve, and young, but that’s part of growing up and making sense of the world around us. Even in this world we live in that’s filled with quick fixes and instant gratification, the fundamentals are always an afterthought and rarely emphasized.

By applying this mentality of what they call in Zen Buddhism, “A Beginner’s Mind” into every aspect of my life, I’ve managed to build up a lot of momentum in those three areas of life.

That doesn’t mean I’ve turned into someone like James Bond or the Dos Equis Man. But this simple and radical idea has taken away a lot of the anxieties and fears I’ve had about the future and getting older by simplifying and focusing on getting the basics right.

There’s a saying that who you are when you’re 25 is who you’ll be for the rest of your life. That, I’ve come to learn, especially after 25, is a load of bullshit. In reality, your 20’s are the most tumultuous and ironically the best time to transform and reinvent yourself without looking back with any regrets.

The 20s are a critical period of adulthood where young obnoxious boys become men. Despite the ups and downs, these years are the easiest time to start the lives we want. No matter what we do, these years are an inflection point, a reorganization, a time when the experiences we have disproportionately influence the adult lives we will lead.

Going back to that simple and what I would consider a radical idea, before we get back into the X’s and O’s of dating that you all know us for, it’s important to cultivate the other foundations of your life.

One thing I’ve come to learn about dating, especially in the later 20s, is that it’s much more difficult to prioritize getting good with women and feeling emotionally secure with yourself when you don’t have the other foundations of your life in order.

There’s a difference between when you logically understand something and when you’re actually experiencing it and living it. One of the things we teach in our classes is the idea of nurturing positive feedback loops. Whatever you believe or feel about yourself and current life situation, even if it’s not completely true, will have an effect on your self-confidence and your ability to meet women.

Why Dating in College is Easier

In college and even graduate school, even if you’re not financially stable, from my personal experience it’s much easier to date and meet people because it’s pretty much a bubble and community where everyone around you is in a similar situation.

Logistically, setting up dates was never a hassle. All you had to do was turn to the left or right of you and spark up a conversation with a girl you had class with, join one of the many extracurricular clubs on campus, go to the local college bar or coffee shop, or as many young men would do in the college ecosystem, get involved with a fraternity.

Besides the flexibility in your schedule, dating was much easier because everyone was in a similar situation financially. As I’ve always said to my clients over the years, I’m not the type of coach to paint sunshine and rainbows to you, dating costs money. Whether you’re going out for drinks, coffee, or dinner dates, you end up spending a lot more money when you’re in a relationship than when you’re single.

Dating while you’re still in the college ecosystem is much easier because the combination of being in a similar circumstance, financial situation, and logistics with other peers your age makes it a lot easier to meet and mingle.

Challenges of Dating After College

I’ve come to learn that dating after you get out of college and start working is a totally different animal. Unlike the rest of my peers, I took a pretty unorthodox path after undergrad. I jumped straight into grad school to study business, while also launching a business with a few of my best friends and continuing to coach for Craft of Charisma.

With all these commitments and not having the convenience of being within walking distance of meeting women or having much of a social life as a post-grad, my priorities shifted towards finishing my master’s degree, covering overhead costs, and getting my business into a financially stable position.

Dating and going out with friends took a backseat. Even being able to do normal things that other 20-somethings would be doing like traveling, going out for brunch on the weekends, attending weddings, and going out in the nightlife would be too costly and not a good use of my time.

I’m not complaining, as this is the path I personally chose. However, I’m self-aware enough to admit that these are some of the major reasons why it was much harder to date and meet women after I got out of college.

For the young men who are trying to figure out their dating lives, your current life circumstances really factor into your ability to meet women.

Adulting isn’t easy, and getting into the daily grind of working a 9-5 job really cuts into a good chunk of your time and energy. This only leaves you with the weekends or small pockets of time to keep nurturing your life outside of work.

This ties back to the earlier concept about getting the fundamentals right. Before you start focusing on the best tactics and strategies to maximize dating in your 20s, you have to get the other foundations of your life in order.

One thing I’ve rarely talked about is how much my life circumstances affected my self-esteem and confidence during that period. Between being an entrepreneur, obtaining a master’s degree, and doing coaching, it was a lot to handle.

There were many ways I could’ve leveraged that to my advantage and made it sound cooler and more interesting to the girls I would meet and date. But the truth was, deep down inside I didn’t feel stable or secure. I always had to worry about managing my finances, chaotic schedule, and graduate course load at the time.

As a result, the women I actually did date during that time would pick up on this and would either ghost me or end up moving on to someone who was more secure and stable and in a better life situation.

Good experiences lead to good expectations, and bad experiences lead to bad expectations. This doesn’t even just apply to being in your 20s. In general, not having those foundations in your life will hamper your ability to meet and date women and affect how you feel about yourself.

Social media can also negatively affect your self-esteem, when you’re constantly bombarded with images of people traveling, going to music festivals, buying their first house or car, and seeing people you grew up with in happy relationships getting engaged and married, while you’re still struggling to get by and navigate your young adult life.

Build Up These 5 Pillars of Your Life

In part two of this series, I’ll go more into the practical tips and strategies for dating successfully in your 20s. But for now, I will present a few pieces of wisdom that I picked up throughout my 20s, that will help you avoid some of the issues or problems I had to navigate through, and help you build self-confidence in a sustainable way.

1. Finances

I’m not saying you have to become the next Warren Buffett or Wall Street Bets degenerate and sell the whole farm to make a billion dollars to get a girlfriend.

I’m also not saying that women are gold diggers. If you’ve been reading our content long enough, you’ll know how to screen out and find women who genuinely like you for you.

What I am saying is, get your finances in order so that’s one less stressor or thing to you have to think about when you’re dating.

Invest your time in learning about the stock market. Read and educate yourself on basic finance and concepts around that so you can make wise long term investments.

If you’re working full-time and have college loans or other loans to pay off, focus your energy on offloading any of that debt, and use whatever money you earn to not make insane lifestyle purchases like a Louis Vuitton belt, an AMG Mercedes, or a first class ticket to Burning Man for the time being.

It’s best to make use of this time in your life to offload any kind of debt you’ve accrued and start setting up an ecosystem of income streams so you won’t have to worry about money when you get into your 30s and 40s.

I can tell you from experience, not having that pressure on your shoulders will do wonders for your dating life and your ability to access and date higher quality women.

If you need a place to start to educate yourself on finances, check out this finance book list, which gave me the building blocks to understand the nuances of finance and investing. Patrick Boyle on YouTube also has an amazing ability of simplifying complicated investing concepts and current economic trends into short video clips.

2. Emotional Health

A lot of cliche dating advice for men will prioritize what I call the “paint job approach” such as getting into great physical shape and dressing better, over issues such as addressing and dealing with your psychological and emotional health.

There’s nothing wrong with dressing better and getting your body into shape. These are important pillars to nurturing your self-esteem and taking care of yourself. But they’re always emphasized more in men’s dating advice since they’re quick fixes. As men, we tend to focus more on the visuals and assume this is the end-all be-all of attraction.

There’s more to masculinity than what you look like on the outside. As you mature through your 20s and develop yourself even more, the vanity of looking like a Men’s Health cover model takes a backseat.

I can tell you from experience that there’s a big difference between being macho and being masculine. Being macho and soldering on, especially when you’re suffering internally, may seem like a good solution to overcoming your demons, since that’s what most men in previous generations would do.

But if you’re suffering and ignoring it, you could end up going into some very dark places, and it won’t be pretty. If your emotional and psychological health isn’t addressed, it will really hamper your ability to form and nurture healthy relationships with friends, family, and other loved ones, and especially your ability to nurture a relationship with a woman you’re attracted to.

It’s wonderful that we live in a time now where psychological health is becoming a priority and it’s much more socially acceptable for men to speak about and be open about their emotional trauma and growing pains.

There’s no shame in being open about your pains and traumas. As I’ve come to learn over the years, from dealing with my own issues and coaching men and women from various backgrounds over the last decade, it doesn’t matter where you come from, nobody goes through life unscathed.

Whether it’s emotional or physical abuse from earlier in life, bullying, or a combination of genetics and your environment affecting your psychological well being, these things will manifest and get out of hand if you don’t properly process and resolve them.

If you’re still on the fence about diving into issues related to your psychological health or aren’t sure where to start, I’d recommend visiting BetterHelp to find a therapist.

If you do have health insurance and access to therapy that your insurance will cover, I highly recommend you take advantage and find a therapist or mental health professional that will help you navigate and understand your thought processes and emotions, and give you the tools you need to constructively deal with whatever struggles you’re facing in your life.

I can tell you that even though I had a pretty healthy upbringing and great parents, I still struggled emotionally while navigating my teens and 20s and trying to better understand the pressures of being a first generation Asian American living in the unstable post financial crisis world and figuring out my own masculinity and identity.

I have no shame in admitting that therapy and other similar tools and resources have saved my sanity. They also helped me with cultivating self-awareness and internal confidence over the years, and dealing with adversities in my personal life while navigating my professional life and even the isolation of the pandemic.

3. Community

I came to realize the importance of community during the lockdowns in 2020, when I couldn’t physically be with any of my friends and family when I really needed them the most and was dealing with a lot of things in my personal life.

With the weird social climate we live in today, community among men isn’t emphasized enough. There’s a lot of resentment, self-hatred, isolation, and loneliness that men have to deal with. If you don’t believe me, just visit the controversial Red Pill and MGTOW forums on Reddit and see for yourself. Modern movies have also touched on this concept, such as Joaquin Phoenix’s Oscar winning performance as “The Joker.”

As a young man, even if you’re a natural introvert that gets drained by socializing too much, I cannot understate the importance of having a sense of community and belonging. It does wonders for your confidence and emotional health if you have a healthy group of friends and family that you can lean on, be open with, and trust.

In this post-pandemic digital age, isolation can do a lot of damage to your self-esteem and psychological health. Stats show that the annual age-adjusted suicide rate among men is 13.42% per 100 individuals. Men die by suicide 3.53 times more often than women. On average, there are 132 suicides per day.

I don’t mean to come off as depressing or nihilistic, but before you focus on meeting and dating women, it’s important as a young man to have a sense of community or a tribe of friends and family. Without those social connections, isolation can lead to devastating effects.

Prioritizing your relationships and nurturing your current friend group and relationships with your family is important. If you’re a bit of a loner or don’t have friends or a community to be a part of, or a place to openly communicate your thoughts and feelings with like-minded men who can guide and support you on the journey of life, I highly recommend these resources as a starting point:

4. Physical Health

It may have sounded like I was brushing off prioritizing your physical health in point number two. But I really wanted to address the importance of emphasizing your emotional and psychological health along with nurturing your relationships before getting to this point.

While I’m not a fitness expert, I do have a lot of personal experience when it comes to getting my body and mind in the best possible shape. The point here is not to give you specific diet and exercise instructions. But I will say there’s a big difference between looking good and feeling good, which is directly tied to your self-confidence.

If you’re only working out for the sake of trying to attract prettier women, you’re up shit’s creek without a paddle, and it’s a very short sighted reason to get into shape.

This mental shift came to me around the ages of 27-28. At the time, I was dealing with some major stressors in my personal and professional life. Physically, I looked good and was a lot more muscular, but I was dealing with a lot of nihilism that made me question the point of it all.

I also started outgrowing the gym bro mentality and the vanity and desire to look good to attract women. I’m not saying it doesn’t help, but it’s a fruitless endeavor when you’re in top shape but also dealing with real life issues and not in a good mental or emotional headspace.

Unless you’re a professional bodybuilder or work in the fitness industry and your physical fitness and appearance pays the bills, you don’t need to look like Brad Pitt in Fight Club. On the other hand, if you’re overweight, not satisfied with how you feel, or your physical health affects your quality of life, then I’d encourage you to hire a personal trainer or educate yourself on fitness and nutrition to get yourself healthy.

Notice I said healthy over looking good. I can’t tell you how many times over the years I’ve managed to date women while not being in great shape. I’ve also seen plenty of my out of shape friends get a girlfriend. Even though they weren’t shredded, they felt good about themselves and had their priorities straight, and that confidence naturally sub-communicated through their entire being.

If you’re not a gym rat or find working out boring, try a sport or physical activity that mentally and emotionally stimulates you. In the last two years, I’ve been able to keep myself in amazing shape by taking up boxing and mixed martial arts. While I can’t kick ass like George St. Pierre, it’s a hobby that keeps me mentally and emotionally engaged and challenged, unlike when I used to work out just to look good and for the sake of getting laid.

Ironically, a byproduct of taking on martial arts is getting into sick shape and having a well conditioned and tighter physique. I may not be as muscular or lift the same amount of weight I did when I was in my earlier 20s, but I can move and handle myself in ways I didn’t think was possible before. I also feel safe enough to handle myself in many situations that require clear thinking, focus, and not being intimidated.

That confidence and physical fitness doesn’t have to come from doing martial arts if that isn’t your thing. It could even be as simple as running, hiking, cycling, or playing an intramural sport, as there’s plenty of recreational leagues for working adults.

Whatever you prefer, finding something you physically and mentally enjoy doing will keep you in shape longer, and physical fitness will come as a natural byproduct.

5. Passion

Setting up the proper foundations to maximize your dating life is important. But it shouldn’t just be about dating. Life is short, and if you were lucky to not have lost a loved one during the pandemic, I hope that the downtime last year really helped you put your life in perspective and not take any of your precious time for granted.

None of this is guaranteed. Regardless of your life circumstances or whatever you may believe in, count your blessings and have some gratitude that you’re alive and kicking. Having a vibrant dating life should be a byproduct of living a life you can be proud of and feel fulfillment in.

Everyone including yourself is on a journey, and while this journey can be quite unpredictable, it doesn’t have to be about checking things off a list and following some kind of predestined plan. You’re in your 20s right now, and if you don’t have any of it completely figured out, that’s totally okay.

I can tell you that being a year away from turning 30, and even talking to my mentors like Chris Luna, or my father who’s lived a pretty interesting 60-something year existence, nobody has all the answers or has everything completely figured out.

That’s the point of life; it’s a balancing act. As you grow, evolve, and change over time, your problems, aspirations, and priorities will evolve as you move through the stages of life. Wherever you are right now, that’s okay. If you’re not yet working or earning a living from your passion, that’s okay too.

To give you some context, besides working for Craft of Charisma, which I do enjoy, my real passion is my entrepreneurial endeavor in the fashion industry. It’s unpredictable, dynamic, and filled with lots of peaks and valleys. I don’t love it 24/7 and there are days that I find parts of the job to be mundane, stressful, and frustrating. But regardless of all the challenges, it fulfills me and gives me a reason to get up in the morning.

My point is, you don’t have to be completely in love with your passions. It’s a lot like a marriage; it has its peaks and valleys, but over time you find meaning in it. If you zoom out and look at the bigger picture, you can turn back down the line and not have any regrets for pursuing whatever that passion is.

My best friend and business partner said this to me a while back… It’s not about finding something that makes you happy, because happiness is a fleeting feeling. It’s all about finding something that fulfills you. That’s really all that it is.

When it comes to discovering your passion, it should come from within. I’d recommend you carve out plenty of time to discover and eventually master your passion. You could start off with a curiosity that you’ve been putting off since you were young, or make a list of things that interest you and start exploring each one. Find the one that sticks out to you the most and doesn’t take a great deal of mental gymnastics to get you to do it.

In part two of this series, we’ll go into more of the X’s and O’s of dating. But for now, I’ll leave you with these five pillars. Remember to focus on “cleaning your room” and getting your foundations in order first. Without the proper foundation, meeting women will be a lot more difficult.

Don’t worry if you don’t have all of these foundations in place yet. Wherever you are in your 20s, realize that you are where you need to be. All you need to do is actively and consistently work on getting these areas of your life in order. Before you know it, things will start falling into place.

’Til next time,

-Rob

Blog

Ultimate Men’s Guide to Dating in Your 20s: Part 1 – Get Your Life in Order

Focus on the Fundamentals

Why Dating in College is Easier

Challenges of Dating After College