Ultimate Men’s Guide to Dating in Your 20s: Part 2 – Strategies for Success

In part one of this two-part series, we focused on the fundamentals of getting your life in order. One thing I’ve learned about trying to master dating and seduction throughout my 20s is that it really doesn’t matter how much you know, faking your confidence can only take you so far if you don’t have the other aspects of your life in order.

If I could redo my 20s knowing what I know now, I would’ve focused more on the five pillars of life I discussed in part one. This would’ve naturally enhanced my self-confidence much faster, rather than learning the best tactics and strategies of dating and seduction first.

If you haven’t gotten started on that process yet, I suggest putting off reading this article until you start implementing the concepts in part one. However, if you already have your life in order, feel good about yourself internally, and you’re ready to put yourself back out there in the newly vibrant post-pandemic dating market, please continue reading.

Transitioning from College to the Real World

In part one, I described some of the struggles I had to navigate with dating after college. One thing I didn’t mention is how common it actually is for a lot of men who enter the workforce and leave the bubble of the college ecosystem.

It’s something that frequently comes up with the 23 and over crowd that sign up for our Dating Mastery Program. A lot of guys who are out of college find it harder to meet girls, so they hit a plateau in their dating and social life and end up getting frustrated. We’re often asked by our younger students, “How do you meet women when you’re a younger guy that’s fresh out of college?”

This period in your 20s is an odd time. Men around this age are making the transition out of the social structures the educational system has provided for them their whole lives, and right into the abyss of independent adulthood.

Unlike women, who hit their sexual peak somewhere between the ages of 21-26 and transition towards settling down into longer-term relationships, getting married, or perhaps starting a family, men’s options with women tend to increase with age, experience, and skill.

While not always the case, many women prefer to date men who are older than them, more stable, successful, and sexually experienced. This leaves some less experienced men at this post-grad age feeling lost when it comes to dating and relationships.

Some guys might think they’re out of options after leaving the college ecosystem and social scene. Some even ruminate on not being cool enough or confident enough, or never feeling like they’re enough to expand their boxes and start taking risks in their dating and social lives.

It also doesn’t help that for a lot of young men around this age, work takes over and their social circles start to dry up due to factors out of their control.

For example, after I finished undergrad, outside of my small circle of best friends that I still regularly talk to and hang out with, a lot of my other friends and acquaintances from college moved away, for various reasons such as work opportunities, getting engaged, or just doing some soul searching.

The regularity of life took over and everyone’s priorities and goals shifted, which is a natural part of life. But don’t be discouraged by this. It happens as we grow older and enter these different stages in our lives.

Think about your peers and friends from grade school or even high school. Outside of the very few that you occasionally stay in contact with and get together with, do you still talk to most of them? Of course not, there’s not enough hours in the day to catch up and keep track of everyone, even with the convenience of social media.

Much like our life priorities and goals evolve as we mature and change with time, it’s the same with relationships. Sometimes our preferences change and we outgrow people as we expand our worldviews and have different experiences.

After almost a decade of teaching courtship and being in various flings and relationships, the girls I used to be interested in when I was in my early 20s are drastically different now. This is due to a combination of experience, wisdom, maturity, and having a stronger sense of identity.

Dating Gets Easier as You Mature

Whether you’re in your mid or late 20s, it’s never too late to learn courtship and seduction. Actually, when I got to the ages of 27-28, I began to realize that the dating game gets better and easier as you get older. But the catch is that you need to stay open to learning and developing yourself, starting with the five pillars of life mentioned in part one.

Sometimes I have to remind myself that even with experience under my belt, the learning and execution never ends. As a man, you get more attractive as you get older, up to a certain point, and provided you don’t slack off on taking care of yourself and keeping your priorities in order.

As I mentioned before, women are often attracted to men who are older, more successful, socially confident, and sexually experienced. So the more experience a guy gets in proportion to getting older, the more his dating pool tends to expand.

To reiterate this point, think back to when you were in the early stages of college. You might’ve noticed that the most attractive girls tended to date guys who had a higher social status, or were a bit older and already out of school, working, and more financially established, compared to the guys who were just starting out in undergrad.

This ties into the concept we teach about attraction in our workshops and programs: attraction is a perception of value. There’s a biological aspect to this, even with all the rapid social changes that have taken place in the last 40-50 years.

Attraction differs for men and women. Men tend to want a mate who’s physically healthy and still at the prime age to produce children. That’s why men unconsciously put a higher premium on physical attraction and looks.

On the other hand, women tend to screen out men based on their ability to provide, protect, and lead. One of the reasons why women are attracted to men who are older than them is because they have more resources, status, experience, and confidence.

Men tend to become more established in their later 20s and 30s, compared to the young man who’s still in college trying to figure himself out and navigate his own masculinity.

This doesn’t mean that dressing better and prioritizing your health isn’t necessary. While I said that women judge a man’s attractiveness on his confidence and ability to provide, don’t take that as an excuse to neglect your physical appearance and health. There are lots of other nuances that factor into attraction and the differences between how men and women approach it, but we’ll save that topic for a future article.

For now, just understand the fundamental concept that as men get older and mature, they become more attractive. Now let’s get into the strategies you can start applying to maximize your dating life.

Nurture and Maximize Your Social Circles

Like most men in their mid to late 20s, you’ve probably neglected your social life due to other life commitments like paying off debt, focusing on your career, and things like getting a car or your first apartment or house.

These things require a major time commitment. Like many of our students who take our workshops, they simply don’t have the time outside of class to go out and cold approach women in bars and clubs and social settings, or even on the streets, which really limits your opportunity to meet women.

I realized this when my responsibilities started to wrack up after college and I didn’t have as much time to go out anymore. Because I was so burnt out from my daily commitments with graduate school and getting my other business off the ground, I would rather spend my Friday and Saturday nights at home sleeping early or doing something to decompress from the stress of the daily grind, like eating a pint of Ben and Jerry’s while watching Netflix, or taking my dogs out for a walk.

As much as I would’ve loved to go on dates or have a girlfriend, I didn’t have the energy or desire to go out because I was so mentally and physically drained. The same issue would come up in our workshops, since a lot of our clients were working professionals and had a list of commitments that put them in a similar dilemma.

This ties into what I was talking about last week in part one about nurturing and putting an emphasis on having a good support system of friends, family, and other men to develop a sense of community.

It’s not even just for your psychological health and well-being to have a community. It makes meeting potential lovers and eventual girlfriends much easier. While I didn’t have the convenience of the college ecosystem to easily meet people and just approach random women with a devil-may-care attitude anymore, I spent a lot of my time after college nurturing my existing social circles.

These circles included my immediate friends, family, work-related colleagues, and friends I met through hobbies and interests. I would carve out small amounts of time during the week or whenever I had some downtime to hang out, grab dinner, or have small get-togethers.

A byproduct of nurturing my social circles (which I discovered by accident) was that I would end up meeting girls through my friends. This made dating in some ways easier, more efficient, and more sustainable during this volatile period of my 20s.

The key is to not go in with the sole intention of meeting women through your friends, because not only would it complicate your relationships with them, but you’ll come off as inauthentic and seem like you’re using them just to get your rocks off.

The reason I “discovered this by accident” was because dating just wasn’t a priority for me at the time. I was more focused on having a good support system and enjoying my relationships with my friends.

Much like focusing on the fundamentals of getting your life in order, it’s important that you nurture your current relationships and create depth within them.

Here’s another important point… There’s nothing wrong with getting friend-zoned by women. Put your pride aside and let go of that preconceived notion that the friend zone is a horrible sexless place that has no benefits. Just because she doesn’t feel the same way about you, doesn’t mean you should burn your bridges.

Quite honestly, the girls that didn’t end up reciprocating my feelings or advances, especially the ones who were in an emotionally mature and healthy headspace, would end up setting me up with their single friends and co-workers. This made the process of meeting women so much easier.

Key Takeaways & Action Steps

1. Nurture your current relationships with your friends, family, and peers.

Go out with them, do activities you’d normally do with them, and be a good and present friend. Without this foundation, you won’t have a base to call home or anyone to have your back whenever shit hits the fan and you’re going through tough times.

Plus you never know, they might have a female friend they can set you up with, or bring you along to an event like a wedding, vacation, or party to expand your horizons.

Just make sure that meeting women isn’t the only reason why you’re taking the time to hang out with them. You’re with them because you love them as your friend, you want them in your life, and the support of friends and family is something you can’t put a price on.

2. Expand your social circles by carving out time for hobbies and interests.

A lot of men these days would probably list working out as a hobby. I’m not saying there’s anything wrong with that, but if you’re like most guys who are into fitness, lifting usually tends to be a solo activity. For some people, it’s a means to decompress from daily stresses, while for others it’s a means to improve their self-image.

If you’re trying to get into shape, I’d recommend joining a group fitness or cycling class, taking up Hot Yoga, doing CrossFit for the serious fitness buffs, or any kind of workout that integrates some form of socialization. Besides getting fit, you’re also more likely to meet women in these environments if you’re being friendly, social, and doing it regularly. You’re killing 2 birds with one stone.

But this rule doesn’t just apply to fitness. It applies to hobbies and interests in general. Get used to doing activities that require you to socialize and that include other people, not just women. It could be a cooking class, acting, improv, art, coding, dancing, singing in a choir, or joining a club of some sort like a local dog owners association or anything else that interests you.

We always say in our workshops to be confident, be social, and be flexible. Expanding your dating pool requires you to socialize, and that means utilizing and maximizing every environment you’re in by keeping social connections and being open to all the possibilities.

You never know where these connections will lead. Someone through one of these avenues may end up introducing you to your future girlfriend. Just remember, don’t simply do these things with the endgame of meeting women.

3. Get involved in your career’s social life.

I want to be absolutely clear about my point earlier regarding work colleagues. I don’t want you to lose your job or put yourself in a position where you could jeopardize your career. A general life rule that gets repeated is, “Don’t shit where you eat.”

So even if you have the most attractive co-workers, don’t try to date people you work with. It usually doesn’t end well, and in this weird social climate we live in right now, as a man you have more to lose by being reckless in the workplace especially when it comes to dating.

What I mean by getting involved in your career’s social life is to assume a leadership position and establish some kind of club or group with your work colleagues. It could be as small as taking the initiative to host a happy hour at the local bar with your co-workers. These types of things build camaraderie and make the grind of work more bearable.

Going back to my last point about maximizing your environment, remember that people are an accumulation of different experiences. You have no idea who could introduce you to who, and if they like you enough, who they could set you up with. On the other hand, maybe there’s something they’re struggling with that you could help them with. Down the line, they’ll have your back when you need it.

I may be an entrepreneur, but in my business, we still have little happy hours and abide by the golden rule of “not shitting where you eat.” I can’t tell you how many times on the job I’ve been introduced to single friends of people we’d have a working relationship with that either me or one of my business partners would end up dating, just because we had a cordial professional relationship and an actual friendship outside of the job.

Besides establishing yourself in a leadership position by hosting informal events, or just being a helpful colleague without expecting anything in return, you’d be surprised at what opportunities arise by nurturing your relationships with the people you work with.

The same mindset applies as the previous points: you have to go into this not expecting dating as an endgame. It all goes back to being confident, social, and flexible, as this is another avenue to expand your social circle.

4. Take the initiative and be a leader.

So now you’re probably wondering, “It’s great that I have all these relationships and friends in my life, but what am I supposed to do with all these friends if you keep telling me that I shouldn’t approach it with the end game of dating any of them?”

This is the last and most important point to maximize your dating life in your 20s. Being a leader is attractive, taking the initiative is attractive, and being in a position where you have social status and are efficient with your time immediately makes you a high-value man.

One of the life philosophies that I live by is, “No matter what happens, I just want to bring people together and have fun with everyone I bring together.”

In this post-pandemic and social media driven landscape, relationships come off more as a commodity rather than something that makes the human condition less nihilistic and more vibrant. I don’t think it’s a coincidence that people feel more disconnected, socially withdrawn, anxious, and depressed.

If there’s one thing that makes me cringe in this day and age, it’s seeing “friends” only coming together for an Instagram photo op to give off the perception that they’re actually having fun and enjoying each other’s company for the sake of likes and shares.

I’m sure it’s not the case for everyone, but these days if you scroll through social media, it seems like it’s more of a pissing contest of who’s got the cooler looking friend group or who’s doing the cooler activity. This seems to take precedence over having healthy connections, being present, and actually enjoying your friendships.

I guess that Weezer song holds some truth that high school never really ended and that everything really just is a game of social status and clout. My point is, if you really want to make yourself stand out, expand your social circles, meet women, and succeed at dating in your 20s, you have to be proactive and be the guy that hosts the events.

It doesn’t have to be grand or anything crazy like a Wolf of Wall Street yacht party filled with tons of drugs and debauchery. It can be something as simple as get-togethers in your house or apartment, a movie night, happy hour with your friends, or hosting fun events with all these social circles you’ve nurtured.

As an example, every few months get Korean BBQ and host a happy hour with my friends and work colleagues to celebrate someone’s birthday, a small milestone in their life, or just get them used to getting together and having something to look forward to.

I’ll usually end up inviting a girl I met through one of my hobbies or even on a dating app to come along and integrate her into my social circle. In some cases, one of my friends would end up bringing one of their single friends along to hang out. If we end up going to happy hour, it’s also much easier to meet or invite other women and their friends at the bar to hang out with us and join in on the fun.

I also make it a point to host a party twice a year at my house. I usually have a theme to make it fun and absurd, like a 2000s themed party where everyone has to dress and act like they’re going to their middle school dance.

By mixing and matching all the various social circles I’ve mentioned in the previous points, this not only increased the women in my dating pool as a byproduct, but it’s just fun to be in a position where you can be the guy that hosts fun and quirky little events and get-togethers.

Get Out There

In conclusion, you attract who you are. I’m not saying don’t go out to bars and clubs to meet women. What I wanted to emphasize in this article, much like the fundamentals of getting your life in order, is to maximize every environment you’re in.

I always hear the excuse that “I can’t go out because of so and so commitments.” While that’s a totally valid excuse, it doesn’t mean that’s the only way you can meet and date women.

It won’t happen overnight, but if you’re patient and take the time to lay the groundwork, you won’t have any regrets about maximizing your dating life in your 20s.

As that old saying goes, “Your network is your net worth.” So get out there and start nurturing those relationships.

’Til next time,


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Rob Virges

Hi, I'm Rob and welcome to our website!

In the last decade I've been coaching men (and women) in the art of connecting and finding love. I can tell you I've been referred to as "an asshole with a heart".

Just like other men who've been trying to figure out and understand the dating game, I used to be socially awkward. I'm a former Dating Mastery Program alumni and CofC apprentice with a decade worth of experience under my belt as a student, coach, and lifestyle mentor. My background is in applied psychology and I utilize a combination academic theory, research, and practical application towards our coaching.

I'm not a creepy pickup artist. I'm a normal guy that's competent, confident, and comfortable with women. My job is simple and that's to understand, nurture, support, motivate, and help you achieve and possibly realize the best version of yourself so you can authentically express yourself, connect with women (or men), and help you achieve whatever your dating goals may be in the most holistic, comprehensive, and practical manner.

Welcome to Craft of Charisma, The #1 company for teaching people to authentically connect, love, and nurture healthy relationships that can last a lifetime.

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