Top 5 dating mistakes I made in my early 20s (As a shy guy)

Put your hand up if you are in your early 20s and you're making rookie mistakes with the women you're dating but have no idea how to stop it.

This is where I enter the chat...

Being a shy guy towering at 5'-8" tall with a dash of social anxiety was challenging AF when trying to bag attractive females.

For some context... let's go back to the early 2000s during my high school years.

Here are some nostalgic moments from that golden era:

• The 9-1-1 terrorist attack on the Twin Towers in New York happened

• 50 Cent dropped the classic “Get Rich Or Die Tryin” album and sold 10 million records, all while suffocating Ja Rule’s career

• Most teenage boys rocked Phat Farm or Rocawear clothing with a matching fitted or trucker hat and Nike Air Force One sneakers.

• Michael Jordan was dazzling his fans for the last time as a Washington Wizards player in the NBA

• Your favorite celebrities were getting PUNK'd by Ashton Kutcher weekly

• Justin Timberlake thoughtfully exposed Janet Jackson’s right tidday at the Super Bowl halftime show.

As you were soaking up those moments, I was becoming acquainted with the dreaded friend zone, to the point that I started feeling like an inmate, sorta like how Suge Knight feels in jail right now.

I lowkey blame my mother, aunties, and close female cousins to be honest. Being respectful around them 24/7 indirectly made me appear very soft and gentle around the females I was attracted to, and those traits were not sexy at all at all.

My fellow friend-zoned brothers can agree with me here.

I refuse to believe I was the only guy who took the back alley route to her heart by being her friend first, instead of walking up to her and putting my feelings out in the open like a real G.

Guess what?!

This is a top 2 approach for landing in the friend zone…and it ain’t #2.

Fast forward to my undergrad days in university at age 21, I entertained a small roster of girls who liked me but they were not my cup of tea (respectfully).

I found myself crushing on 3 females that were outta my league on campus (at the time).

I struggled to understand why TF didn’t give me the time of day like they did other dudes.

Then.....

One night after class, I was at the university gym and this sexy brown-skinned baddie from Toronto (1 of the 3), approached me out of the blue, we hit it off, exchanged numbers, and quickly became friends.

Lol I guess all my creepy gazing paid off (I'm kidding).

You can imagine how shocked I was because damn near every dude on campus wanted to be with her, and by some miracle, she took to me.

As we went out on dates, she made me feel important AF because I wasn't used to being in the presence of such a "baddie" (as shallow as that sounds). I won't front, that I had a major crush on her, similar to how Steve Urkel crushed on Laura in the "Family Matters" TV show.

This crush proved to be detrimental because the longer we hung out the more I pedestalized her, and it was to the point where she felt out of reach.

It caused me to have a fear of loss and it affected me in these ways:

• I would have previous plans with friends but the moment she asked me to go out with her, I would cancel all my other plans without hesitation to avoid disappointing her or reducing the momentum we were building.

• Whenever I saw her talking to other dudes on campus or waiters at restaurants etc, a wave of jealousy would come over me and I would zone out because I would think that she's feeling them more and she's gonna leave me in the dust.

• I remember one time we were alone in my dorm room watching a movie Lol this was before Netflix and Chill was a thing btw. The laptop was between us on the bed and I was confident to make a move because I didn't want to mess up and be the laughing stock for her and her roommates.

Needless to say, she forced me to look within and change my ways so I could morph into a composed and comfortable man around the women I date moving forward.

How does the dating game work?

I won't even hold you, I was a late bloomer to the dating game and when I finally jumped into it, I thought it would play out like the movies I saw on TV.

In Hollywood scripts, the producers paint a picture as if the dating journey is filled with a whole lot of excitement, a tad bit of nervousness, and a happy ending where the man and woman find love and ride off into the sunset.

We can see this reflected in classic movies like 'The Notebook', 'Pretty Woman', 'Love Don’t Cost A Thing', 'Love And Basketball, and even 'Crazy Rich Asians' to name a few.

For me, it was a daunting experience riddled with rookie mistakes and missed opportunities in my early 20s.

This is the sequence of actions I wish I took starting in my early 20s:

1. Scoping Out the Scene: The dating process often begins with initial attraction. This sparks physical appearance, shared interests, or mutual friends.

2. Breaking the Ice with: Once attracted, one person typically takes the initiative to make contact with the other (9/10 it is the man). This could involve asking for a phone number, sending a message on a dating app, or approaching in person.

3. Getting to Know Each Other: The early stages of dating are all about keeping it chill and sparking up conversations. This involves asking questions, sharing stories, and finding common ground.

4. Planning Dates and Catching a Vibe: Dates can take many forms, from casual coffee meetings to adventurous outings. The key is to plan something that allows for conversation and connection while doing some fun stuff together.

5. Building a Connection: As dates progress, the goal is to build a deeper connection with the other person. This involves being authentic, showing interest, and being attentive to their needs and desires.

6. Seeing If You're on the Same Page: Throughout the dating process, both individuals assess whether they are compatible with each other. This involves considering factors such as values, goals, and long-term compatibility.

7. Deciding what is next: Eventually, a decision must be made about the future of the relationship. This could involve becoming exclusive, pursuing a committed relationship, or parting ways amicably.

If you find yourself fumbling with attractive women, unsure of how to make a lasting impression, fear not...you're not alone.

Benefits of Dating in Your Early 20s

Diving into the dating pool sooner rather than later can offer you numerous benefits:

• Personal Growth - Dating provides invaluable opportunities for personal growth and self-discovery. Through interactions with different women, men learn more about themselves, their preferences, and their boundaries. This holds because if I didn't have an open mind I would have never tested the waters with women of different cultural backgrounds and religious beliefs.

• Practice for Future Relationships - Whether positive or negative, every dating experience provides valuable lessons for future relationships. By starting early, you can learn from your mistakes and set the stage for healthier and more fulfilling relationships down the road.

• Exploration of Preferences - Early dating allows men to explore their preferences and priorities in a partner. This can help them to better understand what they want and need in a long-term relationship with the woman of their dreams.

Dating in your early 20s can be a rewarding and transformative experience.

By understanding the dating process and the benefits of starting early, men can navigate the dating world with confidence and purpose, setting themselves up for success in both their romantic and personal lives.

Remember, it's okay to make mistakes – they're all part of the journey toward finding love and true connection.

5 Dating mistakes to avoid in your 20s (I learned the hard way)

1| Stop being afraid to ask pressing questions

Asking tough questions out the gate helps you to avoid wasting time, so keep the small talk to a minimum.

If the female you’re talking to does not reciprocate your energy or she's flat-out catching an attitude when you ask pressing questions, it’s time to kick her to the curb homeboy.

You know when you and someone just naturally click, it’s similar to when you shoot a basketball and you know it’s gonna go in the net while it’s in mid-air.

2| Stop stalking chicks on social media

Low vibration = thirsting over a woman’s social media accounts by liking every pic or reel and leaving a comment within 0.5 seconds of them posting.

Women view your actions as a red flag because they assume that you don't have a life outside of them.

In other words….It gives off “clingy-ass boyfriend” vibes.

Ironically enough, women are turned on by men who passionately prioritize their goals.

That’s the typa stuff that makes them weak in the knees. Don't sleep on this!

3| Stop spilling the beans on WhatsApp

Your first instinct is to drop all the deets in the group chat as soon as you part ways with her (or even if she's sleeping next to you).

I get it...

I too had this bad habit of this until I realized my boys don’t need to know every single detail between me and her.

To be honest, it’s kinda immature and it makes you look like a chatty patty. Leave some stuff for you and her to hold on to.

So either cut that shit out completely or offer up limited deets if you feel the urge.

4| Dating just to past time

Start loving your own company and only indulge in date nights if you enjoy spending time with that special woman.

I highly suggest you preoccupy yourself with a creative hobby (like cooking, learning an instrument, or photography) or pour time into building a side hustle for extra income.

5| Stop thinking you're too cool to be a gentleman

Being a gentleman is what real men should aspire to be.

If the woman you are dating thinks you are goofy for opening doors or pulling out her chairs, then it’s clear as day that you are out of her league.

Let her go kick it with Pookie & Ray Ray down at the 7-Eleven if she prefers to be treated like a basic.

Alright my Gz, this is another newsletter in the can.

I hope this is helpful to you when you deal with your next baddie.

Thanks for reading and for being a supporter.

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Much Love.

Javito