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6 Tips for Dating in Your 20s for Guys (Early and Late 20’s)

6 Tips for Dating in Your 20s for Guys (Early and Late 20’s)

Dating in your 20s for guys can be rough.

College is over and women are no longer wholly reliant on meeting men in their classes or from fraternities.

When women get out of college and into the real world, they often find themselves attracted to men who are already established. That’s something that’s great if you’re a guy in your 30s, but will probably suck if you’re reading this and you’re only 23 years old.



Older Competition

Guys in their early 20s are competing against older men who are more established in their careers. They have more money and can take girls out on a full spectrum of dates.

Moreover, they’ve had time to work on their dating game and can most often charm women better than you could due to their experience.

But before you decide to put yourself in credit card debt on dates or hastily try to figure out a way to age yourself 10 years, calm down.

You can sweep a girl off her feet without ruining your credit score or making six figures. My tested dating blueprint has helped tons of guys just like you find success in the dating world.

The emlovz Date Blueprints

Follow this blueprint with each girl that you go out with:

  • First date: The purpose of the first date is to build trust and rapport. This date should be cost around $10. It’s best for this to be a daytime date that is somewhere close to where she lives so that she can feel safe and secure.
  • Second date: The purpose of the second date is to escalate sexual tension. This date should also be active and (praise everything!) FREE! Some compelling second date ideas include things like hiking or visiting a museum.
  • Third date: This is the date where you can loosen your grip on your wallet and take her out for a fancy dinner. The third date is where you both can assess whether or not your morals and values align, and if there is potential for a long-term relationship. The third date is also often when physical intimacy occurs.

When you follow this blueprint, you can show a woman an amazing time without having to feel like you’re competing financially with those older, established guys.

This guide will teach you the ins and outs of dating in your 20’s for guys (early 20’s and late 20’s).

Dating in Your Early 20s: The Options

You have a couple of options when dating in your 20s as a guy and these choices are based on the age and experience of the women you choose to date.

Option #1: Dating Younger

There are obviously exceptions to this rule, but — in general — dating a woman who just turned 21 can come with a lot of caveats.

Understandably, a lot of women who just turned 21 want to live it up as someone who is easing into adulthood but also is extremely young.



When you date a woman who has just been given legal rights to alcohol, they often want to sow their wild oats. This isn’t a criticism to them, just a reality. You don’t want to settle down with someone before you felt like you got all these wild experiences like going out to the club and taking trips to Vegas under your belt.

Women who just turned 21 might not be interested in having a serious relationship for a while. Furthermore, they may not be equipped to handle a super serious relationship since they haven’t necessarily had the experience to navigate their way through a long-term commitment.

Option #2: Date Women Who Are Your Age

Like you, these women are in their early 20s but have gotten the partying and hookups of college out of their system. This could work out very well for you but it also puts you at a disadvantage.

Women in their early 20s often want to date a man who is older because they feel that these men are more established, know what they want and have a maturity that will better align with long-term relationship potential.

Like I said, you have to compete with these guys who have been in the game longer than you and choosing to exclusively date women your own age can leave you exhausted due to that type of competition.

Option #3: Date Women Older Than 30

Allow me to be blunt. It’s going to be really hard to date women who are 25-29, since they are looking for an established man who they can marry in the next 3 to 6 years (most likely). Ask yourself if you honestly think that you are in a place where you can commit to getting married to someone in less than five years?

If you feel that you’re ready, great, but if you don’t, that’s not a criticism. You may want to build your career and do things like save for a down-payment for your first home and become completely settled at a good-paying job.

Regardless, it’s a consideration you need to have when dating.

On the other hand, dating a woman older than 30 can come with a number of benefits and you may find that you’re more compatible with an older woman.

Women who are older than 30 have had more experience in the dating world and have had time to realize exactly what they want in a relationship. They tend to be more established in their careers and aren’t going to be as wooed by a rich man or someone who is way older.

Because of her experience, you may find that you have better, deeper conversations with an older woman, that she is more confident than her younger counterparts, and that she is not interested in drama or playing games. That definitely makes dating a lot more fun and relaxed.

Tips for Dating in Your Early 20s as a Guy

#1: MegaDate

You’re probably wondering right now, “Ok, should I just date older women and avoid women who are younger or my age?”



Absolutely not. Like I said, there are exceptions to every rule, and just because there can be some disadvantages to dating women who are younger or in your age range doesn’t mean you should avoid them. Doing so could keep you from finding a person who would make a great, long-term partner.

What you should do is use MegaDating to date all three age ranges in order to compare and contrast your experiences.

MegaDating is a dating strategy that involves going on dates with several different people at once in order to diffuse energy by keeping your social calendar full.

This dating process is not about sneaking around or being a player — quite the contrary. There is no secretiveness when it comes to MegaDating and it’s not about sleeping around.

MegaDating is something you can use when you are not in an exclusive relationship to see that there really are plenty of fish in the sea and you don’t have to settle for the mediocre when it comes to relationships.

When you MegaDate, your anxiety is reduced, the pain of rejection is lessened and the dating world becomes fun rather than frustrating.

Practice makes perfect, so the more you MegaDate the better you get at interacting with women, which naturally increases confidence.

I used MegaDating during my 100-date experiment when I found myself wondering if love truly existed. I ended up finding a long-term, compatible partner at the end of my experiment and have been happy and fulfilled in my relationship. It worked for me and it can work for you too!

Tip #2: Get In with a Good Circle of Friends

I’m not saying that your college friends aren’t awesome, but are they all the type of people you could see yourself meeting a future wife through?

Expand your social circle and find like-minded people who you can trust to associate with and set you up with a quality woman.

In our program, Dating Decoded, we’ve cultivated a community of men who support each other. Every student in our community is going through the same thing, and they all have the same goal.



They understand one another like no one else does. When you join our community, you’ll gain an accountability buddy, will meet friends in your area (our students are always meeting up IRL), and will gain access to the Man Cave (a bimonthly event where men sit down and talk about their dating lives).

Dating Decoded is really like an extension of the frat or sports team you joined in college. Except you won’t be kicked out the second you graduate. Our community extends lifetime access to all our members.

Our community is on and offline. If you ever have an issue, feel free to get in touch with your accountability buddy, a new friend you met in the group, a coach, or just post whatever is on your mind in the group. Almost instantly, you’ll receive responses offering support and advice.

If you’re looking for a long-term partner in crime, there are a variety of dating apps for serious relationships that are a great way to meet like-minded women.

I recommend my students download at least a few when MegaDating. However, a lot of women like to meet through friends and that will give you an advantage over other men who rely only on dating apps.

Tip #3: Join a Co-ed Sports Team

Meeting women through social sports is a great way to meet women and also get some exercise. A sports team is a great way to meet women without the pressure of having to sit with them interview-style or try to elbow your way into a conversation at a party.

When you choose something active to help you meet women, the activity takes care of lulls in conversation and you also are able to interact more organically.

Simply do a Google search of co-ed adult sports leagues or co-ed social sports in your area, and you’ll be able to find anything from softball to badminton teams.

It’s also a good idea to ask your circle of friends if they participate in any adult sports leagues. If they do, you won’t have to worry about going into the first day not knowing anyone.

Tip #4: Relax and Enjoy This Age

This is a very important tip, so listen up.

It’s great that you are trying to find a relationship, but don’t put so much pressure on yourself. When looking for a long-term, compatible partner — particularly in your early 20s — don’t allow this search to interfere with the energetic fun of being in your early 20s.

Right now, you have just entered the real world of adulting, and there’s no reason to rush from college to settling down.



The older you get, the more responsibility you’re going to have and, consequently, the less fun you’ll probably have time for. Don’t take life too seriously.

Most importantly, if you find yourself struggling in the dating world, don’t beat yourself up about it. Dating in your early 20s can be awkward for pretty much everyone, and you’re definitely not alone when it comes to having trouble with women in your early 20s.

Tip #5: Take an Improv Class

Not only is there potential to meet women who are compatible with you in improv classes, these classes can also help you improve your skills in the dating world.

Improv classes are naturally interactive and teach you skills that you can use in your daily life as well as on your dates.

Life isn’t scripted and there are more than a few circumstances where we need to learn how to improvise. What better way to learn how to think on your feet and not get intimidated by dating curveballs than an improv class?

Improv classes can help you relax and communicate more effectively with women because that’s what you’ll be doing during the class and through various exercises. Another bonus? Improv classes are straight up fun and are basically guaranteed to leave you and your classmates laughing hysterically.

Through humor and creativity, Improv classes teach you how to be playful, which is a big plus in dating. Any class that helps you naturally engage with other in a playful way will help you with dates and life in general, particularly if you have a job that doesn’t allow you to be social, or if you struggle with social anxiety.

Dating in your late 20s for guys

There’s quite a bit of overlap between dating in your early and late 20s.

However, there are some differences to keep in mind.

No First Dates At Party Atmospheres

dating in your 20s

If you’re dating in your late 20s it probably means you’re dating someone around your age. The older we are the more we tend to stray away from rambunctious nocturnal activities.

Don’t get me wrong, you’re still gonna enjoy a banger every once in a while, but it’s probably not the best place for a first or second date.

If you’re looking for a serious partner, don’t invite a Tinderella to a party on a first date.



She’ll think you’re a callow fuckboy more interested in kegstands and other types of stands than a serious relationship.

Tell Her It’s A Date – Dating In Your 20s

Here’s some solid dating advice for 20s-year-olds – be straightforward.

If you want to ask her out on a date, ask her out on a date. 

What do I mean by this?

Far too often men in their early 20s ask women to hang out, or say, hey wanna go out sometime?

The former isn’t a request to go on a date and the latter is too nebulous an offer to be taken seriously.

Clarify your intentions.

Use a TDL when asking her out.

TDL stands for time, date, location.

Here’s an example of a TDL in action:

Hey Jen, let’s go out this Thursday at 8 p.m. to see the fireworks at Harbor Point.

This is a concrete date request she can either accept or decline.



Not only this, but it also uses fairly explicit language. If you want to clarify the dynamic of your outing even more simply add the word date to your TDL.

Hey Jen, let’s go on a date this Thursday at 8 p.m. to see the fireworks at Harbor Point. 

Slotting in the word date makes it abundantly clear that you two aren’t just hanging out or doing something platonic – it’s a date.

Sign Up For 5 Dating Apps

When you were in your early 20s you probably only signed up for one or two dating apps tops.

You didn’t have to sign up for more.

All the women in your age bracket could be found on Tinder.

That isn’t the case anymore.

Effectively dating in your 20s requires you to be on around 5 dating apps.

Why though?

This allows you to cast a wider net and appeal to a range of women.

For example, there are certain Bumble users that won’t use Tinder. 

They think Tinder is shallow, used only by sexists, and is for one-night-stands.

So they exclusively get their swipe on via Bumble.



Each app appeals to a different user.

For men in their late 20s I advise downloading the following apps:

  • Tinder
  • Bumble
  • Hinge
  • Facebook Dating
  • The League

Each app appeals to a unique milieu.

You’re likely to find people on Hinge or FB Dating that aren’t on The League or Tinder.

If you’re not into dating apps you should be.

A 2017 Stanford study showed that 39% of all heterosexual relationships that started that year did so online.

If you’re not willing to meet women online you’re missing out on one of the most happening digital singles parties in the world.

If you don’t know how to get started online, our program, Dating Decoded will show you how.

Dating Decoded

Interested in learning how we here at emlovz can help you?

We teach our students the shortcut to finding their ideal match by MegaDating. MegaDating is our dating philosophy and it shapes everything we teach here at emlovz. Simply put MegaDating is dating prolifically with the specific goal of going on 20 dates in 90 days. This will give you ample women to compare and contrast so you can refine not only your dating skills but who your ideal partner is.

To teach you how to quickly find highly compatible women in just weeks and become the most eligible bachelor in town you’ll have a team of romantic experts, each skilled in their own unique area to support you.



Our Team

  • Emyli (me), co-founder, curriculum developer, head coach, and I host two coaching sessions every week
  • Thomas, co-founder, and coach. He’ll lead the biweekly Man Cave event where men come together to talk dating, bond with one another, and support other single men
  • Cat, Brooke, and Audrey are mock date specialists. Go on a practice date with them (and receive feedback) before your next date
  • Hailey is your new stylist. She’s worked with celebs from every industry and is now about to raid your closet
  • Tilly is our holistic sex & intimacy coach. She’ll help you get the most out of your sex life so you and your partner are happier between the sheets
  • Aundrea is an award-winning fitness coach. Are you ready to eat right and build muscle?
  • Mia is our social media expert. Revamp your Instagram and Facebook profiles with her help and start meeting women online

Our Community

And look, we realize that the single life can be difficult. If accepted into our coaching program, Dating Decoded, you’d be joining a community of supportive men and coaches who are there to listen, support, and encourage you as you navigate the single life.

Our program offers every student a lifetime membership (as if you’ll need it) so the support won’t stop until you’ve found your ideal partner.

If you’re ready to find your forever partner, book a Zoom session with our team today. Together we’ll talk about your dating history, your goals and show you how our program, Dating Decoded, can help you find your ideal partner.

Learn how our students have already improved their dating lives.

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