Dating In Your 20s For Guys – Tips & Advice For Surviving Your 20s

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Let me start out by saying that there’s no easy way to encapsulate what dating in your 20s for guys is like.

Or, for anyone for that matter.

Your 20s is a time of immense change.

You’ll change physically, mentally, and potentially enter a whole bunch of different life stages that can all mix things up quite a bit.

In other words, this decade of your life can be a bit of a shitshow.

But hey, that’s alright!

After all, dating in your 20s can also be a lot of fun, and you’ll never know if something is worth it unless you try!

So, time to share a few of the experiences and observations I’ve made over the years about dating in your 20s and some tips to make the most of it.

I’m not an expert by any means, and I have my share of failed relationships and awkward encounters.

But hey, from one random 20-something-year-old dude to another, let’s get into it!

How To Start Dating In Your 20s

I always cringe when I see headlines or “dating guides” that break down stuff like “how to start dating” or “how to find the perfect match” sort of thing.


The reality is, there isn’t a cookie-cutter solution or magic trick to solve this.

However, I think there are a few themes and tips worth keeping in mind for starting to date in your 20s as a guy.

1. Younger…Older…The Same Age?

One really distinct I noticed as I entered my 20s was that a lot more dating options opened up as a guy.

Like, when you’re 18, you can pretty much only date 18 year olds.

When you’re 19, it’s also kind like that.

However, as you get into your 20s, you’ll find that it’s more socially acceptable to date a few years down (I guess women think we’re mature and stable, or something).

On the flip side, you can also start landing dates more easily with women a few years older than you.

And, finally, there’s always your fellow 20-something-year-old peers.

So, my first tip for dating in your 20s as a guy is to decide what you’re comfortable with and what your priorities are.

If you’re still a party animal or in school, dating younger might be fine. If you’ve always felt more mature, older could work.

This isn’t really a major tip, but I think it’s worth some self reflection.

2. Develop Hobbies

I’ve always thought that a sign of successful teenagers is that they have hobbies.

The same is true for dudes in their 20s.

And no, I’m not talking about that hobby of devouring medium pizzas in your basement while playing the latest Call of Duty.

I’m talking about hobbies where you actually meet like-minded people and expand your circle.

Go to the gym, get into biking, join a local volunteer group…do something!

This is hands down one of the most popular ways I’ve seen dudes my age date…a co-ed intramural sport, college club, the gym, or some type of hobby is just a great way to meet people!

3. Try Dating Apps

If you’re wondering how to date in your 20s and just can’t seem to meet people, you can always give dating apps a go.

Apps like Tinder and Bumble are, frankly, the easiest way to score a coffee or drinks date…all from the comfort of your own home.


My advice here is to avoid spending money on these apps and to not waste too much time on them. However, they’re an easy way to at least get your foot in the dating game.

You can also try apps like Hinge if you’re a bit more serious about the dating game!

4. Focus On Yourself

One of my best friends actually said something pretty accurate a couple of months ago.

He said “honestly, once I started focusing on what I wanted to do with life everything sorta just worked out.”

This is a shockingly accurate life philosophy that I’ve at least seen happen a bunch of times.

There’s something weird about actively hunting the dating life that just seems to doom people for failure.

Like, we’ve all seen the creepy dudes at clubs or the guys who are forever unhappy unless they have a girlfriend.

This isn’t healthy behavior.

While it might sound counter productive, sometimes, the best way to start dating in your 20s as a guy is to just become happier and better by yourself.

So, go to the gym, hangout with friends, travel, and do cool shit. You’ll meet the right person in the process.

Tips For Dating In Your 20s For Guys

If you’re starting to meet people and are going on multiple dates, that’s pretty awesome!

However, if there’s one thing I’ve learned from the last few years of being single it’s that there are a few tips that can make your dating life easier.

1. Always Be A Gentleman

I think the world of dating apps and social media in general has made dating in your 20s almost a bit more cynical.

I mean, people can basically order dates these days like they order a pizza. In my opinion, this makes it easy to forget that we’re dealing with real people here.

Regardless of how messy your dating life gets, you always have to be a gentleman.

Treat people with respect, be upfront/honest, and do your best to make sure both parties are always having a good time.

2. Know That Life Stages Change

One of the biggest things I struggled with in my early 20s (while in a serious relationship at the time) was that life stages change.

I think this is a common reason why people break up. It’s why I did, anyway.

See, oftentimes, dating in your 20s starts in college, or during your first full-time job.

This inherently means that, if you stay together with someone you start dating in your early 20s, you’re going to go through a lot of change together.

And, as you probably know, people can change in different ways.

This can cause problems, so it’s especially important to work to be on the same page with the person you’re dating and to also try new things together.

Travel together.

Get your first jobs together.

Live together after a couple years of dating.

These types of events will show you who a person really is and how they respond to stress and what life has to throw at everyone.

Obviously, this tip doesn’t really matter for someone you just started dating.

However, I think it’s important to remember that your 20s is an insane decade so accept that things might end up a whole lot different than you ever expected.

3. Don’t Be Afraid To Date Multiple People

I never understand why some people look down on going on multiple dates with multiple people at the same time.

This is the dating equivalent to getting more shots on net or hooks in the water (or whatever manly analogy you want to use).

I’ve had friends who have gone on one date and were basically like “well, I guess I’ll date this one then!” and then proceed to date some wretched woman for the next year before breaking up, inevitably.

Be choosey, take time, and don’t be afraid to really scout your scene. With dating apps, this is especially easy these days, and it can also be fun!

You can also try to manifest a breakup if the person you’re eyeing is taken…I’m kidding…kind of! 😛

4. Don’t Blow Your Budget

Another massive tip for dating in your 20s as a guy is to not blow your budget when dating.

In my opinion, men should pay for the first date…and most dates, in fact (call it old fashion, but I believe in courtship).

However, this doesn’t mean balling out on fancy dinners every week and destroying your finances.

Personally, I think coffee makes for a great, affordable first-date that’s pretty appealing to normal people.


I also like going for drinks. You can find somewhere with reasonably-priced food or just go around 8:00pm or something so you eat dinner at home.

You can still go to nice places, but factor it into your monthly budget first!

5. Know What You Want

This is another important tip for dudes dating in their 20s that I don’t think we talk about enough as men.

I mean, what do guys talk about when we sit around and talk about what we like in women we started seeing recently?

If you’re with “the boys,” it’ll usually be about something physical or some sort of cool hobby/interest you both have in common.

When’s the last time you stopped to think about other things?

Like…I don’t know, personality traits? Life goals? Family values?

It’s honestly weird, but I know my friends and I don’t really talk about this sort of stuff.

Or, when we do, it’s all surface level…”she isn’t crazy, so I like her!”

I think the biggest lesson I’ve learned since dating in my 20s as a man has been to try and develop a better understanding of what’s most important to me.

I still don’t know, but I have a better understanding than I used to. Ultimately, this helps!

Final Thoughts

Well, there you have it: a jumble of thoughts and tips about dating in your 20s for guys.

Like I said, there’s no right answer for how or when you should date.

However, I think that it’s a good idea to take a step back sometime and to think about what you really want.

Your 20s are an insane time, but that’s largely a good thing.

As long as you focus on yourself, stay healthy, grow your career, and spend time doing what makes you happy, you really can’t go wrong.

The rest comes with time… or so I’ve been told!

Anyway, I’ll catch you guys in the next one!

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