How Men Should Date In Their Late 20s

February 8, 2023
How Men Should Date In Their Late 20s
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Once a man hits his late 20s, the pressure sets in. He’s either going to stay focused on becoming financially stable or take dating a lot more seriously.

But what is the right course for a man at this important juncture in his life? Should he get serious, tie the knot, and start a family with twins on the way? Or should he prioritize himself before entering a committed relationship with a woman?

I’ll answer all of that here in this blog post.

A Man's 20s Should Be About His Money

If you’re absolutely broke and have nothing going on in your life in your late 20s (26-29), you have to get your money right.

Forget about love or women.

Time is ticking. 30 is around the corner and before you know it, 35 will creep up…all of the sudden you are 40 and still broke AF. What you do in your late 20s absolutely matters.

Time is not on your side. At a minimum, you need some kind of career. Whether it’s a government job, a trade, a job in software development, medicine, or sales, you have to at least be on your way to hitting around $100k minimum.

If you aren’t anywhere close to that at this age, start figuring it out. Now is the time. Do not wait until your 30s.

Finding your passion, mission, purpose, career, or whatever it is you want to term it, will not just work itself out or come to you. You have to dedicate time and effort to achieve long-term stability.

What if you’re not absolutely broke?

If you’re on your way to getting your life in order financially, then it’s fine to start dating more seriously at this point. Maybe you’re about to finish med school, just took the bar exam, or your side hustle is starting to make profit. Now could definitely be a great time to meet the right woman.


More often than not, men regret not having children sooner in life. At 28, you can probably get hitched by 30. And by 35, you can have 1-2 kids.

Most guys get tremendous joy in having kids earlier in life knowing they can have a few more on the way.

Although we live in a time where everyone wants to flex and sleep around, this provides only so much satisfaction. Men get bored.

Guys eventually get more excited seeing this:

happy family

Versus this:

hot chick big lips

With the latter, sure she's hot but you’ll get bored of her if she can’t provide you the former.

You have to ask yourself what will make you most happy. And most of the time, it’s a hot wife you can trust, financial security, and good children. That should be where your mindset is in your late 20s. So how does one date with that goal in mind? Let’s break it down.

Have The Right Dating Pool

Dating apps these days are brutal.

80% of the women profiles say “4 kids, separated, and not looking to play any games. I need my rent paid also. Keep moving if you’re looking for fun.” Others are OnlyFans “models” that try to stir you to their IG profile and turn you into a paying customer.

This is why you need to invest into two things:

  1. Instagram
  2. Better dating sites

Instagram is a good place to meet local women. You want a solid looking profile first. Then you want to message local girls only. I’m not going to get into the ins and outs of Instagram but if you want a guide on how to meet more girls on Instagram, click that link.

Look into more premium dating apps and pay for the subscription fee - Eharmony, Christianmingle, etc. Guys definitely do have luck on these sites. They have better quality women typically compared to the Badoos and POFs of the world. The women tend to be more serious also.

But you still want to step away from the screen.

Be as social as you can.

There’s a lot of single women out there and it’s way easier to land dates with them if you have mutual friends in common. The more people you know, the more women you can meet.

  1. Reconnect with old friends via FB and invite them out
  2. Go out to every event you’re invited to
  3. Become a regular at popular hangout places
  4. Talk to people more often – initiate conversations.

The more you’re involved in the world, the higher the chance you’ll meet someone. So, let’s say you started dating. In case you haven't went out with a girl in a while, this primer on how to master the first date should help you.

But suppose things are going well. What should you be looking for in a girl before deciding if things should get serious?

Mature Women Only

What’s maturity in a woman?

Someone with a high paying job?

There’s plenty of toxic, unhinged, insane women with high paying jobs who are nothing but immature outside of work.

A girl with a good job is nice, but it doesn’t signal maturity.

Maturity is knowing what she wants out of life long-term.

Does she have a good head on her shoulders? Or is she often confused, looking to find herself, and making unsound decisions? That's something you need to determine about her.

She also needs to be over the clubs and partying at this point.

There’s nothing wrong with dating a girl who used to club a lot but you want to make sure she's really past that phase at this point.

Analyze Her Family

Dating seriously is a big deal.

Not only should you be looking at your chemistry together, but her family comes into play also.

If she has a big close family where they have dinner every Sunday, guess what? You’ll be having dinner there every Sunday. If that’s something you have zero interest in, she might not be for you.

What if you love the idea of a big close family yet hers have a serious history of criminal activity, drug addiction, and drama? She might be hot and great but again, you’re not only marrying her, you’re marrying her family.

And what if she involves her parents into everything? Her mom and her are super tight and she knows most of her daughter’s business, including private details of your relationship.

Guess what?

Expect lots of meddling into your private affairs.

Think long-term.

Picture who will be the grandparents of your children. If you’re uncomfortable with her family being your in-laws, then reconsider your relationship with her.

What Are Her Politics Like?

Politics matters long-term.

Even if you’re apolitical and don’t care about anything, if she’s very passionate when it comes to a certain side of politics, be prepared to hear about it often and have her children raised to her point of view.

If you’re political, you obviously want to make sure you and her see eye to eye.

Once the passion dies down between you two, all that’s left is your personality and compatibility. If you both disagree on major issues, this probably isn’t a good match.

The Role of Money

Money has to be a consideration when dating seriously in your late 20s.

Is she in school for a useless degree?

If you want a woman who will make a reasonable income in the future, then this is something to think about.

What if you’re well off and prefer to marry a housewife? You need to confirm she’s down for that lifestyle.

Some women want that executive role where they work late hours and have cocktails with co-workers after. While others will happily play the role of a housewife.

Tip: Keep her spending habits in mind. A housewife can spend a lot of money on her time off. If you’re a baller, then this may not be an issue for you. If you do well but not on the level of baller status, then unreasonable spending can be a damaging quality that you should not overlook.

Social Life

Do you like it when a girl has a bunch of friends?

Or do you prefer someone more introverted?

With a big group of friends comes big comparisons.

Sometimes a girl starts paying attention at how much her friends’ husbands make, where they travel and how they have better handbags than her. All of the sudden the pressure is on you to keep up with her circle.

Not every girl is money hungry. There’s plenty of women out there fine with a more modest lifestyle who just want a good husband and some kids.

But you’ll definitely come across women who have a stronger inclination towards materialism. There’s nothing wrong with that either. Having nice things is amazing. Just be aware what you’re getting yourself into before putting a ring on it, and that you can keep up with the Joneses.


Dating in your late 20s definitely comes with pressure. Marrying the right girl is the most important decision you’ll ever make in life. Never rush the decision.

Attraction is obviously important but so is trust, chemistry, and aligned values. Make sure she checks the most important boxes before taking things to the next level.

Do you need help in knowing how exactly to navigate the dating scene? My dating newsletter can help. You'll get exclusive tips on dating, attracting women, self-improvement, confidence, and style emailed to you multiple times per week.

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Men's Dating Coach

I'm a men's dating coach with over 300,000 social media followers and 25,000+ email subscribers. I’ve coached hundreds of men from all over the world and helped them with dating, relationships, and self-improvement.