Dating Advice for a Man in His 20s 30s 40s

Dating Advice for a Man in His 20s 30s 40s

Dating advice for a man in his 20s 30s 40s is different than for a man in his 50s and beyond because younger men are in a different stage of life.

Stages of Life

Dating Advice for a Man in His 20s

When you’re in your 20s, you’re figuring out your future and who you are in the world.

At the same time, you’ve got the most testosterone you’ll ever have coursing through your system, so you’re horny AF.

Biologically, your body wants to spread the love, or at least your seed, to as many females as possible.

But you should use your 20s to focus on your career path and discovering your life mission.

Settling down shouldn’t be your highest priority.

That’s not to say you shouldn’t date!

Your 20s are about learning and exploration—

  • What work works for you.
  • And what women work for you… as in, testing out the ice cream flavours.

This doesn’t mean you need to have a bunch of girlfriends or sleep around a lot.

There’s a terrible mistruth young men believe about only being a man if he’s a stud and has been with a lot of girls.

This is toxic masculinity and this one you put on yourselves, I’m afraid, by assuming macho = masculine. #wrong

It’s ok to not want to sleep around!

And if you do want to date one or five girls, remember women don’t expect you to have wads of cash at this stage of your life.

But they do expect you to be working toward financial independence (via study or work).

Even if you choose to abstain from dating to focus exclusively on study or career, get to know enough women to figure out the traits you like and don’t like in them.

My dating advice for a man in his 20s is to focus on working toward a career while learning to understand women (by firsthand experience) so you’ll be prepared for your 30s.

Dating Advice for a Man in His 30s

If you’re a man in your late 20s or early 30s and know you want a family, this is when to start thinking about settling down (without settling) with the right woman!

The good news is you have time to filter filter filter for the good ones because your swimmers will be active for many years to come!

Don’t trick yourself into thinking you’re running out of time and try to make it work with someone who isn’t the right one.

Building Your Kingdom

This stage in your 30s is about building your career kingdom and starting to pay off student loans, if applicable, or save for something meaningful like a better car or downpayment for a home.

If in your 20s you sampled enough relationships with women, even if simply friendships, you should have a good idea of the traits you want and don’t want in a woman.

And though your sex drive is still relatively high, you may be ready to give it all to one good (deserving) woman.

Key words: Good woman.

If you decide to marry, divorce isn’t fun, emotionally or financially!

Remember: Love and attraction are not enough. Be choosy!

WakeUP2Luv provides a step-by-step process for how to do this, regardless of whether or not you’ve even had a girlfriend.

If you don’t want a family or are unsure, then carry on as before, Sir. Keep your focus on building your career kingdom.

Dating Advice for a Man in His 40s

A man in his 40s has a different mission depending if he’s in a committed relationship and/or has a family or if he’s continuing down the bachelor path.

If he’s got a family, his mission is to ensure his family is fed and happy while maintaining his own needs.

A man with a girlfriend/wife without children needs to maintain that relationship and do his part to keep his woman happy.

If it’s a healthy relationship, she will want to do the same for him, including honouring his need for physical intimacy and variety within the relationship.

To keep a relationship healthy, choose wisely in the beginning (#WakeUP2Luv), and, like your favourite dirt bike, service her regularly.

No, I don’t mean sex, though that’s part of it. I mean checking in and never, I mean NEVERRR, taking her for granted.

Watch: How to Keep a Woman Happy.

Side note: If you’re having some trouble with ED, you may have early onset low testosterone. More on that here.

40s Forever Bachelors

My dating advice for a man in his 20s is only slightly different than it is for a man in his 40s who’s single and has never been married or been financially shafted in a divorce.

Men in their 40s are either living la vida loca as a bachelor or divorced and licking their wounds.

Whether you’re playing the field or starting from scratch after a nasty divorce, make sure you’ve got your career and finances in order, because no good woman is going to want a man who’s broke with no job.

If you’re divorced, there’s a good chance you feel or felt bitter about the separation because divorce is not fun, emotionally or financially, especially for men.

Do your best to not carry bitterness into your dating life or you’ll turn off the good ones and only attract bad ones, if any.

Watch: Damaged Women Do “These” Things.

Avoid choosing poorly (again) by going through the process in WakeUP2Luv on how to train your brain to spot the red flags you personally are most likely to miss seeing.

If you’re wondering about whether or not to date a single mom, watch: Should You Date a Single Mom?

When you get to your 50s, hopefully you’ve established your kingdom and rule it with a deserving queen by your side.

Bonus Tips for a Man in his 20s 30s 40s

This advice applies to all age ranges, but more so in the younger age ranges.

1. Don’t assume she’ll change!

Never go for potential hoping that with your love and devotion she’ll magically become the woman you want her to be.

You’ve got to be okay with accepting her “as is where is” with her warts and flaws and all in case she can’t (or won’t) change.

Change is difficult even when we want to change, but changing for someone else is even more challenging.

Yep, I tell women the same thing. They are even more guilty of trying to change a man!

2. Assume she will change!

Wait, what?

Although she may not change in the ways you want her to, she will change over time, just as you will.

Her ideas, goals, preferences, opinions on things will evolve over time.

These changes may stay in alignment with your ideas, goals and opinions or they may not.

It is critical your fundamental values align before committing to a long term relationship.

When your values align, there’s realistic hope of compromise, adjustment and a happily ever after.

If they don’t align, you’re doomed for pain and suffering.

So honour whatever stage you’re in and know when you’re ready, if you’ve done the prep, you can find, attract and keep a keeper.

Watch: She’s a Keeper IF…

Oh, and get my WakeUP2Luv program! Do the work, change your life.

xo AJ

If you want to weed out the girls that’ll give you trouble and only wake up to fun, sexy, worthy cuddle buddies, get  WakeUP2Luv and do the homework!


Single Moms:
Red flags:
Damaged & Toxic Women:

Get Your Testosterone Checked!



About the Author Anna Jorgensen

Vancouver dating coach for men who love women! ❤️ (Not PC and not a feminist.)

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