3 “Older Guy” Mistakes Men Make with Women

DatingAttraction > Older Guy Mistakes
by Bobby Rio • Updated: August 30, 2022

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older guy dating mistakes

3 Reasons “Older Guys” Blow it With Younger Women

So recently I’ve had the itch to take on some more personal coaching clients

To be honest, I don’t do it for the money, as the time/value doesn’t make much sense for me anymore…

I do it because it gives me a chance to really see the different areas where guys are still struggling (even guys who have learned a lot)…

So, a handful of my clients are men past the age of 40…

I’ve recognized a few common mistakes older guys make.

Now, first off, if you think “I’m not over 40 this doesn’t apply to me” … it does.

Because the fact of the matter unless you’re 18 years old… there are girls out there that consider you the “older guy.”

So let’s examine these mistakes

“Older Guy” Mistake #1: Lowering yourself to her level to fit in with her age group.

Too often guys feel the need to act younger around a younger girl.

But when you do this you come across as “supplicating” yourself and trying hard.

It is way better to embrace your maturity than to hide it.

Would George Clooney try to act/dress/talk like a 25 year old when hanging out with a younger woman?


He would use his age as an advantage.

And more than likely she would be trying to raise herself to fit in with his age group.

“Older Guy” Mistake #2: Bringing your age to her attention with self deprecating jokes

Another mistake I see older guys making is continually making self deprecating remarks about their age.

They joke around like “Im not young anymore” Or “Back in my day”

Guys usually do this because they are uncomfortable with the age difference and they try to ease the tension they feel with jokes.

But in the end, this just lets the girl know you’re uncomfortable, and eventually it’s going to make her uncomfortable.

It also continually brings the age difference to her attention, preventing her for just enjoying your company without thinking about whether you’re “too old” for her.

“Older Guy” Mistake #3: Failing Girls (age related) Tests

So a lot of times girls will test older guys with comments like:

“Why are you still single at 40?”


“You’re too old to be here”

It is a TRAP.

Just ignore the comments and continue along with the conversation.

The worst thing you can do is start explaining yourself to her “Well, I haven’t met the right person… I’ve been focused on work.”

Just ignore the trap. No good will come from it.

And the truth is, when a woman is attracted to you age means NOTHING.

In fact, a lot of times it is EASIER as an older man to date a younger woman.

See Also:

#1 Dating Tip for “Older Guys