12 Red Flags When Dating an Older Man

I’ll never forget hearing those words: “I thought I could date an older man but something was wrong.”

She looked desperate and at a complete loss as to whether her feelings made sense. But as I got to know her better, she realized dating older guys is amazing. However, there are unique struggles older women face when dating older men.

They can bring confidence, emotional maturity, and experience, but things can get ugly if you don’t know what to look for.

12 red flags when dating an older man

1. Playing Games When He Should Know Better

There are guys that date young women with no intention of getting serious.

Signs include:

Avoiding talk of commitment or the future.
Making empty promises without follow-through.
Wanting to “take things slow” FOREVER.
Not wanting to meet your friends or family.
Preferring things to stay convenient for HIM.

If he dodges conversation around commitment, it’s time to wave goodbye.

2. Trying to Control You or the Relationship

Being experienced doesn’t give him permission to manipulate you.

Some older men feel confident enough (through money, age, experience) to think they can control you.

Look out for:

Making decisions for you.
Criticizing how you spend your money, where you work, or who you spend time with.
Isolating you from family or friends.
Monitoring your every move or social media accounts.
Ignoring your feelings when you voice them.

If he cares about you, he will never try to control you.

3. Constant Comparison to Other (Younger) Women

Yes, some older men love to talk about their younger girlfriends from the past.

This includes:

Talking about ex-girlfriends often.
Comparing you to how skinny/sociable/rich they were.
Saying everything was better when THEY were young.
Teasing you about your lack of experience.
Using their younger girlfriends as ammunition for criticism.

Constant comparison to his younger self or past partners is never okay.

4. Flirting With Other People ALL THE TIME

There’s nothing wrong with being charming or giving women attention.

If he feels the need to flirt INSANELY with waitresses, coworkers, etc., all the time, it’s a problem.

Red flags include:

Giving other women tons of compliments when you’re together.
Making inappropriate comments about other women to you.
Stringing other women along with no intention of keeping things casual.
Constantly checking other women out when you’re out in public.
Making light of your feelings when you confront him.

Flirting with other people isn’t always a dealbreaker, but if he constantly disregards your feelings, it is.

5. Secretive About Personal Life Details

Yes, your older man will most likely have a career, apartment, family already.

He should have no problem being open and transparent with you about the following:

WARNING:

Finances or monetary obligations.
Family life or previous relationship details.
Career, where he lives, or who he spends time with.
Health or habits if you ask about them.
Answering your questions or becoming defensive.

This one can be tricky, but if he withholds information consistently, take note.

6. He Is Emotionally Unavailable

Some men aren’t great at expressing their feelings. But older men are typically the complete opposite.

Here are some signs he may be emotionally unavailable:

He never talks about his feelings.
Avoids deep or meaningful conversations.
Cancels date-night to spend more time at work.
Shuts down when you want to discuss something serious.
Is unable to show you affection.

You deserve a man who will give you all of his emotions.

7. Always Being Negative or Critical

It’s one thing to jokingly point out your flaws every now and then.

It’s another to ALWAYS find something wrong with you.

Examples of constant criticism:

Pointing out both your major flaws and small flaws.
Laughing at your opinions or ideas.
Making jokes about how dumb you are on a REGULAR basis.
Comparing you to other people in a negative way.
Saying you lead an unhealthy lifestyle.

Constant negativity breeds low self-esteem. Don’t allow him to tear you down.

8. Shows Signs of Addiction or Bad Habits

Don’t let his age fool you. Older men can have some serious addictions.

Whether it be alcohol, drugs, cigarettes, gambling, or negative coping habits (angry outbursts, avoidance), take note if he:

Does any of the following:

Drinks or smokes excessively on a daily basis.
Throws money away at casinos or betting games.
Does drugs or turns to substances instead of you.
Uses unhealthy coping mechanisms to deal with stress.
Gets defensive or denies these habits when you bring it up.

These habits only get worse with age, NOT better. Nip them in the bud.

9. Hiding You From His Social Circle

He should WANT to introduce you to all of his friends and family.

If he makes excuses not to invite you places or meets you secretly, he may be:

Avoiding you from:

Going on group dates with his friends.
Keeping your relationship a secret from family/friends.
Criticizing your friends without reason.
Preferring to spend all of his time alone with you.
Diminishing your feelings when you tell him social interaction is important to you.

Introducing you to his world shows he’s serious about you.

10. Obsessed With Youth and Physical Appearance

Some guys will pay extra attention to your body and physical attractiveness.

If he constantly:

Compliments other girls on how skinny/massage/beautiful they are.
Puts pressure on you to look a certain way.
Prefers sex over emotional intimacy.
Compares you to younger girls all the time.
Judges you based on your appearance.

At the end of the day, you should be more than skin deep to him.

11. Has a Track Record of Toxic Relationships

Cheaters, players, guys who curse women out and call them crazy: they all have one thing in common.

If he constantly:

Talks about how his ex cheated on him.
Blames his exes for every mistake that happened in the relationship.
Has short-term relationships that never last and learns no lessons.
Struggles to maintain long-term relationships.
Avoids taking responsibility for breakups in the past.

There’s a difference between growing from your mistakes and repeating them.

12. Is Inconsistent With His Words and Actions

Trust your gut if he says one thing but does another.

Examples of inconsistency:

Changes his communication patterns suddenly (hot and cold).
Gives you mixed signals about how he feels.
Is unpredictable when it comes to spending time with you.
Cancels plans with you last minute, frequently.
Says he wants a serious relationship but acts otherwise.

Remember: actions speak louder than words.

Final Thoughts

Dating an older man can be a great experience. But when you know these red flags when dating an older man, you’ll know how to spot the bad ones.

Look out for men that try to control you, withhold information, avoid commitment, play games, or fall into these patterns consistently.

Don’t ignore your instincts – you deserve the best!

FAQ

Q1: Are older men more likely to have these red flags?

A1: No. Many older men are wonderfully mature and responsible. However, these are red flags to look out for if they occur.

Q2: How do I know if it’s a red flag or a problem that can be talked about?

A2: Pay attention to patterns. If something happens once and he reacts accordingly, it’s probably not a red flag. But if you notice a behavior pattern, that’s a red flag.

Q3: Should I talk to my partner if I confront him about a red flag?

A3: Of course! Always communicate your feelings in a clear way. If he cares about you, he will never consciously repeat the same behavior after you’ve talked.

Q4: Can you avoid red flags altogether?

A4: Some of these are deal breakers (#2, #4, and #9 for example). However, others like #1 and #7 can be improved with communication.

Q5: How do I emotionally protect myself when dating older men?

A5: Set boundaries and communicate. Everything else will fall into place.

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