Dating is never easy, and dating an older guy comes with its own challenges and things you’ll need to be prepared for.
You should always be on the lookout for any red flags in a relationship, and more so take notice and do something about them.
If you’re interested in or already dating a guy who is 5, 10, or maybe even 20 years older, it’s going to be very different from dating a guy the same age as you.
Here are 20 red flags when dating an older man to look out for:
20 Red Flags When Dating an Older Man
1. He Is Stuck in His Ways
Sayings like ‘you can’t teach an old dog new tricks’ are not just cliches. A lot of the time older guys will be stuck in their ways and set in their ways.
This can be frustrating, because you may want him to try new things or do things differently, but it’s likely he’s in a place in his life where he knows what he likes.
This is a huge red flag though, it means you’re going to have a battle on your hands going forward if there are things you want to do that he doesn’t.
2. He’s Not Over His Ex
This is a classic red flag in any new relationship, but an older guy has likely been through more, longer relationships, so it’s something to take seriously.
If he’s still talking about his ex, or if she’s still a big part of his life, then there is a chance he’s not over her.
That’s a situation you don’t want to get involved in and a warning sign that you need to back off till he has it sorted.
3. He Has Kids
I’m not suggesting kids should be a dealbreaker, but it’s something to take into account when dating an older guy.
Kids can potentially present a few problems that you might not see or think of at first, such as:
- He’ll be busy at the times you want to see him like weekends;
- His kids may not like or accept you;
- He probably won’t want kids with you in the future;
You need to think long and hard about how him having kids is going to affect you and think with your head and not just your heart.
4. He Tries Controlling You
A lot of times older guys will want to take the lead and be in control, because that’s how they’re used to things being.
However, this can quickly turn into him trying to control you and your life.
He may want to know where you are all the time, what you’re doing, and who you’re with.
This is not acceptable and is a huge red flag.
5. You Feel Like You’re Being Gaslit
This is a term you might not have heard before, but it’s important to be aware of.
Gaslighting is when someone tries to make you question your reality, memory, and perception.
It’s a form of manipulation and is often used as a way to control someone.
If a guy tries to pull this with you I recommend you run a mile
6. You Don’t Have Many Shared Interests
When you fall in love with someone and there is a huge age gap, you don’t often have a lot of stuff in common.
In the short term, this is fine and you’ll get by on the emotions and feelings you have for one another.
But it’s a red flag to be aware of as over time you’ll likely grow apart unless you make a concerted effort to find things to do together and have shared interests.
7. You Have Different Life Goals
It’s normal to have different life goals when you fall for a guy who is much older than you are as you’re in different stages of life!
However, it can be a difficult thing to overcome and something you need to think about.
If your long-term or life goals don’t align there is going to come a time when one of you is going to have to make a sacrifice, and that’s not always easy or possible.
8. Your Friends Are Warning You About Him
I think we’ve all been guilty of not listening to our friends when they try to warn us about someone we’re dating.
But sometimes, they can see things that we can’t and their warnings should be heeded.
If your friends are trying to tell you something about the older guy you’re dating, listen to them!
9. He Still Sees His Ex
It’s a bad sign if an older guy you’re dating is still seeing his ex when he has no reason to outside of them being friends with them.
It shows he’s not completely over the relationship and still has feelings for her to some extent.
I’m not saying he should cut her off, not at all. But he also needs to take your feelings into consideration and not put you in an awkward position.
10. He’s Depressed or Down
Older guys are more likely to be depressed as they may be coming out of a long-term relationship or marriage and lost a lot.
This isn’t always the case, but it’s something to be aware of.
If he’s down or depressed all the time it can be a real drag and you may find yourself being his therapist rather than his girlfriend.
11. He’s Bitter About Love
Older guys who have been hurt in the past may be bitter about love and women in general.
This can make them act out in strange ways or say hurtful things.
If he comes across like this, even though I’m sure he’s sweet with you, this is a red flag to take notice of.
12. He Says He Loves You Too Soon
This one is a huge red flag and something you should run away from as fast as you can.
Older guys who say they love you too soon are often just trying to manipulate you and control you.
Sure, it’s nice to hear those words, but only when someone really means it and truly values you for who you are.
13. He Wants to Get Married Soon
Similar to saying ‘I love you’ too soon, wanting to get married too soon is also a red flag that should set alarm bells off.
Older guys may want to get married quickly as they feel time is running out, but that’s not a good reason to rush into things.
14. He Compares You to His Ex
Comparing you to his ex is a huge no-no and something you should never put up with.
It’s disrespectful and shows that he’s still thinking about her.
Rather than comparing you, he should be focusing on the present and making sure you feel special and loved.
15. He Doesn’t Try to Get to Know Your Friends
If an older guy you’re dating doesn’t try to get to know your friends, it’s a red flag.
He should be interested in the people you care about and want to make an effort to get to know them.
This is normal for older guys as they may feel like they have nothing in common with your friends or that they’ll judge him.
16. He Won’t Make an Effort with Your Family
A step up from friends is family, if an older guy doesn’t want to get to know your family you should be very wary of them.
You don’t need approval, but I’m sure you’d like it if your family liked the older guy you’re dating.
I can understand a little nerves as families can be difficult, but he should at least try.
17. He Won’t Introduce You to His Friends and Family
If he’s not ready to introduce you to his friends and family, it’s a red flag.
This could be for a number of reasons, but usually, it’s because he’s not that into you or he’s hiding something.
You should certainly bring this up with him, if it’s not a big deal he’ll come up with a solution pretty quickly.
18. He’s Still Married but Says He’s Separated
This might be one of the biggest red flags you’ll come across when dating an older guy.
If he’s still married but says he’s separated, there’s a good chance he’s lying to you – or at the very least isn’t fully checked out of his last relationship.
There could be a number of reasons why he’s doing this, but whatever the reason you shouldn’t be with someone who isn’t single (yet).
19. He Isn’t Letting You Get Close Emotionally
If you’re dating an older guy and he’s not letting you get close emotionally, it’s a red flag.
He may be doing this for a number of reasons such as not being over his ex, not wanting to get hurt again, or simply because he’s not that into you.
Whatever his reason, it’s something you shouldn’t ignore.
You deserve to be with a guy who is willing to open up emotionally and offer his best self to you.
Related – 15 signs you’re being lead on!
20. He Flirts with Other Women in Front of You
If an older guy is newly single after a long relationship he may not be used to flirting or he may think it’s harmless fun.
However, if he’s doing this in front of you it’s a red flag.
It shows that he doesn’t respect you if he is happy to flirt with other women right in front of your face.
He might be enjoying his post-marriage life a little bit too much!
Phil lives in England, UK, and has around 20 years experience as a professional life, career and executive coach. He started this blog to help others find and define their own self development journey. Blogging about a wide range of topics to help facilitate a better future.