Dating An Older Man In Your 20s – 15 Things To Seriously Think About

Dating An Older Man In Your 20s
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As a young woman seeking stability and maturity in relationships, you may sometimes be attracted to men significantly older than you. You might even discover that older men offer comfort and security like no one else. Or perhaps you’re just tired of the mind games guys your age play on the dating scene. This may push you to start dating an older man in your 20s.

Many women around us probably notice the older man attraction signs during college or mid-20s. Unfortunately, not all of them happen to gather the guts to approach the desired man. Typically, a young woman getting sexually attracted to an older man is quite natural and it’s her and only her decision to pursue this or not. But, there are still certain stigmas prevailing in our society regarding older man younger woman relationship issues.

While such a relationship has its plus points, many factors need to be taken into consideration to make a sound choice. Love should not be barred by age but a relationship with a big age gap does come with its own unique challenges. On the flip side, when compatibility, attraction, and desire all fit perfectly, then age becomes a mere number.

There is no rulebook in the world that can dictate how and in which way to love another person. Dating an older man in your 20s can be a bountiful experience provided that you are ready for it. With the right tips for dating an older man, you can make it even more rewarding.  

Dating An Older Man In Your 20s – 15 Things To Consider 

The stability and strength that an older man brings to a relationship are unquestionable. If you look at dating an older man psychology closely, you’ll realize that it is one of the driving forces behind their appeal among young women. Having experienced so much, they can see life in a way that you are yet to understand. You can not only learn from his maturity but an older man can also guide you through a relationship with ease.

Being sexually attracted to older men is one thing. That might be a kinky thing or a purely physical desire. But how do you know if it is real love? It’s important to differentiate between the two so that you know what to expect when dating an older man. It’s no wonder your worlds will be poles apart, with divergent habits, goals, passion, acquaintances, and pace of life. Unless some of these factors align, the relationship won’t be worth your while.

I remember, one of my colleagues once told me, “My experience dating an older man went south right when I realized I was getting way too attached to him. But he was only sowing his wild oats, playing the field.” It is possible that a man in his 40s or 50s doesn’t want to start a fresh new chapter. Your partner showing signs of a commitment-phobe can drain the relationship. Especially if you are looking for a promising future with him.

An older man younger woman relationship is not unheard of. May-December pairings have not only dominated the world of romantic fiction and the silver screen but are abundant in the real world too. Falling in love despite – or because of – the difference in age is very much possible. However, there are some things that you should be mindful of. If you have been dating an older man in your 20s, here are 15 things worth considering to understand what kind of future you can build together: 

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1. Does he have children?

This is the foremost concern when it comes to dating somebody far older than you. If you are in your 20s and dating a man 15 years older, there is a good chance he will have children. Dating someone also means accepting them and every aspect of their life.

If you are dating a single dad, you have to be prepared to accept that his children are part of the package. Well, you may not need to have a relationship with them right off the bat but they will be a strong determining factor in your dating life. Whether your man can make it to that date or go on that weekend trip with you will always depend on whether or not his children are well taken care of.

It is something you have to welcome with open arms into your life. His children may eventually become a part of your life too in some ways. You do not necessarily need to approach this set-up like a step-parent. However, you will need to have some extra space in your life for them. 

2. Sexual compatibility

sexual compatibility when dating an older man
You must consider your and your partner’s sexual needs and preferences

“I have a crush on a man older than me” – this realization may wash you over with a sense of excitement and anticipation. It happens often when we meet a ruggedly handsome man at the dentist’s office or a dreamy guy with salt and pepper hair while running in the park.

We feel ya! Once or twice, almost every young woman has felt sexually attracted to an older man. However, before you go with the flow of these warm, fuzzy feelings, pause for a moment’s reality check. Sex drives vary tremendously across ages. What may seem sexy and exciting to you now might be redundant and overrated to your boyfriend. Not only is an older man more mature emotionally, but he is also far more experienced than you sexually. 

Having tried and tested many things in bed, if you are lucky, you might get to explore new kinks or unheard positions that he may have learned over the years. On the other hand, due to his age, he might say no to sex and may not indulge in intimacy the way you would expect him to. 

Related Reading: Sexual Compatibility – Meaning, Importance And Signs

3. Do you notice generational gaps?

When a younger woman likes an older man, they can’t avoid the big generational gap between them. Girls in their 20s are often labeled as seeking sugar daddies if they’re in a relationship with an older man. In fact, I have seen mean comments on social media where people intentionally confuse their SOs for their fathers.

“If I have learned anything from my experience dating an older man, it is that societal scrutiny is not the only issue that arises from this generational gap. The cultural differences can be very, very evident in relationships with large age gaps. This can even cause dating anxiety. If you are dating a man 10 years older, know that he will not look at things with the same lens as you. His prime years were in a different time and he is still attuned to them,” said Linda, a 22-year-old post-graduate student at Yale.

He will most certainly have a more aged viewpoint about various socio-political issues. And it can create some trouble if he is not flexible in his opinions or open to accepting yours. For example, he may not share the same interest in posting away on Instagram as you do or understand your book reading choices. He might be an avid reader of the classics and not understand your taste in reading feminist narrations by Black women. 

4. You may have different future priorities 

As a young woman, your future is still in your hands, waiting to be mapped out. But dating an older man in your 20s can bring a whole different set of priorities into your relationship equation. The things that matter to your boyfriend can be markedly different from the ones that you care about, and this can become a breeding ground for relationship arguments.

As a man who has lived and worked enough already, he may want to recline a little and settle down for good. It is fair for him to find a long-term residence or indulge more in hobbies rather than being brazenly career-driven. You may be moving from one opportunity to another and he might be happy just where he is. 

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5. He may patronize you 

When dating with an age gap, his sense of superiority might tower over you in terms of decision-making. It may not be done intentionally to make you feel smaller but can come naturally owing to his advanced maturity. From the tiniest things like which Broadway show is better to which car dealership is more reliable, he might try to make all the decisions for you.

Note that he may not do this to humiliate you but is only looking out for you and wants you to avoid making the mistakes he did. One of the tips for dating an older man is to not normalize these ‘I told you so’ moments in your relationship. Talk to him, without accusations or putting him in a spot, about the importance of partners being equals, the difference in their age notwithstanding.

6. Understanding the finances 

Yes, money issues can ruin your relationship. When you and your boyfriend are at vastly different places in your life, your bank balances and credit card debts may not align. When you’re saving up to pay for your student loans, he might want to finally throw his savings on extravagant vacations. This is an overlooked aspect of dating an older man in your 20s. With different priorities, you are bound to want to spend differently.

This is hardly a deal-breaker but it might be good to discuss how you want to spend your money together as a couple. If he wants to lavish his money on enhancing your experiences as a couple, and you’re okay with it, then it’s all very well. But if that’s something that’s unacceptable to either of you, an honest discussion about expenses is warranted early on in your dating journey.

Related Reading: Money And Marriage Tips: 12 Ways To Sort Out Finances In A Marriage And Grow Rich

7. Your friend circle might not be the same 

When you are dating an older man in your 20s, do not be surprised if he does not show up at your girls’ night out to charm away your friends. When you go to his poker nights with his friends where the men are all discussing their wives and kids, it might not be so easy to weave yourself into his social circle. 

You will always have different types of friends. You may be able to hit off with your mixed group of friends once or twice, but it’s unlikely to evolve into a long-term group friendship. To prevent this from becoming a point of contention in your relationship, you must understand dating older men psychology and he, yours. Accept that you’re in different places in your lives, and some parts just may not converge.  

8. Getting your parents on board 

This is a big battle in itself. There is still a stigma attached to being with someone much older than you. “If I have learned anything from my experience dating an older man, it says this whole concept hits hard on our old-school parents. Even if your parents are open to it, they may raise a variety of questions and concerns that you cannot simply dodge,” Linda adds, elaborating on the challenges she faced dating an older man.

No wonder they will be concerned more about your future as a couple. When you date a man with 30 years of age gap, what’s the certainty he will be there for you for a long time? Plus, there is the most recurring question – What will we say to our friends and family?

Moreover, winning over your boyfriend’s mom will be harder than you think. It can be even more awkward when your boyfriend is just as old as your dad. While they may get along while playing a round of golf, your father may not consider someone his age exactly suitable for you. Time to cross your fingers! Take your time to be sure about your partner and your future together before you spring this relationship with a big age gap on your family and his.

9. Know his true intentions 

While love can exist across the spectrum of age, you must still be careful about what you are getting yourself into. In certain instances you may wonder, why do older guys like me? He might be just using you as a trophy girlfriend. A lot of older men prefer to date younger women to elevate their social status.

It makes them appear more desirable and they enjoy the energy that young women bring to life. Be careful of your boyfriend’s intentions before jumping into something serious with him. He may leave you down the line when he finds something shinier. Among the valuable tips for dating an older man is that you must take the time to look into his past relationships and dating patterns before getting too emotionally invested.

dating older men psychology
Discuss with him and understand what he truly wants from this

10. He might have way too much time for you 

Sometimes when a younger woman likes an older man, the romance between them starts on a high note. Mainly because this woman reintroduces him to the fine colors of youth and carefree life. Although that might come back like a boomerang if her partner goes overboard with the relationship. If he is retired, he may be looking to spend his life with ease and spend his golden days at his whims.

In that case, you cannot rule out the possibility that he might be falling in love too fast. Also, if you both find an instant connection, you may quickly become the center of his world. For him, you might be the top priority but since you are still in the phase of building your life, you might not always have too much time to give to him. 

While every woman would love to have a partner for whom she is the top priority, it can meddle with how much time you want to spend together or apart. Make sure you discuss your life goals and plans with the older man you’re dating so that you’re both on the same page about how much of yourselves to give to the relationship 

11. Watch out for your emotionality 

As a young woman, you are allowed a few mistakes, misunderstandings, and emotional screw-ups. A few tantrums, jealousy, or insecurity all come with relationships. Just because you are with an older man does not mean you can dispose of who you are naturally meant to be. As my dear friend, Sophie, says, “My experience dating an older man suggests that to keep up with him and constantly learn, you have to be more alert about your responses.”

He may not entertain petty mind games and could be harsh on you when you act immature. Even when dating a man 10 years older than you, you may find that you’re both in a different headspace on a lot of things. Emotional maturity is definitely one of them. Once again, the key is to find a middle ground that works for both of you and be willing to make some adjustments.

Related Reading: 12 Signs Of Insecure Women And How To Avoid Them

12. You will communicate differently 

Older men are often into more serious dating and want to take things long-term. Because of this, their communication will be more open and honest. They may also layout all their expectations in front of you without a thought. As a young woman who is still navigating what she wants, your communication may be more elusive, coquettish, and without any actual serious inclinations. This can make it challenging to build an interdependent relationship.

On the plus side, you will never have to worry about being ghosted, having to deal with who-texts-first mind games, or evading the uncomfortable “where is this going” conversation. He will be ready to give you something real and meaningful, and as long as you don’t dread the idea of making a strong commitment so early on in life, it can work out well for you.

13. He will not be jealous of your exes but you will be of his 

As a successful man who has lived and learned, he will not be petty enough to be jealous of all the younger men who have been in your life before. There is nothing for him to be intimidated by men who are still trying to make something of themselves. 

Your boyfriend might, however, have ex-wives or serious past relationships that can intimidate you and make you act like an unhealthily jealous partner. Around these women who have completely understood the ways of the world, you might feel like a newbie in comparison. However, do not compare yourself to someone who is in completely different shoes. Your pace and path will always be unique. 

14. Your expectations will be different 

I am sure you remember the epic love story of Monica and Richard from Friends. They went across all odds, convincing her parents and keeping the relationship very much alive. But in the end, a huge difference in their individual expectations of the relationship ruined its essence. As an old man in his 60s, Richard didn’t want to have kids, which was a deal-breaker for Monica.

You should consider similar older man younger woman relationship issues before getting into one. Even when it comes to sharing responsibilities, you both may be on different tangents in terms of what you expect from the other person. At a time like this, it is important to try to have realistic expectations from one another.

15. He might judge you less 

If you’re wondering what dating an older man in your 20s can be like, know that it can be a refreshing experience in many ways. You shouldn’t fight it when you begin to notice older man attraction signs in yourself. Embrace your emotion and feelings and convey them to the man of your dreams.

Older men have already been through the confusing stages of life and have made the same mistakes that you are making. While they might want to guide or reprimand you at times, they will never judge you for anything! They are aware of what every stage of life brings out in a person and might share a laugh or two reminiscing their own silliness.  

Being in an age-gap relationship has its pros and cons. Just like any other couple, you two will face challenges that are unique to your equation. We hope that now you are well aware of what to expect when dating an older man. You know the obstacles coming in your way – from family and so-called societal judgment, as well as in your relationship itself. With these tips for dating an older man, you’d be better poised to navigate these more skillfully.


1. What attracts a younger woman to an older man?

A younger woman often appreciates the maturity, resilience and emotional maturity that older men bring to a relationship. 

2. Do age gap relationships last?

Any relationship can last as long as both partners are committed and dedicated to it.

3. How much older is too much older to date?

People often follow this equation. Take your age, subtract 7 by it and then double that number. That can be your upper limit for dating. However, this is just a guide and you can pick your own limit too.  

4. Do younger women older men relationships work?

If there’s love and compatibility between a couple and the two are in sync, it can certainly work.

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