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

Dating experience | | , Expert Blogger
Updated On: March 13, 2024
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Have you ever thought about what would compel you to start dating an older man in your 20s? As a young woman seeking stability, comfort, and maturity in relationships, you might get attracted to men significantly older than you. Or perhaps you’re just tired of the mind games guys your own age play on the dating scene.

Many women notice some older man attraction signs during college years or mid-20s. For a woman over 24 years of age, being sexually attracted to older men isn’t supposed to be a big deal. It’s her decision to pursue this attraction or not. However, relationships with older men are not viewed kindly, and for understandable reasons like grooming, sexual exploitation, and misogyny.

Even if you trust this guy and have ensured alignment of values, a relationship with a big age difference comes with its unique challenges. So, if you have inhibitions like “What is it like dating an older man?” and “What are the disadvantages of dating a separated man?”, we are here to guide you through this journey like a pro.

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

The balance and security that a single old man brings to a relationship is 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. Not only are they financially stable, but having experienced so much, they can see life in a way that you are yet to understand. One of the benefits of dating a man 10 years older is that he can guide you through relationship minefields with ease.

Being sexually attracted to older men is one thing. That might be a kink or a purely physical desire. But how do you know if it’s real love? It’s important to differentiate between the two especially if you crave a serious relationship or plan on marrying an older man anytime soon. Your worlds will be poles apart, with divergent habits, goals, passions, acquaintances, and pace of life. Unless some of these factors align, the relationship won’t be worth your while.

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. However, we want to make sure you are in it for all the right reasons and not because of something like overbearing daddy issues. 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.

Related Reading: Sexual Compatibility – Meaning, Importance And Signs

1. Does he have children?

This is the foremost concern when it comes to dating a much older man. If you are in your 20s and dating a man 15 years older, there is a good chance he will have children. To add to your surprise, they might even be of your age group making it more difficult to gel with them. However, being in love also means accepting this person 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. 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. Our tips on dating an older man with kids would be:

  • To begin with, make sure he is into you romantically and not seeking child support after a divorce
  • 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
  • You do not necessarily need to approach this setup like a step-parent. However, you will need to have some extra space in your life for them
  • Not to be pessimistic, but the kids may have a hard time accepting you in their life and treat you with nothing but hostility
  • If you are looking forward to a long-term relationship with this man, be patient and make a genuine effort to bond with his children until they warm up to you
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2. Gauge your sexual compatibility

“Why am I attracted to a man 20 years older than me?” – This state of mind may wash over you with a sense of excitement and anticipation. It happens 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! Almost every woman in her 20s has felt sexually attracted to an older man. In fact, dating an older guy can be a bountiful life experience provided that elements of compatibility, attraction, and desire fit perfectly.

However, before you get carried away with these warm, fuzzy feelings, pause for a moment’s reality check and think of the advantages and disadvantages of sleeping with an older man. On a positive note, 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 positions that he may have learned over the years.

On the other hand, sex drives vary tremendously across ages. What may seem sexy and exciting to you now might be redundant and overrated to your boyfriend. Due to his age, he might say no to sex and may not indulge in intimacy the way you would expect him to and that certainly counts as one of the cons of dating an older man. Or, maybe he would want a ‘lot’ of intimacy. Is your man with you just for sex? Test him on this before you get serious with him.

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 partners 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 generational gap. The cultural differences can be very evident in relationships with large age gaps. This can even cause dating anxiety. In an affair with an older man, you should know that he will not look at things through the same lens as you. His prime years were in a different time and he is still attuned to them,” said Linda, a 25-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. 

Related Reading: 15 Tips For Financial Planning For Newly Married Couples

4. You may have different future priorities 

What does a 70-year-old man want in a relationship? If you really think about it, you both are bound to have very distinct goals for the next five years in terms of relationships and life in general. As the younger one in this equation, your future is still in your hands, waiting to be mapped out. But dating an older man in your 20s can bring along a whole different set of priorities.

What counts as important to your man can be markedly different from what you care about, and this can become a breeding ground for relationship arguments. So, if you are in love with an older man or wondering, “Is 21 too young to be in a serious relationship? How do you know if it’s real love?”, consider these scenarios before getting your hopes too high:

  • As a man who has lived a fulfilling life, he may want to recline a little and settle down for good
  • Given how financially stable he is, 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
  • He may be on board with the idea of a serious relationship but can step back when it comes to marriage or having children. He may not want to start all over again at this age

5. If you’re dating a much older man, he may patronize you 

When dating with an age gap, his sense of superiority might tower over you in terms of decision-making. Call it a downside of dating an older guy if you may. This can be quite triggering especially if you don’t do well being controlled in a relationship. It may not be done intentionally to make you feel smaller or to treat you like his possession.

But at the end of the day, his maturity, manhood, and life experience might urge him to dictate how things are done in an adult way. To him, it’s just good advice. 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. If your dilemma is “I am marrying a man 20 years older than me. Is it a bad thing he treats me like a child? How to act mature in a relationship?”, here’s how you cope:

  • Note that he may not do this to humiliate you but is only looking out for you and wants you to avoid the mistakes he made
  • One of the tips for dating an older man is to not normalize ‘I told you so’ moments in your relationship
  • If you keep questioning yourself with “Why do older guys like me?”, maybe it’s time to reflect on whether you are being too naïve or easy to manipulate
  • Talk to him, without accusations or putting him on a spot, about the importance of partners being equals, the age difference notwithstanding
dating a much older man
One of the drawbacks of dating someone much older is that he might try to patronize you

6. Understanding the finances before you get serious with each other is essential

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 use his savings for extravagant vacations. Money issues can ruin your relationship: This is an overlooked aspect of dating a man 15 years older.

With different priorities, you are bound to want to spend differently. As he is financially stable, his idea of having a good time may wildly vary from yours. Of course, you wouldn’t want to waste thousands of dollars on luxury wine or invest in a country home at 25. We are not saying it’s a bad thing, but it may not match your way of living. This can invite trouble in the long run. Consider these points:

  • 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 or to make you feel special with fancy gifts, and you’re okay with it, then it’s great
  • But if that’s unacceptable to either of you, an honest discussion about expenses is warranted early on in your dating journey

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. Also, 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 should understand yours. Accept that you’re in different places in your lives, and some parts just may not converge.  

Related Reading: How Important Are Common Interests In Relationships?

8. Getting your parents on board is tricky when you are dating with an age gap

This is a big battle in itself. There is stigma attached to being with someone much older than you. “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. So, be sure about your partner and your future together before you spring this relationship with a big age gap on your family and his,” Linda adds, elaborating on the challenges she faced dating an older man.

Your folks will be concerned about your future as a couple. When you date a man with 20 years of age difference, 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 meets your dad and they are both the same age.

Even if your partner and your dad get along during a round of golf, the latter may not consider someone his age suitable for you. Remember Ross in Friends? His meeting with Bruce Willis’ character, the father of his young partner, was the definition of awkward. If your situation is anything like that, it’s time to cross your fingers!

9. Knowing your date’s true intentions is a must regardless of their age

What does a 70-year-old man want in a relationship? It is probably safe to say that he is not looking for a wife when he dates a girl in her 20s. Then what is a man looking for in a relationship? That should be your primary concern while decoding dating older men psychology. It’s true that love can exist across the age spectrum but you must still be careful about what you are getting yourself into.

You may wonder, “Why do older guys like me?” Well, dating a woman half their age might come as a breath of fresh air and they might genuinely treasure your existence in their life. Or they might just be 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 their life. We suggest the following:

  • 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 navigating relationships with older men, one is this: Take your time to look into his past relationships and dating patterns before getting too emotionally invested

10. He might have way too much free time for you 

Sometimes when a younger woman is dating a much 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. This 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 the liberty of spending too much quality time with him. 

While every woman would love to have a partner for whom she is the top priority, one of the disadvantages of sleeping with an older man is that it can meddle with how much time you can devote to one another. Make sure you discuss your life goals and plans with him so that you’re both on the same page about how much of yourselves you can give to the relationship.

stories on older man younger woman

11. Watch out for your emotionality in this May-December relationship

As someone still in your 20s, you are allowed mistakes, misunderstandings, and emotional screw-ups. It’s normal to have a few tantrums, or jealousy and insecurity in relationships. Just because your partner is aged does not mean you can dispose of who you are naturally meant to be. I ask my dear friend, Sophie, who’s dating a guy 14 years older than her, “Do older guys fall in love faster when you’re emotionally mature?” She says, “Yes. My experience dating an older man suggests that to keep up with him and constantly learn, you have to be more alert and mature about your responses.” Remember the following:

  • He may not entertain petty high-school schemes and could be hard on you when you act immature. That’s a big difference between boys and older men
  • 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: The 18 Signs Of A Confident Man That Women Look For

12. You might communicate differently from each other 

Do older guys fall in love faster? To be honest, 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 lay out all their expectations in front of you without a second thought. As a young woman who is still navigating what she wants, your communication may be more elusive, coquettish, and without any serious inclinations. This can make it challenging to build an interdependent relationship.

On the plus side, while dating an older man in your 20s, 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 might 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. That’s what you gain from dating mature men – Unwavering faith and confidence in you and your goodwill.

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 know the ways of the world, you might feel like a newbie. 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 from your older partner

I am sure you remember the epic love story of Monica and Richard from Friends. They went against 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 led to a painful breakup. 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. On the outside, you might say, “I love the man you are,” but in your head, you are thinking, “I wish you spent more time in bed and less time preaching to me about mutual funds and investments.” At a time like this, it is important to try to have realistic expectations from one another.

dating older men psychology
Discuss what he truly wants from this relationship

15. If you’re dating an older man, he would ideally not be judgmental toward you

Is 20-year age gap too much? Is age just a number? Well, if you’re wondering what is it like dating an older man with a 20-year age gap, know that it can be a refreshing experience in many ways. You shouldn’t resist this love thinking about societal perceptions. When you begin to notice older man attraction signs in yourself, embrace your 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. That’s what attracts a younger woman to an older man. These men are aware of what every stage of life brings out in a person and might share a laugh or two reminiscing about their own silliness.  

Key Pointers

  • A younger woman dating an older man will face a unique set of challenges
  • If the older man you are dating has children, it brings you an added obligation to build a good rapport with the kids
  • In all probability, your future plans and your expectations from each other and the relationship won’t exactly align
  • There will be a lot of whisperings about you two and getting your family on board with the idea of this relationship can be a task
  • He may call you out for your emotionally immature actions and patronize you in some ways
  • He is less likely to be jealous of the other guys in your life and communicate his feelings more efficiently than you

Being in an age-gap relationship has its pros and cons. Just like any other couple, you will both face relationship challenges that are unique to your equation. We hope that now you are well aware of what to expect when dating an older man in your 20s. You know the obstacles coming your way – From family to societal judgment, to your mutual differences and financial gap. With these tips for dating an older man, you’ll be better placed to navigate these concerns more skillfully.

This article has been updated in August 2023. 


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. Sometimes, age is just a number.

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 about their priorities and boundaries, it can certainly work.

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