Twenty-seven-year-old Amy Anderson says her 50-year-old boyfriend makes a better lover because he's more sexually liberated. But not all older boyfriends are created equal, she warns My first boyfriend was four years older than me, and since then I’ve always dated men who were at least a decade older than me. I met my current partner seven years ago, when I was 21 and he was 44. We started dating at 24 and 47, and I’m now 27 and he’s 50 I think that specific view of sex is something that younger men have. It comes down to the messages we absorb in our society; the messages we’re surrounded by. I certainly grew up thinking that sex went a certain way and that it was a very specific thing, and if you deviated from that, you were doing it wrong.
is a column and podcast series exploring sexuality, gender, and kink with the wide-eyed curiosity of a virgin. We all know your "first time" is about a lot more than just popping your cherry. From experimenting with kink to just trying something new and wild, everyone experiences thousands of first times in the bedroom—that's how sex stays fun, right?
This week, we're talking to Amy Anderson about her experience of dating older men. You can catch My First Time on , , , , or wherever you get your podcasts.
I identify as bisexual, and I’ve always had a preference for older men in particular. My first boyfriend was four years older than me, and since then I’ve always dated men who were at least a decade older than me. I met my current partner seven years ago, when I was 21 and he was 44. We started dating at 24 and 47, and I’m now 27 and he’s 50.
I definitely have a type with guys—much older, long hair, and beards. When I met my partner I thought, Wow. We were friends for years before we started dating, because we were both in relationships with other people. The first time we had sex we’d met up and spent the evening together and realized we’d both been in love with each other for a while and hadn’t acted on it. It wasn’t the best sex, because the first time with someone never is. There’s always that awkwardness and uncertainty.
But it was really fun and playful and explorative: all of those great things. And it’s just got better since. Broadly speaking, older men are less goal-oriented when it comes to sex. They’re less fixated on this narrative that we have of sex in our society. It’s not this idea that you kiss and get naked and then there’s oral and penetrative sex, and that’s it. The older guys I have sex with are less focused on getting to the penetrative sex point as soon as possible, and they’re less focused on orgasm having to be the goal at all times—because orgasms are great, but sometimes they don’t always happen.
Older people have had the time to unpack all the societal stigma that is programmed into sex. They’re more accepting of their sexuality and desires, and confident about expressing them with a partner. I think that specific view of sex is something that younger men have.
It comes down to the messages we absorb in our society; the messages we’re surrounded by. I certainly grew up thinking that sex went a certain way and that it was a very specific thing, and if you deviated from that, you were doing it wrong. For example, I spent years feeling broken because I wasn’t coming from penetration alone.
I think a lot of women share that experience. There’s a lot of stigma that comes with dating someone who’s much older than you. [With] people who say “you’re just with him for the money,” I shut down immediately, because I’m more career-driven and the higher earner out of both of us.
People will always judge you, whatever you do. There’s also a lot of stigma directed at the older man. People assume he’s just a creep who wants to have sex with someone much younger. That’s actually true in some cases, though. People say to me, “Is it not creepy for an older guy to be with a much younger woman?” I reply: “It depends.” I am creeped out by older guys who exclusively date women under 25, because I think, Why? It feels like they’re just fetishizing youth, which isn’t something I’m comfortable with.
I like to date guys who like me for me, not for the age I am. That’s what I have with my partner now—he says, “I would have dated you at whatever age you were.” Dating someone who happens to be younger, as opposed to dating someone because they’re younger, is where the line is drawn between creepy and not creepy.
"I think about the future all the time. It’s hard, and it’s complicated." You can tell if someone is creepy by looking at the person’s dating history—have they dated people from all over the age map? I dated a guy when I was 19 who was 35, and he’d always brag to his friends that he was sleeping with a 19-year-old. Now I realize that was wrong, because he was treating me as a trophy, not a person.
Using a younger woman as a status symbol is a big red flag. Navigating age and gendered power dynamics can be difficult in age-gap relationships. It’s often easy for the younger partner to fall into a subservient role. My partner and I are very careful that we discuss everything from an equal footing. But there are times where I have to check my own internalized stigma and not assume that I should do what he says because he’s older and male.
He’s taught me a lot, and I’ve taught him a lot as well. We have a lot of fun together. I don’t think I’m missing out on anything. We go on holiday; we go on trips; we go out together. I’m not into the standard things that 20-somethings are into—I don’t like going out clubbing, that’s never been my thing. We have enough in common to make it work.
Aligning values and desires is what matters. I think it’s important to acknowledge that age does impact our relationship. Most of the time, it’s small stuff—he’ll make a reference to a band from the 70s and I won’t know what the fuck he’s talking about. The harder stuff to navigate is power dynamics and the possibility of the eventual ill-health and death of the older partner.
I think about the future all the time. It’s hard, and it’s complicated. The scary thought is that there’s the possibility that I may be left alone some day.
It’s impossible to completely find a way around that. Because life does things, and age does things, and people get older and die. My view on it is that I could meet someone my own age, and they could get cancer or be hit by a bus and die. Life is fragile and unpredictable. I have to believe that the possibility of what might happen in 20 or 30 years is no reason to not take the happiness that’s being offered to me now.
best dating man 20 years younger than me about love bugs - What You Must Know Before Dating an Older Man
Why do men date younger women? It’s easy – because these women are more flexible and ready to accept more things in a relationship. Apart from it, they are gorgeous and freshness and full of the youthful energy. So you win a huge number of benefits. But how to make it all come true if you are single? Here is how can succeed. Why do 20-something girls look for older men? They wish someone to be their rock. I bet your life path wasn’t that smooth when you were young. So you can fully understand young women looking for men capable of giving them a hand in problematic situations.
Remember that your potential girlfriend only begins to live so her daily routine is full of challenges. They need a wise friend by their side. Wisdom is not always determined by age, of course. But the younger we are, the more expectations we put on our older companions. A young girl feels much more confident if there is a reliable advisor to whom she can come for backing. For example, if you are keen on , this is what they actually expect.
They long for help and guidance. A younger lady wants her man to teach her valuable things about the world. A man of her age doesn’t have such a vast experience in different spheres of life so this girl struggles to find somebody who would treat her appropriately and share vital knowledge.
The “father” factor isn’t going anywhere. Since the last century, the percentage of divorced couples has been growing so it is a common thing when children stay with their single mothers. Girls who were raised in incomplete families typically attempt to compensate the lack of fatherly attention. They are tired of seeking the true love within their age group. Women looking for older men are often motivated by their past missteps.
Younger guys typically concentrate on their own education, careers, personal issues and inner evolution. They do not have really much time for caring about someone else as it should be.
They hope to explore their sexuality. As a rule, women experience the peak of their sexual activity in their late 20s-mid 30s. Thus, a girl in her early 20s or younger is not fully aware of her preferences and secret urges in bed.
As an older partner, you can help her learn her body and its needs and show many different ways to get pleasure. They do not see their age mates as dating materials. Some girls just do not turn on by men close in age with them – for various reasons.
The younger we are, the more selfish we are, which makes love searches difficult. How to attract a 20-something girl in 8 steps Make your age your biggest plus.
Men in their 40s or 50s are often afraid of approaching younger women as they feel insecure about age gaps. However, the impression you make on ladies completely depends on who you are, not on how old you are. Show her that you possess the best manly qualities and know what life is! Take care of your physical shape. Yes, your inner world and intellectual capabilities may be impressive yet they become unnoticeable if you fail to keep yourself fit and attractive. Do not forget about getting a good wardrobe too since a young woman wishes to date a handsome man.
Regardless of how many years you have apart, you should look good together. Display success. People tend to gain experience and accomplishments with age. What about yours? I guess there is something to be proud of in your life. Let her know about your professional and personal achievements so she will see how smart, strong, witty and determined you are.
Keep your mind open. As we get older, our psyche becomes more rigid – it means we tend to listen to ourselves only and reject anything that brings changes to our life.
Try to stay mentally young as long as possible and 20-something women won’t see you for an old grumbler. Yes, you can become their teacher but you should be their peer as well. Stay active and bold. The fact you’ve achieved something in your life doesn’t mean you can now retire and spend your whole days sitting in an armchair by the fire – unless you wish to remain a single older man, of course. To make your romantic life bright, you have to make moves. Continue to develop as a person.
This is the main tip to give if you want to know how to remain attractive for women. Read, travel, find new hobbies, meet people – this all is necessary for you to grow. It is never late to learn new facts about the world and the human race; not to mention it is very exciting. Gain from your inborn charisma. Not all older men are the same, right? Younger girls fall for exceptional ones! Everything you have inside can make you stand out.
Be decisive and advance your wooing skills if you are about to meet the woman of your dream. By the way, if dating Russian women is your purpose, keep in mind they love charismatic men very much! Be mindful towards her. Nothing touches a woman’s heart more than your sincere devotion. If you prove yourself as her trustworthy protector and helper, this young girl can get to thinking about a romance between you two. How to date a young girl: 9 key rules Surround her with your support and protection.
As you know, a young girl – subconsciously or consciously – wants to get some fatherly love along with man’s devotion. Give it to her!
Behave like her chevalier. The younger generation often forgets about good manners. As a representative of the “old school” of wooing, you can easily charm a young Russian lady. Encourage her self-growth. Young people long for more knowledge and understanding of the reality. If a 20-something woman chooses you as her romantic partner, you can help you become a better person. Learn new things from her. A relationship becomes harmonious when lovers exchange their feelings and thoughts.
Your significant other is also capable of broadening your circle of interests and knowledge. Stay away from controlling her. This is one of the most important rules to follow while dating a 20-year-old woman. If you put pressure on her beloved one, she will become detached and irritated. Keep the balance between care and pursuit! Let it all develop step by step. Young women can be frightened by your increased attention; this is absolutely normal.
There is no sense to rush it – give her time to get to know you and find out more about her too. Take the lead. To impress a young Russian girl, you should take the initiative. Do not hesitate to make the first steps towards her if you really feel there is the connection between the two of you.
Raise your confidence. When it comes to dealing with younger women, confidence should become your main weapon. Do not concentrate on your age peculiarities or your personal flaws. Nobody is perfect but this is what makes any of us unique.
Accept the possible changes. Your partner will get older and she will develop new qualities, opinions, interests and skills. Be ready for these fruits of her evolution. I don’t try to scare you! Just consider she won’t always be an inexperienced immature girl. To wrap up. So this was our comprehensive recommendation on how to date younger women. Learn these simple tips well and remember that dating a 20-year-old girl was never too smooth.
Her lifestyle is hectic; you should invest some efforts to become part of it!
Dating is always fun. To date a younger man can be even more exciting. But before you start dating a younger man, probably who is 5 or 10 years younger than you, you need to know what to expect.
Your relationship compatibility with your younger man is what takes your love life to the next level. As an older woman, you must know both the pros and cons of your dating life. So, here are top 20 things that you need to know if you are dating a younger man.
Younger men are more fun and cute when it comes to impressing their women on dates. He will be able to make your life exciting and you will end up looking for spending more time with him. He will bring about the good old dates where it was all about fun and not about something serious. So, the best advice would be, if you are going on dates with a man who is 5 or 10 years younger than you, cherish it.
The older we get the more baggage we hold for ourselves. While dating younger men you are prone to be with a man who has lesser baggage. This is one of the biggest pros and cons of dating younger men. The younger he is (5 or 10 years), he would have lesser baggage. Lesser baggage also means lesser relationship experience which means you will have to improve his relationship skills which can be a lot of work.
The older you get the more control you have over your relationship. You will never be afraid to say NO when it comes to fooling around in your dating life. With your experience, you will find that you will have to handle your connection as younger men are not really good when it comes to relationships. The best advice would be to take the necessary steps when it comes to shaping up your perfect love life.
If your man is younger than you, say some 5 to 10 years then probably there is a huge lifestyle difference between the two. As older women, you will find yourself focused on your relationship and value spending time with your man, on the other hand, he will be into his friends and flirting. This might create a little chaos in your relationship. This is one of the major con that you must consider before dating a younger man.
If you are dating a younger man, then you would have known by now that your man is not ready to commit. He might be battling his own commitment issues and will not be able to take the next big move. Now, this might not be suitable for all younger man, but mostly younger men will look for adventure before getting committed.
The best advice would be, as an older woman, you must know when to take a call. If you are an older woman and are dating a younger man and when your relationship turns all serious there might be a lot of confusion when it comes to having kids. If you are an older woman who is in her 40's and let's say your man is 10 years younger than you, he will want to have kids but you might not be ready to take that big step.
This is one of the major flaw while you are dating a younger man.
I fell in love with a man a decade younger than me.