How to Flirt With Older Men

Co-authored by John Keegan

Last Updated: August 24, 2024

To some women, men their own age just can't hold a candle to an older man. But you may not be sure of how to flirt with him. After all, he's in a different stage in his life, and you might not have much in common with him. Luckily, talking to an older man is more about having confidence in your youth than having life experiences in common.

Part 1

Part 1 of 2:

Making an Older Man Feel Comfortable

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1
Make him feel like a person, not an age. When younger women talk to older men, they sometimes feel the need to explain in detail what precisely they like about older men. This might make the man feel like you're after a "type," not a person.
- Instead of starting with why you're attracted to older men in general, focus first on why you want to talk to him specifically.
- Do you like his salt and pepper hair? Is he particularly well-dressed? Did you overhear him talking about a subject that interested you?
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Address the age difference if it comes up. You want him to feel relaxed and comfortable with you, so let him decide whether he wants to talk about the elephant in the room. If he never brings up the age difference, that's fine. Discussing other subjects suggests you're not attracted to each other because of your ages. But, if he does bring up how much younger you are than him, don't shy away from the conversation.
- After assuring him that you're interested in him for himself, you can move on to a discussion of why you may prefer older men in general.
- Don't dwell on past relationships, but speak in broad terms about what you think older men have to offer that men your age don't.
- Financial stability should not be the focus of this conversation. Think about all the other things older men can offer — emotional stability, perspective, a calmer lifestyle.
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Let him decide if he wants to talk about his job. Different men will have different approaches to dealing with the issue of financial stability. Let him choose how much he wants to reveal about his employment.
- If you steer the conversation toward his job, he might wonder if you're flirting with him only because you think he's rich.
- On the other hand, he may want to show off his great job. Let him use it as a flirting asset, just like you're using your youth!
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Show financial independence.^{[1]
X
Research source} Whether he has a great job or not, he may not want to talk to a younger woman if he thinks you need him to support you financially. Even if he doesn't choose to talk about his job, make a point of telling him about yours.
- Don't discuss the specifics of your salary, of course. But talking about your job lets him know subtly that you're a workingwoman who can take care of herself.
- If you're at a bar and he tries to pay for your tab, thank him, but laugh it off. Say, "You're so sweet, but you don't have to do that!"
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Respect his opinions. If there's one thing adults of all ages can agree on, it's that there's nothing more irritating than a younger person who thinks they know better. While you don't have to agree with everything he says, don't contradict him constantly. Some people worry about growing "out of touch" with current ways of thinking as they get older. You want to make him feel "experienced," but not "old."
- A good way to deal with a difference of opinion is to treat it as a learning experience. Instead of emphasizing how much you disagree, ask him to explain why he feels the way he does.
- Listen thoughtfully and openly. You don't have to change your mind, but you've shown him that you respect him enough to want to understand him.
- Of course, if he holds personal opinions you find offensive, feel free to give him an earful and walk away. Don't sacrifice your principles just to date someone.
EXPERT TIP

John Keegan
Dating Coach
John Keegan is a Dating Coach and motivational speaker based in New York City. With over 10 years of professional experience, he runs The Awakened Lifestyle, where he uses his expertise in dating, attraction, and social dynamics to help people find love. He teaches and holds dating workshops internationally, from Los Angeles to London and from Rio de Janeiro to Prague. His work has been featured in the New York Times, Humans of New York, and Men's Health.

John Keegan
Dating Coach

Who knows—you might even find his confidence attractive. Older men may exhibit confidence and a deeper ability to process emotions. Emotional intelligence develops with experience, after all!

Part 2

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Putting Your Best Foot Forward

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1
Engage him in conversation. Although you should respect his opinions, you also want to show him that you have a mind of your own. A difference of opinion can often result in an absorbing discussion instead of an argument. What man wouldn't go crazy for a woman who can turn a disagreement into great conversation?
- Relax your facial expression to let him know you're not getting worked up about any differences of opinion.
- Be able to laugh about how far apart you might be on an issue.
- If you're lucky, you might have found someone who's actually on the same page as you. In that case, celebrate!
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Dress your age. Your youth is one of your biggest assets when flirting with an older man. Use it to your advantage! When you get ready to go out at night, wear fashion styles that set you apart from older women. Of course, you shouldn't dress like a teenager. You don't want him thinking about you dragging him to One Direction concerts! Wear clothes that look good on a woman in her mid twenties or thirties, but might look a little strange on a woman in her forties.
- To older men, the most attractive thing about young women is that they're already at the ideal age. You don't have to try to look older or younger. You're already in the sweet spot!
He sees you, and he can already tell you're a younger woman. You don't have to play up your youth to get his attention in conversation. Own your age, but don't make it the central focus of the conversation. Highlighting it repeatedly (“That's my dad's favorite song!”) might make the conversation grow tiresome for him. He might also start thinking of you as a pretty face without substance. Instead of spending your time talking about how young you are, focus instead on how mature you are for your age.
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Don't hide your youth, either. It might seem like you don't have enough in common with him to hold his interest. For example, he may bring up children, mortgages, 70s music, or any number of other things you have no experience with. Don't fake your way through the conversation, pretending you understand what parenthood is like. He'll see right through it.
- Make sure you don't come off as childish. You're young, but not frivolous. Instead of saying "I have no idea how mortgages work," steer the conversation toward something he wants to talk about. Ask him what he likes about home ownership, for example.
- Even if he focuses about how hard something is, just smile and say "I haven't experienced it yet, but I can't wait to."
- If he wants to share an experience with you, agree to keep an open mind: “I don't really like music from before the 80s, but I'll give it a shot if you think I'll like it.”
Older men have had more time to figure out who they are, and they're usually secure in their personalities, likes, and dislikes. They want the same thing in a woman, even if she's younger. Listen to him talk about himself, but also share who you are. If you're actually looking for a calmer lifestyle than the one you led when you were younger, say so. If you still enjoy ripping it up with the girls on the weekend, own it. Don't apologize for it — it's part of what makes you you.
Don't challenge him to a staring contest, but connect with him through his eyes. Maintaining eye contact shows that you're both confident in yourself and drawn to him.
These are very personal areas on the body. Even our oldest, closest friends don't usually touch our necks. The neck and hair are off-limits to everyone but sexual partners, for the most part. Draw attention to them to let him know what you're thinking.
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Be aware of your body language. This applies to all flirting, not just flirting with older men. Note that much of this body language might suggest you're interested in a sexual relationship. Consider his feelings and your personal safety. Don't make him think you're sexually interested if you're not. But if you are interested, what you say with your body might come across more clearly than what you say with your words.
- Draw attention to your lips: nibble your lower lip, purse your lips when you're thinking, or apply a nice, bright lip balm. Make him think about kissing you.
- Don't be too shy to touch him: rest your hand on his when you laugh at something he says, or place it on his shoulder when you lean in to share something private.
- Don't cross your arms: this makes you seem closed off.^{[2]
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  Research source}
- Lean toward him to close the distance between you.

Attract and Date an Older Man with this Expert Series

There's nothing wrong with an age gap in an adult relationship as long as both people are on the same page. Learn how to attract and date the man of your dreams with this expert series.

1

12 Things to Consider Before Dating an Older Man

2

Date an Older Guy

3

How to Handle an Age Gap in Your Relationship

4

13 Explanations for Why Older Guys Like Younger Women

5

Why Am I Attracted to Older Men?

6

Attract an Older Guy

Expert Q&A

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Question

How can you tell if an older man likes you?

John Keegan
Dating Coach
John Keegan is a Dating Coach and motivational speaker based in New York City. With over 10 years of professional experience, he runs The Awakened Lifestyle, where he uses his expertise in dating, attraction, and social dynamics to help people find love. He teaches and holds dating workshops internationally, from Los Angeles to London and from Rio de Janeiro to Prague. His work has been featured in the New York Times, Humans of New York, and Men's Health.

John Keegan

Dating Coach

Expert Answer

Pay attention to his body language too to see if you're a good match. The way he talks and moves his body can be a good indicator of whether there's chemistry between you.

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Warnings

Though the laws vary from state to state, it is illegal in the US for adults to enter into sexual relationships with minors.^{[3]
X
Research source} If you're under the age of 18, wait until you're a legal adult to flirt with older men.

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