How to Date an Older Woman as a Younger Man

Co-authored by Jonathon Aslay and Amber Crain

Last Updated: November 15, 2025 Fact Checked

Dating an older woman is exciting and you really want to impress her—but how? Older women may have experiences or expectations that you're not used to, so it's understandable if you’re a bit nervous. In this article, we'll share everything you need to know about dating an older woman, from making a good impression to moving forward with a serious relationship. Keep reading for our complete guide to dating an older woman!

Top Tips for Dating an Older Woman

Matchmaker April Davis says that when dating an older woman, you should do your best to enrich her life in some way. Be respectful and find ways to be helpful, whether that means cooking for her sometimes or just taking her out on a fun date. At the same time, show her that you're confident, mature, and self-assured.

1

Be confident.

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Show her that you’re secure and self-assured. An older woman knows who she is, and wants a man who knows who he is, too—no matter his age.^{[1]
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Jonathon Aslay
Dating and Relationship Coach

Expert Interview} Try to avoid saying negative things about yourself, especially around her. Instead, show confidence by highlighting the things that you like about yourself.^{[2]
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- If you aren't feeling confident, that's okay! Using positive body language can help you exude confidence (even if you don't feel it). Even simple things like standing tall, making eye contact, and smiling can make a big difference.

2

Hold your own in conversation.

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Work on being thoughtful, mature, and articulate in conversations. Read up on politics, world news, and other recent events so you start good conversations. Be sure to contribute your own opinions, and don't be afraid to open up about yourself.^{[3]
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- For example, talk about your experiences, memories, or aspirations to show her different sides of your personality.^{[4]
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- You might say, "I love to travel and I hope to do more of it in the future. I think my favorite destination so far has been Rome. So much history and culture there! What about you?"
- Avoid topics that make you sound young, like video games or recent drama with your friends.

3

Take a real interest in who she is.

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Ask questions about her life and really listen to her. Put away your phone, make eye contact, and don’t interrupt her. Show interest by asking her open-ended questions about her childhood, work, friends, family, and hobbies.^{[5]
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Jonathon Aslay
Dating and Relationship Coach

Expert Interview} Give her sincere compliments when she reveals interesting things about herself.^{[6]
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April Davis
Matchmaker

Expert Interview}^{[7]
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- You might say, "I noticed you always have a book with you. Who are your favorite authors? Do you prefer any specific genres?"
- To keep the conversation flowing, try to find common interests that you share. If it seems like you don't have any common interests, steer the conversation back to her. Older women tend to be strong conversationalists, so ask her to tell you more about one of her interests.
- Complimenting her looks is fine, but highlighting her sense of humor or personality shows that you have depth. You might say, "The stories you tell about your friends crack me up. I love hearing your perspective and your friends sound so fun."

4

Be respectful.

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Show her that you have manners and know how to treat a woman. It never hurts to be polite, have good manners, and avoid vulgar conversation topics. Treat everyone around you with respect, as well. For example, be kind and polite to servers, friends, and strangers to prove that you're a respectful person.^{[8]
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- Showing up on time to your dates and putting an effort into your appearance are subtle yet effective ways to show respect, as well.
- Reader Poll: We asked 366 wikiHow readers to tell us which personality trait they find most attractive, and 51% of them said kindness. [Take Poll] When it comes to attracting an older woman, being genuinely nice and respectful can go a long way.

5

Keep the mood light.

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Enjoy the moment with her instead of worrying about the future. She’s probably had her fair share of serious relationships already. Stick to fun, lighthearted topics and make her laugh as much as you can. Show her how much fun you can be!^{[9]
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- You can open up and share serious things about yourself when you’re ready, of course. But early on, try to avoid super serious topics like politics or your future as a couple.

6

Be positive and energetic.

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Impress her with your energy and willingness to try new things. What you may lack in experience or knowledge, you gain in enthusiasm, excitement, energy, and a positive outlook.^{[10]
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Jonathon Aslay
Dating and Relationship Coach

Expert Interview} Show her that there are benefits to dating a younger man, too!^{[11]
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- Embrace new opportunities as they come. For example, if she wants to go to the opera and you've never been, look at it as a chance to experience something new.
- Even if you haven’t done a lot (yet), you can always talk about the things you’re excited about trying in the future.
- When you’re getting intimate, don't focus on your lack of experience in that department. Just enjoy yourself in the moment. If she wants to teach you a few things, be open to that!^{[12]
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7

Put effort into date planning.

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Take turns deciding what to do on dates and come up with fun ideas. Even if you asked her out, you may not know what to do or where to go on your date. Well, what are her interests and hobbies? Come up with ideas about where to dine, what movies to see, or what activities to do together based on things she likes or has mentioned before.^{[13]
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- For example, if she mentions her love of wine, you might bring her to a wine-tasting event or book a tour at a vineyard.

8

Be yourself around her.

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Show authenticity if you want to have a meaningful relationship. You don't need a complete personality makeover to impress an older woman. At the end of the day, you want her to like you for you, not some polished, dressed up version of who you are.^{[14]
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- You can always work on gaining experience, being more mature, and holding your own in the relationship, but you don't need to change yourself.
- Don't worry about her judging you for your interests or hobbies, especially if they're a big part of who you are. If she's dating you, then she'll be curious to hear about your interests, even if she can't relate to them.

9

Show off your independent side.

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Maintaining friendships, interests, and goals is a sign of maturity. Make it clear that there’s a lot more going on in your life than just dating her. Continue spending time with your friends regularly so she knows friendships are important to you. Work toward your goals and share them with her so she knows you're a complex and dynamic person.^{[15]
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- For example, you might mention an upcoming hiking trip you're planning with your friends. If you're working on a passion project, tell her a little bit about it. For example, "I'm really into classic sports cars. In fact, I'm restoring one right now. That's how I spent my weekend."

10

Focus on her, not her age.

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Pointing out her age all the time can make her feel awkward. Most women don’t want to be looked at as older—they just want to enjoy relationships on their own terms. Unless she brings it up, try not to draw too much attention to her age, and avoid bringing up your age difference constantly.^{[16]
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- It's exciting to date an older woman, but if you keep bringing it up, she may get the sense that your heart isn’t in the right place.
- Other people might make comments about your age difference; just ignore them. As long as you're both happy and having fun, there's absolutely nothing wrong with dating outside of your age group.
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

What matters most is being with someone who appreciates you. An age gap doesn't really matter—what counts is finding someone who shares your passions. Besides, if you do end up with an older woman, you may find that her confidence and emotional depth create an attractive combo.

11

Give her space.

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Respect that she's her own person with a life outside of you. It's fine to check in with a quick text when you’re apart, but leave it at that. Let her do her own thing and enjoy herself. To prove that you're mature, try to avoid acting jealous or questioning her about what she's been doing.^{[17]
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- Don't mistake her independence as a lack of interest. One of the best things about dating an older woman is how independent and self-assured she is!
- An older woman has more life experience, which can sometimes mean emotional baggage. For example, maybe she's newly divorced and wants to date casually for now. Try to respect what she's been through.^{[18]
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12

Be upfront about what you want.

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It’s important to be honest if the relationship starts getting serious. If she wants more from you than you're currently able to give, don't string her along or waste her time. Respect her needs, have an honest conversation with her, and part ways amicably.^{[19]
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Jonathon Aslay
Dating and Relationship Coach

Expert Interview} If the relationship is going well and you want to take it to the next level, be upfront with her about what you want.^{[20]
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- You might say, "We've been dating for a few months now and I really like you. I'd love to be an exclusive couple and see where the relationship goes. What are your thoughts on that?"
- A difference in age can mean you're both at different stages of life. Reflect on where you're both at right now. What are the family dynamics like? How does it feel to be together in your social circles? Do your lifestyles complement each other?^{[21]
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  Jessica January Behr, PsyD
  Licensed Clinical Psychologist
  
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Question

How do you know if your age gap is OK?

Jessica January Behr, PsyD
Licensed Clinical Psychologist
Dr. Jessica January Behr is a Licensed Clinical Psychologist and the Founder and Director of Behr Psychology. She specializes in couples and sex therapy. Additionally, Dr. Behr treats those experiencing anxiety, stress, relationship problems, and depression. She holds a BA in Psychology from Hunter College. Dr. Behr also holds a Masters of Science of Education (MsED) in School Psychology and a Doctor of Psychology (PsyD) in Clinical Psychology from Pace University.

Jessica January Behr, PsyD

Licensed Clinical Psychologist

Expert Answer

First you got to understand that there's nothing inherently wrong with two consenting adults being together. More important than the age gap is the fact that the relationship is healthy and comfortable for each of the partners.

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Can a relationship work between a younger man and an older woman?

Jessica January Behr, PsyD
Licensed Clinical Psychologist
Dr. Jessica January Behr is a Licensed Clinical Psychologist and the Founder and Director of Behr Psychology. She specializes in couples and sex therapy. Additionally, Dr. Behr treats those experiencing anxiety, stress, relationship problems, and depression. She holds a BA in Psychology from Hunter College. Dr. Behr also holds a Masters of Science of Education (MsED) in School Psychology and a Doctor of Psychology (PsyD) in Clinical Psychology from Pace University.

Jessica January Behr, PsyD

Licensed Clinical Psychologist

Expert Answer

Yes, but you have to ask yourself why you're worried about that. Do you feel totally comfortable with the relationship? There usually are external concerns, like blending in with family and friends, but the most important thing is how you feel on the inside, especially regarding other aspects that may burden the relationship. For example, older people are usually more financially stable and have children, and those dynamics can affect you.

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Can a younger man be happy with an older woman?

Jessica January Behr, PsyD
Licensed Clinical Psychologist
Dr. Jessica January Behr is a Licensed Clinical Psychologist and the Founder and Director of Behr Psychology. She specializes in couples and sex therapy. Additionally, Dr. Behr treats those experiencing anxiety, stress, relationship problems, and depression. She holds a BA in Psychology from Hunter College. Dr. Behr also holds a Masters of Science of Education (MsED) in School Psychology and a Doctor of Psychology (PsyD) in Clinical Psychology from Pace University.

Jessica January Behr, PsyD

Licensed Clinical Psychologist

Expert Answer

Yes, he definitely can! There are, however, circumstances that might make that challenging. For example, you may have reactions to the relationship or mixed feelings about the age gap. You should look inward and ask yourself if you are genuinely interested in the older person or if there is something else going on. You can learn a lot about yourself through your attraction to this person.

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Make sure you're dating an older woman for the right reasons. Ask yourself, "Am I genuinely interested in this person, or is this more of a novelty to me?"^{[22]
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