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How to Date an Older Woman: 10 Tips to Impress Her

January 6, 2023
How to Date an Older Woman: 10 Tips to Impress Her

Dating an older woman can be a very rewarding and enriching experience, but it can also bring its own unique set of challenges. Older women tend to different perspective on life to younger people and this can add a unique layer of complexity to the dating dynamic. Compared to dating someone the same age as you, dating an older woman can require you to step outside your comfort zone and try new things. For example, she's likely to be financially stable and have more life experiences. She may have children already, and friends who are also older than you.

But don't be worried. In today's society, people largely agree that age is just a number, and although there may be many things that set you apart from each other, that's largely just because you are at different stages in your lives. Through time, and through following these simple steps, you'll find and accept many things that you also have in common.

1. Show Respect

Make sure you show respect for your older woman by treating her with kindness and courtesy. She deserves to be treated like the mature, beautiful person that she is!

Speak to her respectfully, and if you disagree with something she says or does, politely express your opinion.

When dating an older woman, it is important to show kindness and courtesy. First, recognise that she may approach activities differently than someone younger would. Be understanding and willing to learn from her perspective and engage in dialogue when decisions need to be made. Also, show respect through verbal and body language. Take care to listen actively rather than just waiting for your turn to talk.

Show gratitude for everything you do together, no matter how big or small. Lastly, remember that the smallest acts of kindness can go a long way—from bringing her a cup of coffee in the morning to having flowers delivered on a special occasion. Doing these simple things shows you care about her and honours the relationship.

2. Be Confident

One of the most important things when dating an older woman is confidence. She's likely been dating for a while and knows what she wants out of a relationship - so don’t be afraid to explore her feelings and state your opinions.

If you are considering entering into a relationship with an older woman, developing your confidence before you take that leap can be extremely beneficial. Feeling sure of oneself and confident in the potential relationship is key for lasting connection and happiness. Start by recognising the valuable traits and experiences that each partner adds to the equation, regardless of the age difference.

Consider focusing on the positive aspects of “catching up” from different places in life, rather than being overwhelmed by the gap between them, which may prevent either person from making all they have to offer accessible to one another. Being aware of where each person has come from is important to create understanding in a relationship like this.

Additionally, connecting around shared values helps build connection and enthusiasm for each other as peers with commonalities. With clear communication and mutual respect, any couple can develop their bond into something strong and special—even if there happens to be an age difference between them!

3. Ask Questions

Let her know that you're interested in learning more about her life, family, friends, and views on dating and relationships. You can do this by asking thoughtful questions and showing genuine curiosity. Don’t be afraid to ask her questions about her past dating experiences or her life in general - this shows that you are interested in getting to know her.

While we're not all strong conversationalists, expressing a genuine interest in learning more about an older woman's life experience and views on dating and relationships is an excellent way to show her that you care and are interested in learning about her. It is important to take the time to really listen to her stories and perspectives, while ensuring that the conversation flows naturally.

Furthermore, asking thoughtful questions in order to have meaningful conversations will demonstrate acceptance for who she is as a person. Additionally, maintaining eye contact, smiling, and providing positive feedback throughout the conversation will - of course - show her that you are genuinely interested in hearing her thoughts.

To ensure that the exchange is rewarding for both of you, try to keep your chats focused on topics you both enjoy or experiences you share.

4. Be Supportive

It's important to be supportive of your older woman, especially if dating a younger man is new for her. Let her know that you are there to listen, understand, and provide emotional support if needed.

Supporting the woman you are dating is essential for a successful relationship in any age group. It’s important to show her that you recognise she has more life experience, steadfastness, and possibly worldly wisdom. This could be through complimenting her on important accomplishments or praising particular values she holds dear.

Treat her as an equal in all matters - demonstrate appreciation for her opinions and encourage her to make decisions independently of your influence. Offer emotional support when needed – be willing to listen attentively to whatever she is going through, from dealing with major life events to small everyday frustrations.

Show interest in passions outside of the relationship she may enjoy like hobbies, reading, travel etc., but only if it's something that genuinely interests you too. Put forth the effort to integrate into their existing social circle if you haven't already interacted much with them during your courtship.

Developing such bonds will surely bring your relationship closer and show your partner that you care about the people that matter to them most!

5. Take Initiative

Show your older woman that you're interested in dating her by taking the initiative to ask her out. She will appreciate your confidence and initiative!

Showing initiative in a relationship is important for both parties involved and with the older woman you're dating, it could be critical to its success. You should demonstrate your enthusiasm for her and communicate how much she means to you by finding thoughtful ways to show that you're open-minded and considerate of her wants and needs.

That may entail coming up with creative date ideas, initiating conversations about things that matter to her, displaying your knowledge and understanding of topics close to her heart, or participating in activities that she enjoys. Although these initiatives require extra effort on your part, the rewards of strengthening your bond are well worth it!

6. Be Open-Minded

Don't be intimidated by dating an older woman. Be open-minded and willing to learn new things from her, as she probably has a lot of wisdom to offer. Being open-minded while dating an older woman will ensure a healthy relationship dynamic based on mutual acceptance.

Absolutely no one is perfect and when it comes to dating an older woman, being accepting is key. Acknowledging differences in opinion, values, respect and ideas can help foster a positive relationship. It's essential to remember that although there may be disagreements, allowing yourself to be more tolerant of those with varying viewpoints serves as the basis for a healthy dating relationship.

Additionally, make the effort to understand her background and experiences , since, by virtue of her age, she has likely seen and experienced more relative to you. Don't worry yourself with any antiquated notions about age gap between you two—she likely won't bring them up! Instead embrace both the similarities and differences that exist between you in order to evoke understanding without judgement.

When it comes to intimacy, it's likely that she's also more experienced when it comes to sex. Rather than be intimidated by it, or take charge, let her lead. Revel in this wonderful opportunity you have to have a sex relationship with a confident, experienced older woman!

We mentioned before that she'll most likely already have a family. Taking time to explore this and, when the moment is right, to want to get to know them is a sure sign to her that you're keen to stick around.

7. Go Out and Have Fun

Show your older woman that dating can be fun! Suggest activities like going to a movie, out for dinner, or attending an event she may enjoy.

If you are looking for the perfect date experience, consider planning something unique and exciting with an older woman. Perhaps start the evening off by taking a stroll through a nearby botanical garden or visiting your local museum of art. Viewing pieces of creative expression that inspire conversation often leads to great memories and experiences.

If you would like to end the date on a lighter note, then consider attending a comedy show or going to an outdoor comedy club where you can share laughs and conversations that will bond you together.

Whatever activity you choose to do with your special woman, make sure it is something special and memorable.

8. Compliment Her

Make sure you let her know how attractive and amazing she is. She is likely to appreciate that you notice her and want to make her feel special.

Complimenting an older woman you're dating is a great way to show your appreciation for the relationship. A simple act of saying ‘thank you’ or ‘I appreciate you’ can go a long way, as any woman would be thrilled to hear genuine compliments from her partner. If she has recently finished something significant like a work project or creative endeavour, commenting positively on it may make her feel important and appreciated.

Additionally, showing admiration for her wardrobe choice or other related matters is always helpful in making her feel good about herself. Ultimately, regardless of the avenue taken, having words of encouragement for your older significant other will solidify an unbreakable bond and make for a strong relationship that stands the test of time.

9. Give Gifts

Giving your older woman gifts is a great way to show her how much you care about her. Surprise her with a bouquet of flowers or a box of chocolates to show your appreciation for her.

It can be hard to find the perfect gift for someone you're dating, especially if they are older. Mature women tend to prefer meaningful and personal gifts that show you understand them and their interests.

For example, a one of a kind piece of jewellery that speaks to her hobbies or tastes goes a long way in showing your efforts.

A bouquet of her favourite flowers or some handmade souvenirs are also great options.

Alternatively, if you know a particular artist she loves or if there's particular interest she has, getting tickets to an event involving them or going on an experience together is sure to make it memorable.

Overall, no matter what gift you choose, remember that making it thoughtful and unique is key when shopping for the special lady in your life.

10. Be Patient and Understanding

Dating mature women can be an uncomfortable experience for some younger men, so make sure that you are patient and understanding during the online dating process. Let her know that it's completely okay to take things slow, and that you are there for her if she needs anything.

When dating girls with more experience, developing patience and understanding is essential for successful and enjoyable relationships. This maturity will allow the relationship to develop even through tough times.

Open-mindedness and flexibility are key traits that need to be practised as both parties will have different perspectives on how to approach various situations. Taking the time to understand each other's point of view allows for mutual learning and understanding while leaving room to grow together.

Being patient and understanding often yields greater rewards, such as a deeper connection, trust and a lasting partnership.

What Are The 10 Best Dating Sites For Older Women Looking For Younger Men

At Best10DatingGuide, we're here to help you join the right online dating site for you. So our article wouldn't be complete if we didn't tell you what we think are the best dating websites and dating apps out there when it comes to dating older women. Be warned - some of these sites are less tame than others, offering you the opportunity to date casually!


This dating app offers a variety of features that make dating an older woman easier and more enjoyable. It also provides access to various types of singles, such as those seeking a serious relationship or casual dating.

2. EliteSingles

EliteSingles is a dating site that caters to the needs of mature dating singles, and it has a wide variety of search options to help you find the one that’s right for you.

3. OlderWomenDating

This online dating site is specifically tailored towards older women dating younger men, and it offers a safe and secure platform for users to interact with each other.

4. AgeMatch

With AgeMatch, dating an older woman no longer has to be a challenge. This dating site is designed for those who want to date someone younger or older than themselves, regardless of the age gap.

5. MillionaireMatch

If your dating an older woman with wealth, then you'll be glad to know that MillionaireMatch exists. This dating site allows you to find wealthy women and men who are looking for dating opportunities.

6. CougarLife

This cougar dating site caters specifically to mature dating singles, providing a secure space for users to meet and interact with each other.

7. DateRichWoman

This dating site is catered towards the needs of men or women looking to date a wealthy older woman. It provides a safe and secure platform for dating an older woman.

With this cougar dating site, dating an older woman is easy and fun. It has many features to help make the process smoother, such as private messaging, advanced search options, and more.


Described as a "toyboy" or "cougar" dating site, this is designed specifically for older women dating younger guys, and it offers a safe and secure platform for users to interact with each other. It typically has attractive older women with more experience looking to find younger friends with benefits.


EagerCougars is open about the fact that its older women members are looking for younger guys for short term relationships. It provides a safe platform with thousands of members from around the world.

We hope you find this advice useful if you are thinking of dating older women, and gives you a bit of a sense of what to expect. Cougar dating services can be a fantastic place to meet other members looking for the same experience as you. Give any of the ones a go that we recommend, and don't forget to check back here regularly for updates and news about new services you might be interested in trying out.

Jaqueline Gutmann
Jaqueline Gutmann
Jaqueline writes for Best10DatingGuide and is an experienced life and dating coach. Jaqueline's passion is getting the most out of your dating experience, and when she's not writing you can find her trail running in the Swiss Alps.