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How To Talk To Older Women: 10 Topics To Get An Older Woman Interested In You


While the fundamentals don’t change, there are a few differences when you’re learning how to talk to older women and get her interested. More often than not, you’ll find they know what they want and don’t have much time for boring dates or conversation.

Of course, that’s not to say older women have a bad attitude — quite the contrary. The straightforward, open communication is refreshing, just make sure you come prepared! If being a great conversationalist isn’t your strong suit, that’s okay, that’s what I’m here for. In this guide, I’m going to give you 10 simple topics to get you started. The best part is, you’ll find they work in just about any situation. These topics will get you by in a text conversation, at the bar or any one of our favorite places to pick up older women.

The Dating Apps For Meeting Older Women Dating Coaches Prefer

Most older women are meeting guys online now, many ONLY look online. They are also a great way to meet and practice talking to older women if you're a little shy. There are a lot of apps out there but not many are great for meeting single older women. These are the best options right now that consistently work for regular guys:

SiteOur ExperienceOur RatingFree Trial Link
Best For Relationships
Experience Highlights
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  • 75% of all online marriages start here
  • 70% of users meet their spouse within a year
  • In-depth signup and matching process
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Best For Casual Fun
Experience Highlights
Experience Highlights
  • The best way to meet women for casual relationships
  • Best results for regular guys
  • Over 60 million active members
  • Not good for long-term relationships
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Decent For Younger Guys
Cougar Life Highlights
Cougar Life Highlights
  • Focused on younger men meeting older women
  • A mix of relationships and hookups
  • Growing
  • Not as popular as eHarmony of AFF
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By the end, you’ll have more than enough to make a start, then you can begin adding your own flair to it. You’ll know how to talk to older women in no time and it all starts here.

How to Start a Conversation With an Older Woman

If you’re just learning how to talk to a woman older than you, this can seem daunting. Like many things in dating, the first time is always the most difficult. After that, you’ll see that it wasn’t such a big deal after all.

Until then, I’m going to give you topics you can use to talk with an older woman. With these in mind and a bit of preparation, it’ll make the whole process that much easier and avoid those boring or awkward conversations.

You can use these topics both in person or online. For best results online be sure you are spending your time on a high-quality site from our list of rated and reviewed dating websites for connecting with an older woman. Here are 10 topics of conversation to get an older woman interested.

How to Talk to Older Women and Get Her Interested

As you’re learning how to talk to mature women, there are a few things you should keep in mind. It’s not that you have to treat them differently. In fact, the advice is essentially the opposite. The less you think about the age gap, the easier those conversations will flow.

This will come with practice as you get comfortable with how to talk to a woman older than you. To get you started, here are the three most important things to remember.

Be confident — she’s talking to you for a reason

If you take one thing away from this article, let it be this point. Confidence is something every single person finds attractive so don’t let her age ruin that for you.

She’s happily engaged in conversation with you and nobody is forcing her to be there, so quit stressing about it! Obviously, she’s comfortable with the gap between you so there’s really no reason to be second-guessing yourself.

Don’t make the age gap a focus of conversation

Age gaps aren’t the taboo they used to be. You’re both aware there’s a gap between the two of you but honestly, it just doesn’t matter anymore.

That said, in the initial stages of conversation, it’s something you’ll both be slightly anxious about. The worst thing you can do is poke at the source of that mild anxiety. If it comes up in conversation, fine, but don’t let it be the focus of what you talk about most. It’s only going to make those anxieties worse and ruin it for you both.

If you’re stuck for what else to talk about, read on! Below you’ll find the 10 of the easiest topics to help build questions to ask an older woman.

Never try to act like an older man

This is another common mistake you might find yourself making as you figure out how to talk to a woman older than you. Like you have to act like the men you think she’d “usually date.”

The thing is, if she seems interested in dating you, at least in this instance, you’re the one she wants to date. Not you acting like someone her age but you, playing the role of you.

Remember, if she wanted to be with an older man, she would be.

Subjects to Talk About with a Girl No Matter Her Age

Feeling a little tongue-tied and lost for words when you’re in a conversation with an older woman? Here are some go-to topics that will almost always keep the conversation flowing.

Her passions

A great way to bore someone to death in a conversation is to roll out the tiresome “what do you do?” Instead, ask her what her passions are. What makes her tick, what gets her excited. Those are the things you want to know, and the things that will spark an interesting dialogue.

Some of the best questions to ask an older woman revolve around topics like this because it’s interesting. She enjoys talking about the things she’s interested in, it’s easy for her to talk about them and it’s interesting for you, too.

TIP: Ask open-ended questions to get her talking. Make mental notes of the things she mentions; you can ask her to elaborate on each one.

Talk to older women about travel and she'll be more interested

Most older women have traveled, and for better or worse, we all bring back exciting stories from those adventures. It’s another topic that’s interesting for you both and something so easy for her to talk about. In fact, research finds that 18% of people want a second date after talking about travel.

It lets her relive her adventures while sharing positive memories with you. Better yet, if you’ve both traveled to the same place, you’ve got endless topics of conversation right there.

Travel is a gateway topic that leads to other topics (like passions, goals, memories and favorites). It’s a conversation that keeps the positive vibes flowing as long as you keep the dialogue on the right track. This is also a great way to start a conversation with an older woman.

TIP: Ask questions. What’s her favorite place? Her most cherished memory? A place she’d return to? Somewhere she has always wanted to go? Where might you two go together, and what would you do?

Her dreams

Almost as important as her passions are her dreams. Some older women feel the pull of their dreams stronger than their younger counterparts. They might feel they’re running out of time to live their “perfect” existence. Talking about her dreams will get her excited thinking of the future. It’s a great way to connect beyond superficial conversation. Talk about how you might fit into her picture-perfect future.


Older women love to give younger guys advice. It makes them feel important and shows you’re open-minded enough to accept her perspective. She knows you have less experience than she does and it’s important that she knows you can be vulnerable. So if you want to talk to an older woman to get her interested in you, asking her for some advice is a great way to do that.

By staying engaged and asking follow-up questions, you’ll show her that you’re interested in what she has to say. Being a good listener is a great way to attract women without talking.

TIP: Maintain eye contact. Try not to break contact until she does. It shows your interest and helps you gauge hers (by her level of eye contact).

Her Goals

Goals aren’t the same as dreams but they are definitely one of the best ways to start a conversation online with a woman. Goals are smaller, more realistic steps towards something she’s aiming for. For most of us, they’re also what gives us a sense of purpose and excitement in life.

You’ll learn a lot about her and have a productive conversation. Who knows, you might even motivate her to chase some of those goals. She’ll be so thankful for your help.

YOUR passions, dreams and goals

Your passions, dreams, and goals are important too. Most older women are keen to know about their date so she’ll probably ask about your passions, dreams and goals. If she doesn’t, that’s okay. You can find a way to bring it into the conversation organically, or wait until the next time she says "hit me up".

Since good conversation is a continual back and forth, you should always be prepared to answer any question you ask.

TIP: Be confident through the conversation. Sit up straight, face her, and speak up while you’re talking. Body language says a lot about who you are. If you’re slouching and talking into your wine, you won’t be the best conversational partner.

Talk to older women about relationships to get her interested

This can be a tricky one but if done right, it’s another interesting point of conversation. Relationships are something you both undoubtedly have in common and they don’t have to be a negative.

Discussing relationships can bring the conversation to an intimate place, breaking down barriers. Begin by talking in the abstract and slowly bring the conversation to be about you and her if that’s the direction you’re both heading.

TIP: Avoid any negative conversation. It’s best to steer clear from talking about exes or any bad breakups you’ve had. On the flip side, you can throw in some dirty talk to turn her on if you think she likes you enough.


If you’re having trouble getting her to bare her soul right away, the media can be a great opener. Try to stray from simple questions like, “what’s your favorite movie?” But many older women have a book that changed their life or a film they watched with a parent when they were young.

If you decide to discuss news topics, err on the side of caution. Try to let her lead the conversation so you don’t end up talking about an upsetting topic. Ask her if she caught any interesting headlines, or if she reads any publications.


You should use this topic with prudence. Experts find controversial topics that incite engaging discussion lead to the best dating outcomes. It might sound counterintuitive but if you think about it, this is just another topic that gets you both engaged, right? Especially compared to superficial topics.

Obviously, you just need to be mindful of how you act in these conversations. Controversy is totally fine but it should never feel like an argument — you’re not trying to “win” the conversation. If you want to talk to older women to get her interested, you don't want to argue. Instead, you just want to touch on some potentially controversial topics to get the emotions going.

TIP: If you get in over your head with controversy, apologize and move on. By attempting humor or defense with someone you don’t know well, you may end up burying yourself deeper.


As long as they’re genuine, everyone likes to receive compliments, just don’t go overboard. This is a very simple habit to get into as you learn how to talk to older women. The best thing to do is focus on things she can control. Rather than talking about her eyes, focus on her dress sense or the way she approaches a topic.

One that will put you in her good graces and give you a chance to start a conversation about why you messaged or approached her. Make sure it’s sincere, and be prepared to repeat yourself in case she rebuffs you.

These tried and tested ways to talk to an older woman and get her interested will almost always guarantee that she’ll open up to you. Whether you’re at a bar, at work or in the company of friends, you can always use these tips and topics to get her interested in you.


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