What to talk about on dates when you’re out with an older woman

It can be difficult to know what to talk about on dates but we give you some tips on both what to do and what to avoid.

One of the many advantages to dating older women is they generally know what they want. That’s great but it also means you need to turn up prepared. That means knowing what to talk about on dates.

You’ve gone through all the effort on the best cougar dating sites, it’d be a shame to waste that by saying the wrong things. If you’re unsure what to talk about on a first date, this is a great place to start. Even the most confident of us can always improve, right?

When dating older women, you want to present yourself the right way. They’re generally looking for maturity, self-confidence, independence and fun. The better you are at demonstrating these parts of you, the better things will go. Whatever you do, try to avoid talking about the age gap.

Here’s what to talk about on dates

In case you get stuck or completely caught off guard, let’s run through some go-to ideas to have on hand. Everybody has their own style so have fun with it, experiment and ‘read the room.’

As with many things in the world of dating, practice makes perfect. Each of these points can be applied to literally any conversation so don’t be afraid to practice elsewhere. The more you practice, the more you’ll do these things without noticing.

Now, having great conversation depends a lot on attraction. If you are still struggling with creating and maintaining that attraction there are a few great books that really helped us with this.

A genuine compliment

I wanted to start with this one because it’s something we’re so often told to avoid. In my experience, handled correctly, an honest compliment can be the perfect springboard to engaging conversation.

What do I mean by ‘handled correctly’? There’s a good reason we’re advised to steer clear of compliments. That’s because they can feel forced and insincere. Instead, here are some basic guidelines for doing it right.

Actually mean it

It sounds so obvious but it’s the most common problem I see and hear with compliments. Rather than compliment her dress arbitrarily, pick something you truly like about her.

This could be anything from interesting nail polish to her vocabulary or wine choice. As long as you actually enjoy it, tell her.

Heck, thanks to my ex, I know far more about eyebrows than maybe I should and this has lead to some great conversation. It’s interesting because it’s rare for a guy to even notice them. She appreciates it because she’ll have invested time, money and pain in shaping them. Weirdly, as I learned more about eyebrows they started to become something I really did notice.

The point is, pick something interesting you truly like and let her know. She’ll appreciate this so much more and it shows you’re paying attention.

Make it about something she can control

The most attractive woman I know has one common complaint after most of her dates: “I’m so sick of guys telling me I’m beautiful or pretty!”

Conceited as this sounds (it really isn’t delivered that way), she has a point. For the most part, her beauty is the result of winning the genetic lottery. For that reason, she’s far more interested in a compliment about even her academic achievements than she is about her overall attractiveness.

Follow up with humor

No matter how you deliver it, compliments will often bring some tension. It’s not your fault, it’s human nature.

The best way I find to handle this is to follow it up with a joke. The aim isn’t to undermine your compliment but to offer it and move on. She’ll recognize what you said while you keep the conversation rolling and lower the tension.

It might look something like this:

You: “I’ve never seen that [watch] model with a white face before. It looks great on you”

Her: “Oh, thanks. I saw it last week and had to buy it. It’s a new release.”

You: “That explains it. I almost bought the pink one last month but it just didn’t match my eyes, you know?”

A silly, off-the-cuff and relevant joke is all it takes. No awkward silence or forced change of topic.

Once or twice is plenty

The other common mistake I see with what to talk about on dates is repetition. While I’m sure it’s meant with the best of intentions, it only serves to make you appear weak.

Admittedly this is a trait more common among younger guys but it’s still worth mentioning. Even if you’re falling head over heels for her, please don’t spend the night telling your date you love every part of her — Cringe!

Instead, try to avoid doing it more than twice. There are no set rules here and maybe the situation allows more in jest but be very cautious. You’re usually better off saving them for future dates.

Her most recent adventure

If you’re stuck for what to talk about on dates, this is another fantastic springboard to use. You’re talking about something she really enjoyed. This means conversation will flow naturally and she’ll be engaged the whole time.

Any time I’m going to use this I won’t just launch into it “20 Questions” style. Instead, I’ll segue in with something brief about myself. The conversation will often turn to her experiences with little to no effort.

For example:

You: “I’m trying to decide between Canada and Japan for my next snowboarding trip. Have you been to either?”

Her: “Hah, I just got back from Japan a few months ago. My butt is still sore from falling over all the time.”

You: “Besides the sore butt, would you recommend it?”

Her: “Absolutely! If you go, you have to spend a few days in Tokyo before you leave. The ramen was amazing. We went to visit . . . [excited story time]”

All it takes is sparking that one exciting memory and you’re good from there.

One thing to remember here is there’s a fine line between choosing interesting topics and manipulating a conversation. Great conversation isn’t about manipulation, just choosing springboard topics you can both relate to. It’ll flow naturally from there.

Take a genuine interest in her as a person

It sounds silly, doesn’t it? The thing is, when you’re stuck for what to talk about on dates this can put you under significant pressure. When this happens it’s easy to get caught up in your own panic and throw common sense out the window.

Take a moment, breath and remember you’re just sitting down with another human. At its core, that’s all you’re doing. In my experience, the more you treat your date(s) this way the better they’ll go.

What is it that makes her who she is? You don’t want to interrogate the poor woman but start with some basics and go from there. For example:

  • If she has an accent, ask about her background
  • What does she do for work?
  • What does she do for fun/excitement?
  • Is she doing anything interesting on the weekend?

By themselves, these are quite mundane questions. They’re only meant to get a conversation going, so be sure to move beyond them fast.

Since you’re not grading her answers, don’t just sit there waiting for her to finish so you can ask the next question. Instead, actually listen to what she’s saying and be on the lookout for interesting segues.

Did she just say “my daughter” a moment ago? Why not ask how old her daughter is? Chances are she’s cautious about the topic on a first date and may appreciate the open discussion. Likewise, be ready to move on if she doesn’t seem so eager to discuss. Either way you, get the point — Every answer has the potential to spark an entirely new conversation.

This concept is often referred to as “conversation threading” and it’s well worth learning. Andrew Elsass covers it quite well in his article Anatomy of a Conversation Part 3: Threading.

Common interests

Yet another point that sounds like common knowledge but it’s even more important with older women. You really want to demonstrate that the two of you share some common ground and can get along well.

You don’t want her leaving the date feeling like you’re too young for her to relate to. The best way to do this is to focus on the common ground you share. Even more so if the age gap is significant.

For example, if you’re 20 and she’s 40 then talking about your college dorm antics for 45 minutes isn’t ideal. Instead, throughout the date be sure to acknowledge your similarities. Maybe you both speak another language or share an interest in a particular sport.

By no means do you have to act like you’re the same age, just don’t let it feel like a teacher-and-student dynamic.


The next time you’re stuck for what to talk about on a date, just remember these easy pointers. Figure out who she is, what she likes doing and chat like the attractive humans that you are. No need to overthink it. You’d be surprised how easy it really is once you get started.

Most important of all, don’t be afraid to take a moment and breathe! It’s normal to be worried about awkward silences. I promise your date won’t fall about because you didn’t speak for 5 seconds.

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