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Things To Talk About On A First Date With An Older Woman

An older woman discussing things to talk about on a first date

Coming up with things to talk about on a first date is your next step now that you have chosen a great location for a first date using our guidelines found HEREIf you have not dated older women in the past you are in for a treat.

One of the best reasons for dating older women in the first place is more interesting and engaging conversation. These women have life experience and maturity that you just can't find in most younger women.

Before your date you should plan out a few topics of conversation you want to cover as well as a few stories that you want to share. Since this is your first real get-together you want to keep the things to talk about on a first date light, engaging, and preferably with a lot of humor thrown in.

There are a lot of different topic of conversation that could fall under these guidelines but here are five that almost always get great results. With the exception of travel (if you have not had an opportunity to travel much), anyone should be able to have an interesting conversation about these topics.

Things to talk about on a first date

Okay, so you took our advice on where to take an older woman on your first date. Now it's time to talk about what you'll actually talk about when you're there. Here are some ideas.

Her passions

Among the best things to talk about on a first date is passions. Everyone loves to talk about their passions in life. This is especially true for older women. When cougars are talking about their passions in life they are engaged, excited, and tend to feel more connected to their conversation partner. This is exactly what you want on a first date.

Discussing her passions is also a great way to get past the typical small talk barrier very quickly. The last thing you want when thinking of things to talk about on a first date is to spend 30 minutes or an hour on surface-level conversations like the weather. Get her excited by talking about what excites her!

It might take a little work to really tease out what her passions are but once she gets going on the topic you will be thankful you made the effort. It might even lead to a conversation about second date ideas!

Your passions

Passion is contagious and exciting. One of the most attractive things about dating younger men is that they tend to be more optimistic and passionate than their fellows who are ten or fifteen years older. Use this to your advantage! When you're with an older woman, her interest in your passion should be one of the things you can expect on your date.

Being able to speak eloquently and passionately about your passions in life is extremely attractive. You are going to be more confident speaking about your passions and likely know a lot of interesting things in that area as well.

Some passions are naturally going to be more exciting than others (scuba diving, race car driving, etc.) but don't be discouraged. You can have a great conversation about more mundane passions by sharing WHY it is so fascinating to you. You do want to be careful if your passions might make you look childish or immature when dating older women. If your passion is playing video games or collecting action figures you may want to avoid those and focus on more "adult" passions and pursuits until you get a better sense of what the cougar you are dating is open to.

Dreams and goals

Optimism, hope, and passion are characteristics that come up again and again when older women discuss what they like about younger men. When coming up with things to talk about on a first date these characteristics can really be leveraged when talking about hopes, dreams, and goals.

While the women you are dating may be from a different generation she still has dreams and goals she is working toward. Just like when talking about her passions, when cougars are talking about their dreams and goals they are engaged, excited, and tend to feel more connected to their conversation partner.

When you are talking about dreams and goals you are able to have a fun and interesting conversation about what the future may bring. This type of light and creative conversation is not something most older women get to have very often and can really set you apart.

This is also where you can share your own dreams and goals to show that while you are younger than her you are by no means a boy.


Most single older women dating younger men love to travel and are open to new adventures. Talking about past trips allows her to relive the excitement she had during those days while sharing it with you. If you have traveled to similar place you can easily have an entire conversation about your experiences and form a small bond as a result. Travel is without a doubt one of the most common and interesting things to talk about on your first date.

Again this is about focusing on a topic that is interesting, exciting, and fun. If you run out of things to talk about from past trips you can start talking about planned future or trips or "bucket list" trips that you want to have before you die.


Women love talking about relationships. Talking about your relationships with you family, friends, and former love interests can make very intimate conversation. Learning about mature relationship dynamics is one of the reasons you should date an older woman!

Just keep in mind that when you're talking about relationships, you want to focus on the good relationships and stay away from talking about any one relationship too much (mother, bad breakup with ex, etc.) to avoid coming off as obsessed.

Talking about her experiences as an older woman dating younger men and yours as a younger man dating older women can also be very interesting.

These five are just a few of the things to talk about on a first date that can be engaging and fun. You can also see some of the biggest conversational mistakes HERE. When dating older women there is no "one size fits all" approach especially when it comes to things to talk about on a first date. Spend a little time brainstorming ideas and have a few subtopics for each to discuss incase the conversation stalls or grows stale.

Our Best Online Cougar Dating Sites Review is a great place to find older women dating younger men if you are still in the beginning states and not just looking for things to talk about on a first date. There are many fake sites out there that you want to avoid that can be hard to spot. You will also find Cougar Life reviews, Match.com reviews, and eHarmony reviews for those most interested in dating older women.


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