How Do I Make a Move on an Older Woman (5 Ways Forward)

When it comes to pursuing an older woman, it’s not uncommon for questions and uncertainties to arise.

How do you make your intentions clear without coming across as presumptuous or inexperienced?

Well, fear not, because, in this article, we’re about to delve into the art of making a move on an older woman while respecting her boundaries and creating a connection that transcends age.

Whether you’ve been hurt by an older woman or are simply curious about the dynamics involved, we’ll explore the dos and don’ts, share some invaluable tips, and help you embark on this exciting journey with confidence.

So, let’s uncover the secrets to approaching and winning the hearts of an older woman with grace and charm.

1. Carry yourself with confidence

When approaching an older woman, keep your head up, pull your shoulders back, and stretch your back.

This will help you have an air of confidence that will make you seem attractive to an older woman.

Try giving yourself a motivational speech before approaching her.

An instance of this would be saying, “I’m adorable, intelligent, and humorous, so I should simply be authentic!”

Older women tend to prefer confident partners.

Apart from becoming more confident themselves, they have had plenty of time to experience the complexes that come with insecurity.

Likewise, if you come across as insecure, it might seem like you’re looking for a motherly figure and not a partner.

2. Praise her

When talking to an older woman, pay attention to exactly what attracts you to her and then turn it into a sweet compliment that’s specific to her.

As much as possible, try to focus on the way it makes you feel or the qualities it projects.

Compliments of this type can mean much more than simply a comment about her physical appearance.

Let’s say you really like how she laughs warmly.

You can say to her, “You always make me smile with your wonderful sense of humor!”

If you want to compliment how she looks, focus on things she is wearing, like her hairstyle or her outfit.

Complimenting her smile or eyes is nice but kind of common.

Try being more creative.

For instance, if she’s telling an interesting story, you could say, “I could listen to you talk all day!”

3. Plan a nice date based on what you learn about her

Before the date, spend a little time texting or talking to her so you can get an idea of what she likes.

Then arrange a nice date based on it. Just remember to also plan around what you feel comfortable with.

It will be obvious if you are too far out of your comfort zone.

For example, if she likes gourmet food and you’re comfortable with it, you could take her to a fancy restaurant in your area.

However, if you can’t pay the bill or don’t feel comfortable in a gourmet setting, she may feel uncomfortable.

Therefore, it would probably be best to plan something else.

Try to think of dates she might not expect.

For example, if you’re an outdoor lover, you could plan a casual hike or an evening boat ride.

4. Kiss her at the end of the date in case things are going well

Older women often appreciate a direct approach.

If you’re not sure if it’s okay to kiss her, try leaning your face close to hers while looking at her lips.

If she leans toward you too, it’s probably okay for you to kiss her.

However, if you’re still unsure, try saying “I’d love to kiss you right now”.

If she pulls back at the height of the kiss, you should give her a chance to think for a moment, but you’ll also leave her wanting more.

5. Be bold

You must be a man who knows what he wants and is not afraid to ask for it.

Always second-guessing, murmuring, or waiting to say what you think could cause an older woman to start looking for someone more assertive.

You should feel comfortable telling her what you would like her to do on dates, letting her know if she hurt your feelings, and asking for what you want.

Being assertive means that your voice should be firm and clear when you say something.

Speaking very softly or struggling with your words will make it difficult for you to be assertive.

You shouldn’t interrupt her when she talks, but you should feel comfortable expressing what you’re thinking when it’s your turn to speak.

What Questions Should I Ask an Older Woman?

Here are the questions to ask an older woman:

1. I like your name, why did they give it to you?

Almost all names have a story behind it.

This will help you get to know her and her family a little better.

2. What has been your favorite vacation?

We all love going on vacation and talking about what we like most about it.

Asking this question on a first date will open up a conversation about where your date has traveled and will allow you to see if you both like the same type of vacation destination.

3. What is your dream travel destination?

Talking about travel always works.

According to a study, 18% of partners who talked about travel on their first date wanted to go on a second date.

By contrast, less than 9% of partners who talked about movies wanted to date again.

4. What are you currently obsessed with?

Whether it’s a book, a TV show, or sports, chances are there’s something she is currently very interested in.

Older women love to share their interests and it’s a good way to see if you share any of those same interests.

5. What sort of things do you find funny?

If you share the same sense of humor, things are going well.

Humor is something that unites us with other people.

Think about it. You’ll probably end up laughing a lot with your best friends every time you spend time with them.

That’s part of the reason you’re friends.

Therefore, the fact that you and your date find the same things funny may be a reason to consider continuing to meet.

6. Are you a morning or a night person?

People have different sleep schedules: some wake up early in the morning, while others stay awake until early in the morning.

Asking this question to your date will give you insight into her daily habits.

For example, do they get up early? to go to the gym or binge-watch their favorite shows at night?

This can help you know whether or not you are compatible.

7. If you could spend an afternoon with anyone, living or dead, who would it be?

This question allows her to tell you about someone she admires.

Maybe her grandfather whom you never met or maybe a celebrity or an activist.

It doesn’t matter much what she says, however, it will allow you to start a conversation.

8. If they made a movie about your life, who do you want to act as you in the movie?

This question gives you a measure of the size of her ego, and the actor or actress she chooses will give you clues about how she views herself.

9. What do you value most in a friendship?

This question reveals what kind of person she is.

Do you value honesty, integrity, humor, partying, or something else?

It also gives you an idea of whether or not you would feel good with her, an aspect that could be very important in the future.

10. What is the most intriguing fact you are aware of?

People know a lot of interesting things.

This is a fun question to find out what an older woman knows, and you might even learn something new.”

Plus, we all love to look interesting. It’s great that you allow her to do so.

11. What is your greatest achievement?

This allows her to show off.

It will also give you an idea of how hard she is willing to work to get whatever she wants.

12. Who did you see at your first concert?

Music is a great topic for a date.

Prepare to be shocked that the first artist she saw was Beyoncé, or amazed that she saw Nickelback.

13. What is your most precious memory?

First of all, talking about her most precious memory will put her in a good mood.

But it will also give you information about what she values most, whether it’s family, friends, work, or anything else.

14. When was your best day ever?

This question will take her back in time to a great moment in her life that she’ll love to remember.

This turns the conversation into something much deeper, and it will make you stand out from other men she has gone on dates with.

15. What is your favorite holiday?

This question can give you insight into her religion based on her answer, which can become an important part of the relationship.

It can also open up a conversation about religion, which while it may be too strong for a first date, it also might not be.

You will have to calibrate it yourself to see if you should take the conversation there or not.

16. What is the best gift you have ever given someone?

She will try to show off a little while feeling very generous.

It’s also a big red flag if you find out that she has never given anyone a gift.

17. What do you like most about your job/career?

This question allows you to talk about work positively, rather than boringly asking, ‘So, what do you do?’

18. What were you like as a girl?

Sharing childhood stories gives her a chance to be vulnerable by letting her open up about her younger self.

You’re helping her connect with you and her younger self.

19. What is your favorite food?

Who doesn’t like food?

This question will allow you to find out what kind of food you have in common and, if things go well, it can even help you decide where to go on your second date.

20. What is your hidden talent?

This question will allow her to show off while sharing a secret, and sharing personal secrets often builds trust and connection.

21. What would you prefer…?

The first date should be fun, and the ‘Would you rather?’ questions should be fun too.

They have a lot of comedic potential.

A 2014 study found that women are attracted to men with a sense of humor.

Some fun examples could be:

“Would you prefer engaging in a snowball fight or a food fight?”

“Would you rather accidentally walk in on your parents having sex, or have them unexpectedly walk in on you in that situation?”

“Would you rather be a Cyclops or have eight arms?”

22. What do you usually do on weekends?

This question allows you to see if you have compatible lifestyles.

If her weekends consist of reading in bed while most weekends you are at a club drinking with friends, she may not be the right person for you.

If you have similar weekends, then the conversation will flow naturally from there.

For example, if you both like to read, you can talk about your favorite books.

If you both like to go out, you can talk about your favorite bars.

23. What’s on your wishlist?

This question not only gives you an idea of her interests but also gives you great ideas for date number two.

24. Do you want to share an embarrassing moment?

On dates, we try to present the best version of ourselves, but sometimes it can all get a little too serious and even start to sound a little “snooty.”

This question helps you and your partner be vulnerable with each other, breaking down any facade.

The Worst Questions to Ask an Older Woman

Here are questions you shouldn’t ask an older woman:

1. Why are you single?

Although this question may seem harmless, it will make her feel uncomfortable and unsure how to respond.

It can also be read as an insult. In simpler terms, you’re asking, “What’s wrong with you?”

2. How many exes do you have?

Asking such a personal question on a first date can be a big red flag.

It’s important to keep her privacy in mind and not ask anything that might make her feel uncomfortable.

3. How much money do you earn?

Someone’s income is not an important piece of information for a first date and can make you seem like you’re more interested in the money than the real person.

Ask questions that allow you to learn more about her heart, not her money.

Conclusion

Act like a grown-up, not a kid, if you want to impress an older woman.

Older women want a partner, not someone they have to take care of like a child.

If you act immature, she’ll probably reject you and might even become dominant in the relationship, which isn’t ideal.

So, be mature to make a better impression.