What Questions Should You Ask an Older Woman?

Whether you’re sending those first few messages to initiate contact, preparing for an exciting first date, or getting to know someone better, you need to arm yourself with some probing, thought-provoking questions. This is especially important if you’re dating an older woman. If you can get her talking, she’ll open up, you’ll learn more about her, and you’ll both feel more at ease. So, let’s look at some of the best questions to ask an older woman!

Questions about Hobbies and Interests

Regardless of the age of your date, the following questions should help to break the ice and give you some basic information on the expectations of older women. But remember, you’re not interviewing them. You do want to learn their story, their likes, their dislikes, but this is a conversation. It’s a conversation. Listen to what they have to say, probe further with additional questions, and add some insights and opinions of your own.

Here are some examples of simple, icebreaker questions and how you can follow up:

•   What are your favorite hobbies?

o Learn about her hobbies. What does she care about and enjoy? Express an interest, and reciprocate with your own experiences if you have any similar passions.

•   What do you do for fun?

o You could learn that you’re complete opposites, and that’s good to know, but there’s always something you can relate to. If not, it’s still a great way to discover her passions and help you plan future dates.

•   How would you spend your perfect weekend?

o Who knows, if things go well, you could plan her perfect weekend for a future date.

•   What’s the best trip you’ve ever taken?

o Let her tell the story in full, show an interest, and follow it with your own.

•   If you could go anywhere in the world, where would you go?

o You can learn a lot from this question. Does she prefer sunshine and relaxation? Busy city breaks? Adventure vacations? You’re asking whether she is introverted or extroverted, adventurous or shy, without actually asking.

•   What book or film changed your life?

o If you’ve read/seen it, perfect! If not, take her recommendation and make an effort to read/watch before your next date. All adults have that key thing that influenced them, and for many senior women, there could be a number of life-changing books and films to discuss.

•   What’s the most embarrassing thing that has ever happened to you?

o The ice will definitely be broken at the end of this story. If she is reluctant, offer to begin with your own story but keep it short, and if you’ve just met her, don’t reveal too many embarrassing details.

•   What’s the most unusual thing that’s happened to you?

o Their answer might be a little odd, but it’s a chance to show that you’re a good listener and can empathize. If they’re used to people thinking they’re weird or odd when they tell this story, being the person who acts sympathetically should put you in her good books.

•   What is your favorite website?

o Asking her about her favorite website can tell you a lot about how tech savvy she is, as well as how she uses the internet. Does she spend her time browsing for bargain products and services or does she chat and play games? Does she use any sites strictly for adults or simply see the internet as a nuisance?

Ask about Her Career and Ambitions

Women over 50 know what they want from life, and they may already be well on their way to achieving it. They may have spent years working toward their goals and are usually keen to talk about their efforts. So, these questions will push the conversation beyond typical icebreakers and small talk and into something more revealing:

•   What inspired you to choose your current career path?

o It’s not only a great way to get some insights, but it’s also a good question if you forgot what she does for a living or couldn’t get enough information from her profile or previous messages.

•   How do you balance your professional ambitions with your personal life?

o An ideal question to ask an older lady, as she probably has a good hold on things and has had enough experience to strike a balance between family, friends, hobbies, and work. If that balance isn’t there, it could be a cause of frustration for her, allowing you to lend a sympathetic ear.

•   Are there any professional goals you’re currently working towards?

o Encourage, show interest, and express your own goals. If they align—perfect!

•   What are you most passionate about in your work?

o Even people who dislike their job have something they enjoy about it—focus on that.

•   What are your biggest career goals for the next 5 years?

o Whether she’s ambitious or not, she’ll have goals. Most women are happy to share them, and you can learn a lot from them.

•   Have you ever taken a big professional risk? What was the outcome?

o One of the best questions to ask a mature woman, as you can use it as a learning moment, and everyone is happy when they feel like their experiences have helped to teach others.

•   What inspired you to choose your current career path?

o You can get some useful insights into her personality, whether she went into senior care because she loves to help others or took a job in a bank because she has a head for numbers.

Ask about Life Experiences

Every relationship, job, tragedy, and celebration—it’s experience, and that experience is one of the best things about getting older. We have more to look back on, more to share, and more to teach us about life and the world around us. So, probe into her experiences and encourage her to open up:

•   What’s one of your favorite memories from your travels or adventures?

o Was it a restaurant, a hike, or a good time with family and friends? Is it a nostalgic experience from when they were a young girl (something you can recreate to win favor) or something recent?

•   Can you tell me about a time you took a big risk and how it turned out?

o We’ve all been there, and while those risks don’t always work out, sometimes they change our lives for the better. It could be related to health or difficulties in the relationship, in which case you may want to step back to avoid getting too personal, but you can let her lead.

•   Who has been the most influential person in your life, and why?

o Was it a friend, family member, teacher? Who does she take inspiration from, and what can that tell you about her personality?

•   What traditions or customs are most important to you?

o It could be attending church every week, going on a certain vacation every year, or even following a specific routine at Christmas. Share your own in reply.

Ask about Hobbies and Interests

Learning how they spend their free time is not just a great way to discover more about them, but it can help you plan future dates and find something that you both enjoy.

•   What hobbies have you picked up that you think everyone should try at least once?

o Express an interest and actually follow through. She will be impressed if you show up to your next date having tried her hobby.

•   Do you have a particular hobby or activity that helps you relax or de-tress?

o Regardless of age, there’s always something that people do to relax and unwind. She might like watching films, browsing a certain website, reading books, playing golf, coaching kids, or even abseiling—it’s important to her, so show an interest.

•   How do you typically spend your free time, and are there new activities you want to explore?

o You can do them together!

•   What’s your go-to activity for a fun day out?

o Next date, maybe?

Questions about Family and Relationships

You don’t want to dig too deep into family and relationships if you’re only just getting to know one another, but these are great things to ask once the ice is broken.

•   What has been your most important lesson learned from family life?

o How a person learns from their mistakes and life lessons can tell you a lot about them.

•   How do you like to spend time with your family or close friends?

o You could even get an invite! That’s always a step in the right direction.

•   Are there family traditions that you hold dear or look forward to each year?

o Getting to know her family and the people that care about her is an important step in any relationship, so it helps to know more about family and traditions, as well as the aspects of her family life that she doesn’t like.

•   How has your relationship with your family influenced the person you are today?

o Is she close with her family, or has she distanced herself following bad experiences? How do her experiences relate to your own?

•   What roles do love and friendship play in your life?

o Is she open and ready for love or a little emotionally closed off following a bad relationship?

Flirty Questions to Ask an Older Woman

Everyone loves to flirt! It shows your playful side, breaks the ice, and opens the door to so much more! So, whether you’ve just started dating or have been going at it for a few weeks, spice it up with some flirty questions every now and then. To get you started, here are some to ask an older woman:

Advice for Having a Conversation with Older Women

A question isn’t a conversation, but it can lead to one. So, rather than writing all of the above down and then using them one by one in quick succession, keep the following in mind:

Practice active listening

What was that? She’s smiling at me, but she’s silent. Did she ask me something?

If this sounds like what’s going through your mind during those dating conversations, you’re not listening enough. No one wants to feel like they’re talking to a brick wall, so listen, and make sure they know you’re listening. Nod. Change facial expressions to match what she’s saying. Encourage her to say more. Offer opinions if she asks for them. It shows that you’re listening, and that can make a huge difference to the opinion she forms of you.

Ask further questions

She answered your question, and now you’ve moved onto another one. But she seems distracted, perturbed. It’s probably because you changed the topic too soon, showing that you aren’t really interested in what she says, and simply want to get through your preplanned list.

Let’s take one of the above as an example: “What are your favorite hobbies?”. She answers by telling you she loves to read. She doesn’t really have much time for anything else these days, but reading helps to relax her.

Now’s your chance to push her further. Ask her what types of books she reads. Does she like comedy, non-fiction, horror, romance? Who is her favorite author? What’s her favorite book? As long as you’re showing an interest, she’ll be glad to open up, at which point you can ask for recommendations or discuss books you have read in that genre or from that author.

If you’re not big on reading novels, talk about your love of non-fiction or magazines, and if that doesn’t fit, mention the movies you love—some could be based on the books she likes. Failing that, make a joke of the fact that the only thing you’ve read lately is the back of a shampoo bottle. It might be a dealbreaker for her, but she’ll appreciate your honesty. At least you’re not pretending to like something just because she does. You’ll have other things in common, so just take the hit and keep going.

Pay attention to her signals

She might not be comfortable with certain lines of conversation. If so, she’ll probably be brief and dismissive with her answers. When that happens, shift the conversation to something she’s happy to discuss. Don’t push and probe when she’s clearly not happy with the topic. You can find out why at a later date, but in the early stages of a relationship, there will be barriers that she’s not willing to pull down.

Summary: What to ask Older Women?

The questions you ask an older woman aren’t that much different from the ones you ask women of any other age. It’s all about igniting a conversation, getting to know more about them, and making sure you’re both comfortable with one another.

Just remember, it’s not a job interview. You’re also part of the conversation, and if you want to make them comfortable, you need to show that you’re listening and respond to their messages with personal insights, opinions, and further questions. If you get this aspect right, everything that follows will feel natural and comfortable, and you won’t need more. If not, go back to step one, ask more questions, and pay attention to how she responds.

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