7 First Date Questions for Mature Daters Over 40


Questions about dating after 40

By Top10BestDatingSites Staff

Dating in your 40’s can be a challenging experience. Most likely, you’ve recently come out of a long-term relationship and dating is not something you’ve done in a long time. It’s not like you're fresh out of college, you know that your life experiences and your date's life experiences are likely to mesh up in many ways. At an older age, when you've both lived full, exciting lives, it can be a little harder to find some common ground and first date questions can be pretty difficult to navigate As general dating advice for men and women over 40, it's a good idea to ask open-ended questions that allow your date to really describe their lives and their opinions. To help you break the ice, we’ve created a few questions that you can definitely ask on your first date to get the conversation going. 

1. What is Your Average Day Like?

One of the most thrilling things about dating as a mature individual is that your date is likely to have a life completely different than your own. Asking about their day gives you a better understanding of who they are - but it also tells you some important things, like their priorities, routines and schedule. When will you be able to see them? How often? Is their day already jam-packed, or does it sound like they live a life of relative leisure? This information can reveal a lot about your date and let you better understand if you want to be a part of their average day or not.

2. What Are You Most Passionate About in Your Life?

Early in life, we tend to be most passionate about our careers. But later in life, we grow in other areas - interests, hobbies and family. Your date's passions will tell you a lot about the future that you could have together. Are they most passionate about solo activities? Do they love hanging out with their family? Are they still a workaholic? All of these things will set the tone for your future relationship.

3. What Are You Looking For in a Relationship?

While this question is great regardless of age, mature daters are the ones who can answer the question with confidence -- or, at least, should be able to. When you ask this question in your 20s, you're going to get back a lot of guesswork. When you ask this question in your 40s (and beyond), your date should be able to give a thoughtful, specific answer based on a lot of relationship experience and knowledge. If you're a mature dater and your date can't answer this question – it’s a warning a sign. If they don't know by now, you probably shouldn’t be their practice run. 

first date: dating advice for men over 40

4. If You Could Do Anything You Wanted, What Would You Be Doing Right Now? 

We all have dreams. Sometimes we get quite close to them -- other times they always seem to evade us. But dreams don't just tell you what a person values, they also tell you how satisfied they are with their current life. Is your date going to end up quitting their job to summit Mount Everest? Probably not. But if they're not satisfied in their current lives, it could be a warning sign of things to come.

5. Do You Have Any Interesting Travel Stories?

Travel tells you a lot about a person. If you have the travel bug yourself, it'll be fascinating to hear about all of the exciting experiences that your date has had. And it'll give you a better indication of how they react to problem solving and things going awry. Are their travel stories about the things that went wrong about a trip, or the things that went right? You can find out a lot about your date’s personality and character from these stories, and they are a great topic to talk about.

6. Do You Have Kids? Tell Me About Them

Like it or not, your date's children are inevitably going to be a part of your life when dating after 40 -- don't just assume that because they're adults and out of the house that you'll never see them. In today's economy, many adult children still live with their parents, which is something you don't want to be blindsided by. And, if you're dating in your early 40s (or even mid-40s!), don't just make the assumption that they're "done" with kids or that they don't want to have children. A lot of people are successfully adopting late in life! This question also opens the door to talk about any prior entanglements. Many mature daters are divorced or even just separated. If they have kids with an ex-spouse, their ex-spouse is probably still a part of their life. A bit of dating advice for divorced men and women: being upfront of about it is always best. 

7. What Do You Want to Do When You Retire?

This question is as much about personality as it is about responsibility -- it's a great way to launch an animated conversation. Does your date have a financial plan? It's not something you can ask directly during a first date, but it's still important. Sneaking this one in gives you information about their values and goals, and it also tells you exactly how well prepared they are for the future. If they just laugh it off, you know to be a little cautious. As dating advice for men and women over 40 will often caution, financial issues can play a significant role in mature dating. The most important thing to remember is to just listen and be yourself. Even just talking about the daily news will give you interesting insight into your date's thoughts and opinions.

The most important thing to remember is to just listen and be yourself. Even just talking about the daily news will give you interesting insight into your date's thoughts and opinions. Don’t be afraid to express your opinions and beliefs. If your date is interested to listen and ask further questions, then they are certainly intrigued.

Remember, before you can ask those all-important first date questions, you need to actually get a date! There are many dating sites available today specifically for mature ​daters who want to put themselves out there and get active on the dating scene again. So what are you waiting for?

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