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Mature Dating Tips: 5 First Date Questions… and 5 Topics to Avoid!

By Lisa Copeland December 02, 2022 Dating

I believe that first dates are meant to be light and airy as you spend time getting to know someone. Most women in their 50s and 60s don’t realize they have choices they didn’t have in their 20s as to how a man can fit in their life.

Men can be your lover, your friend, your boyfriend, your companion, your friend with benefits, your husband, or nothing. You get to decide.

These choices give you the luxury of taking some time to discover a man’s personality without having to quickly assess him by using what I call The Dating Resume Questions.

These are questions that you fire off one after the other like: How many kids do you have? What do you do? What type of relationship are you looking for? How many times have you been married?

Questions like these make a man feel like he’s on an interview, and they put you both on edge as you try to make decisions before a cup of coffee is finished.

Now that you understand you have choice on your side, try using these 5 soft questions to find out more about a man’s life. These questions can be far more revealing, and they can make your date far more fun and interesting as you spark good conversations that help create a connection between the two of you.

5 Things to Ask on a First Date in Your 50s

What’s Your Favorite TV Show?

With so much to watch on Netflix and Amazon Prime, asking about their favorite TV show can create hours of good conversation.

Do You Have a Pet?

If you have a pet, you want someone who will appreciate your baby, and that’s why this question is a good one for weeding out men who are allergic to animals or don’t like cats or dogs – or reptiles!

Are You a Morning Person or a Night Owl?

You should also find out your time preference compatibility, especially for the times you are on vacation. You don’t want to be looking at a romantic moon by yourself every night on the balcony of a cruise ship because he’s gone to bed at 9 p.m.

Where Were You for This Significant Event?

Significant events make an impact on our lives, and we can usually remember where we were when they happened.

Examples of these are: Where were you when you heard President Kennedy had been shot? Or where were you when you first heard the Beatles? Or what was your favorite band at Woodstock? Looking back, would you have gone? Sharing history can create a strong connection.

What’s Your Favorite Restaurant?

Sharing your restaurant favorites is a great set up for future dates. He’ll have an idea where you like to go, so he can be successful at planning a future date. This question will also reveal whether your food tastes are compatible. If you’re a vegan and he’s a major meat eater, this could be a problem.

5 Questions You Don’t Want to Ask a Man On a First Date

What Are Your Political Views?

In the past, I would have said absolutely don’t bring up politics on a first date. But, in today’s very divided world, I think it’s important to get an idea of where someone stands on issues that are important to you.

Now that being said, it should not be the first thing you ask about. Sometimes, as you get to know someone, you’re better able to tolerate differences than you are on a first date. If this topic is a deal breaker for you, then mention it in your profile.

Where Do You See Us Going?

Ok, so you like the guy and maybe he likes you, but you want to remember you’re on a date not in a relationship. You come across as super needy and desperate when you breach the “future” topic on the first date.

Why Did Your Last Relationship End?

Of course you’re curious about the guy’s previous relationship, but unless he brings it up, leave this question for when you really get to know him. It may have been a bad breakup, and bringing it up before he is ready to share can really sour a 1st date.

Do You Have a Retirement Fund?

I know you want to get some idea as to whether a man can support himself, but asking after his finances should be left for when you’re ready to explore creating a relationship. As you get to know him, note where he takes you. It will give you an idea about his lifestyle.

Do You Own Your House or Rent?

As with the previous question, you may be trying to assess if a man is financially sound but now’s not the time.

The only purpose of a first date is to have fun meeting someone new and interesting so you can decide if you want a second date if he asks. Let the conversation flow with questions that connect you. This is what creates an attraction and can lead to the long term relationship you’re looking for.

Let’s Have a Conversation:

What questions do you usually ask on a first date? What questions do you get asked? Which topics tend to sour the mood? When do you have the most fun on a first date? Please share your experiences with our community!

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Lori Rudiger

One of the most important compatibility questions during the very early dating phase but difficult to execute: What is the general sexual compatibility with the person you have started to date? Not specifics yet, but to be interested in someone and start to invest and then find out a month or more into the dating courtship how far apart you are(if you havent been physically intimate yet) not only can hurt the heart but also the time invested. There will always be differences in your intimacy desires, needs and bounderies, but respectful and real communication is key to know early on if you are “10 yards or 100 yards apart out the gate”.

Ardith T

I like these questions! I might also ask them to describe a trip they enjoyed taking.


I agree with all your topics you say should be off limits – except for one. If a person is a trump supporter – that is a moral issue for me and it absolute deal breaker…

Lisa Stege

I look for a more or less even exchange of sharing the conversation. No matter what someone is talking about, make sure that you listen, and don’t just wait for your turn to comment. A red flag for me has been when someone constantly interrupts to turn the subject being discussed back to themselves. A recent date was a textbook narcissist.

The Author

Lisa Copeland is a leading internationally recognized Love Coach and Dating Expert for women over 50 inspiring and teaching them how to feel confident, empowered and joyful dating. You can get a free copy of her eBook “The 5 Little Known Secrets to Finding a Quality Man” at

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