Mature Dating 101: 5 Things to Say, 5 Things NOT to Say, and 5 Red Flags to Watch For!

Romance, love, friendship, fun, sex, caring, and commitment are part of most people’s core life experiences. As we look back over the decades, our relationships make up the lion’s share of our meaningful preoccupations. If you are over 65 and single, you might be exploring intimacy again. You are never too old to light the fire of passion and belong in a loving romantic relationship or a close friendship.

Here are some sobering statistics from the Senior List: Among people aged 65 and older, 49% of women report being single, compared to only 21% of men. So, ladies, there may be more women available for socializing than men. Also in 2023, over a third of adults of both sexes between the ages of 50 and 80 reported feeling socially isolated in 2022. It is high time to reach out and get to know people!
In this article, we suggest five things that are GOOD to say on first dates, five things NOT to bring up, and five “red flags” behavior that might undermine your initial date.

5 Good Things to AskDo You Like Pets?

This is a real ice-breaker. You can learn so much about a person on the topic of pets! They might love and care for their animal companion(s). They might have an exotic pet, snake, bat, or spider! They might have no pets at all, as their lifestyle makes it awkward, but cherish great memories of them. Your date will likely light up telling you about their experiences with animals! And you will have your stories to tell too.

Where Do You Like to Dine Out?

You could happily chat for ages about your preferred eateries and experiences there. If you live in the same area, you might both go to the same places. You will learn something about the food habits of your date in this conversation. Maybe you are both vegetarian, vegan, or pescatarian. Or both rabidly carnivorous! Or even dieting. This topic is very personal but also represents neutral ground. By talking about food, you will get to know your date better. Everyone likes to eat, right?

Can You Remember Where You Were, When…?

Another good first date topic is, “Where were you when…?” Depending on your age and interests, you might ask about upbeat events, like the 1969 moon landing (when very young), the 1985 LIVE Aid concert, the 1989 fall of the Berlin Wall… These world events tend to unite us, and your date will be keen to share their memories and so will you! The trips down memory lane will bring you together in good spirits and give you insights about each other.

What Are Your Parents Like?

Talking about this topic will give you a feel for your date’s personality, family of origin, and adult family life. But on a first date, probably in a broad, general way! If they have lost their parents, or they are still alive, you will learn a lot. And the fun side of family life can be shared! Plus it will lead to sharing their expectations of new family relationships. You will get a glimpse of them when young, as an adult, and in their present stage. Be prepared to share your own story!

When Were You First in Love?

This topic might seem very (blushingly) personal for some, but the stories of first loves will be interesting and will give you insight into your date’s “heart history.” Asking this question cuts to the chase, giving you a ringside seat to your date’s romantic tendencies and life story. Let’s be honest, you are both exploring the possibility of love and attachment between each other. You are never too old to fall in love, believe in love, or act on your feelings of romantic love or even platonic friendship (if the chemistry just isn’t there but you really like them).

5 Things to Avoid AskingWhat Are Your Political Views?

Straying into no man’s land sharing political views is maybe not such a great idea on initial dates. In 2024 with wars, pandemics, challenging economies, and climate change, this topic is not much fun, nor is it heartwarming. You both might express your political passions without knowing if you are aligned, and this may raise doubts about your compatibility. It is of course possible to love and respect people with alternative views, but if you get on a soapbox, it is a surefire way of killing any budding romantic, tender feelings!

Do You Have a Good Retirement Plan?

You might not ask a question quite as directly as this, but any query about their home ownership, salary, or retirement security plans is not what an initial date is all about! You want to get to know them as a person and sure, finances are very important, but money talk might cloud your judgment. If you and your date get along and things are exciting and happy, the money discussion will inevitably take place further into your relationship. People are sensitive about this topic, and it is ultimately not relevant to a love match.

What Was Your Last Partner Like?

Sure, you will be curious about your date’s romantic history. If you start to really get to know them this topic will be on the table, but in the initial stages, it is not so appropriate to be too nosy. To a certain extent, it may be difficult and awkward for your date to talk about relationships that are over. The stories of past loves will be told if and when they come naturally. First dates are better times to concentrate in a lighthearted way on each of you as individuals.

How is Your Health?

This question, however well-meaning, is a bit personal for first dates and again, is a topic that will unfold as you get to know each other better. Most people in their maturity have at least one medical condition they are managing. There is often stigma surrounding certain conditions, and you and your date will have a better time if health matters are not a focus, as you enjoy more carefree interaction.

So, What Do You Think About Us?

If you are the type that likes to be reassured by your romantic partners, it might cross your mind to ask this question as your first date ends. Be wise and don’t ask! It is too early to get a response! You will find your answers in your date’s body language, expressions, tone of voice, and perhaps the suggestion of meeting again (or no mention). All in good time. Be content with a follow-up message after you have parted company, suggesting another date (or saying thanks, but no thanks). You are not at the mercy of what others think! You will know when things are good between you and your date.

5 Red FlagsThey Flatter You or Give You a Pet Name Quickly

It might be flattering to be repeatedly called “gorgeous,” “handsome,” or “sweetheart” on your first date, but it might be a habit of your date to call people pet names, and you may not be the only one they use such terms of endearment with. Also, it is a bit insincere when you hardly know each other. Loving pet names usually come with a more established intimacy.

They Treat Wait Staff Disrespectfully

You can tell a lot about a person’s general personal standards by how they treat other people. On your date, you will see how they treat waiting staff, and if they are off-hand or disrespectful, you will notice. They may be oozing charm for you and less concerned about kindness for others.

They Speak Ill of Their Exes

If your date dumps a whole load of negativity about their exes, it will leave a bad impression and make you wonder what they contributed to the break-up. Like job interviews, it is not good form to openly criticize your former partners in the first meeting with a potential new one.

They Suggest Last-Minute or Late-Night Plans

First date plans tell you a lot about the person. Last-minute plans, catching you quite unprepared, are a bit pushy and thoughtless. Late-night plans are also not so appropriate and give the impression of someone very busy during the prime time of the day and night. Maybe they want to fit you in or go home with you pretty quickly!

They Get Physical or Touch You Immediately

It is a red flag for women, especially, if their date ignores personal space boundaries and touches them on an initial date. It could be an innocent flirtatious touch or even more controlling physical contact; but touch of whatever kind may raise suspicions and perhaps lead away from more dates with them.

Posted by Maya Chen