The First Date
~ as a senior citizen ~

The first date.

The first date, after not having dated for 20, 30, or 40 years can be very nerve wracking.

“Breaking the ice” is usually the hardest thing for us to do.

What are the best first date questions for seniors to ask each other?

(And, what are the question that can cause a disastrous first date?)


The first date Senior Survey.

We sent a survey to 211 single senior citizens asking them “What Would Make The First Date for Seniors a Good Date?”.

SURPRISINGLY we got 186 replies! That’s whopping 88%! That’s the highest response rate we have ever gotten from any survey so far.

That tells us there are a LOT of single senior citizens who would enjoy meeting someone new. Whether for dating and romance, or just a good new friend to talk, do things with, or,  just spend enjoyable time with.

Since this article is about making the first date a wonderful experience, we’re going to show you how easy that can be.

Asking the right “First Date Questions”, with a good attitude is all it takes.

So, in the Survey we wanted to find out two main things:

     #1)  What questions do seniors enjoy? The ones that get them involved and engaged with each other on a first date.

     #2)  What questions do they hate having to answer? The ones that make them cringe and just want to run away.

In a moment we’re going to give you the answers to both of those.

First, we found this very interesting:

What Do Senior Women and Men Want Most
First Date?

One of the things we asked on the survey was: “What would you like to have happen most on the first date?”


“I want to have an enjoyable no pressure evening with good conversation with a nice man.”


“I’d like to be with a woman who is easy to talk to.”

What seniors want most on the first date.

It seems like women and men both want the same thing. So, you can relax! There are no great demands here.

But, how do we get that conversation going?

By asking the right questions. And, we're going to be giving you a whole bunch of the very best ones!

How Long Has it Been
Since You Went Out On a Date?

Seniors, how long has it been since you've dated?

You got a date this weekend. You’ve found a great place to go. Casual, yet fun. Perfect!

BUT: After 30, 40, or 50 years of not dating, what do you talk about on a first date? You’re nervous.

And, that’s OK. In fact, that’s normal.

You’re definitely going to be out of practice! In fact you’re most likely going to be as nervous as a deer unable to move from the middle of the road, staring at the head lights of an approaching car.

Don’t worry. We’re going to get you past that uncertainty right now.

We’re going to show you how to make that date a great success. Easy, and FUN.

The 2 Most Important
Things to Remember

The two most important things to remember on tfirst date.

Fortunately, as seniors, starting to date again at 50, 60, or even 70 and 80 is not as difficult as it may feel to you right at this moment. Really.

In fact it’s easy and fun if you have an idea of how to talk comfortably with your partner.

The 2 most important things to remember on the first date are:

#1)  Have a “normal” conversation. Make it as fun as possible. Don’t get all kinds of serious. Ask the right questions to get one going. And, above all: Don’t ask the boring, or overly personal, questions that will kill any chance of making a real connection. (we're going to show you what those are...)

Have you done that already? Mess up terribly? Kicked yourself all the way home?

Don’t worry. You’ll get another chance. Even many more chances if you need them. That date wasn’t the last chance you’ll ever have to meet someone new.

#2)  Be truly interested in the other person and what they have to say.

Let’s Clean House…

That’s means: Let’s get rid of all the things we could say to mess up a first date.

So, before we get into the right questions to ask, let’s “clean house” a little and get ALL the wrong stuff out of the way. All the wrong questions that can sabotage your hopes and dreams.

As seniors, we know a lot more about what we want in a partner, or, even a new friend. Right? But, the first date is NOT the place to find out this information. So, let's take a look at questions (that we may need answers to later) that we really don't want to ask on a first date.


Here we go:

Avoid These Topics and Questions
if You Want The First Date to Go Well

General Topics to Avoid:

  • DON’T  speak about your ex

  • DON'T  talk about any family dramas

  • DON'T  complain about anything. I mean anything. If you don’t like something, smile, and be silent. Pick another subject

  • DON'T  talk about any medical issues you may have, recent surgeries, or any illnesses

  • DON'T  discuss finances, income, or money

  • Religion and politics, never a good choice

  • Sexual history is also an area to stay completely away from

Specific Questions to Avoid Like the Plague
on the First Date:

Don't ask these questions on the first date.

Not a single one of these questions is going to make the other person feel good. And, feel you are a great date. Each one will reduce your chance of a second date. So, get familiar with them, AND, never ask them:

"How old are you?"

"Do you wish you'd had kids?"

"Why are you still single?"

"Do you worry about dying?"

"Did you have a color TV growing up?"

"How much money do you make?"

"Can you still do that at your age?"

"Do you know how to use email?”

"Do you wish you'd been more successful?"

"Have you had plastic surgery?"

"Do you wish you'd gotten married?"

"Are you tired?"

“What did you really want to do with your life?”

Seriously.... would you want anyone asking you these things on the first date? Right? Geeze!...

Want to
 Make Things Even Worse on The First Date?
then try these:

One of the worst questions for the first date.

What are your political views?

The kiss of death. Having the same views is great. Having opposing views? You might as well just say “goodnight”.

"Do you have to diet all the time?”

Many women have life long weight problems. They worry about it almost daily. They are finally on a date with a seemingly “nice man” and what do you do? Ask about their weight. Their diet. Their fat. WRONG question.

"When did you lose your hair?”

Women with weight problems and men who have lost their hair are in the exact same self conscious place. No guy wants to be bald. No guy wants you to pay any attention to it. On this you can trust ME. I lost my hair at 22. Young! We don’t like talking about it! We just want you to like us and think we are OK as we are.

"Do you wish you'd done more with your life?”

OMG. You might as well say, “You’re such a loser. Do you wish you tried harder? Or, are you just incapable?” Forget a second date after that question…

"Are you having a senior moment?”

This is no way to score points with someone who is on their best behavior and trying to look and be their best for you.

"When did you go gray?”

Or maybe: When did you start looking old? When did you first realize your most beautiful days are gone? When did you realize you’re no longer as attractive or young as you once were….. Better to just walk away and hide under a rock.

"Have any of your friends died yet?”

Oh, yes. A favorite date killer. Talking about death on a first date, especially that of friends, is a real crowd pleaser.

"Who's getting that when you die?”

Oh, yes, remind your date that there are not many shopping days left until Christmas. They are close to the end of the road. The last hurrah….. Always a great energizer and uplifting thing to do.

"Are those your real teeth?”

Oh, you really are falling apart aren’t you? No teeth? Geeze. I had no idea. No teeth, huh? For how long? Wow. Well those look real nice. Is it hard to chew?…. Instead: Why not just tell them you personally are an idiot, have no social grace, and that they should  just walk away now and never speak to you again.

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 the first date not in a relationship. You come across as super needy and desperate when you breach the “future” topic on the first date. This applies to man or woman.

Why Did Your Last Relationship End?

Nothing like bringing up an unhappy memory (that is none of your business anyway) for someone to get them real enthusiastic to see you again. What if they were in love with their last partner and the person just walked out on them. Or died. Traumatic! Maybe next time, if you try a little harder,  you can really bum them out. Even make them cry. Oh, yes! Can’t wait. Great first date material….

Do You Own Your House or Rent?

None of your business on the first date. Don’t talk about their dwelling unless they bring up the subject. And then still: Don’t ask if they own it. It’s their home. Own or rent. Instead, ask about how they decorate it. What their favorite room is. etc…

Do You Have a Retirement Fund?

Or, maybe: “Tell me how much money you have put aside.” Or, just tell them very directly you’re hoping they have lots of money put away because you’re a high maintenance gold digger, or, a you're a lazy blood sucking male who has always needed support. And, of course, you want to be kept style.

Those are our all time best selections for how to ruin the first date in under 15 minutes!

How to Choose
GOOD Questions for The First Date

We hope you got a laugh or two from that last section. But, seriously, don’t ever ask any of those questions on the first date.

OK. So we just got rid of all the things NOT to ask. A lot! Right?

Making the first date for seniors a HUGE success!It's a FIRST date. So, just relax and have fun!

Remember: It’s a first date. You both want to relax and have fun. Stay on pleasant, fun and funny topics. Have FUN. See the beauty in your date.

The question itself is often not something you really need to know the answer to. So, just flow with whatever answer you get (Unless it’s a tragedy. Then be silent for a moment and gracefully pick a new subject).

You don’t really need a persons history now. You just want to get an easy conversation started. One that makes the other person comfortable. A conversation that becomes fun for both of you.

Be truly interested in the other person. That, and kindness, are the most important things you can have on a first date.

It's Easy to Start a Good Conversation
With the Right Questions

The first date. Question to get a good conversation going.

This one is always a good first question:

How has your week been so far?

This is a favorite because it leaves the person so much room to talk about anything they want.
 This one is also a real winner because the other person gets to talk about themselves, and things they can remember well, and some things they like. Or, hate. Who cares? It gets them talking easily. And, it shows that you are interested in them. And, you’re not centered around yourself.

Pay attention to, and be truly interested I’m them and what they are saying. If they bring up something you can get interested in, ask more about it.

On The Other Hand: If you talk about yourself a lot (without being asked), you’ll never see a second date.

Even if you talk about yourself too much when asked, you’re also out of the water. No one enjoys a pompous ass. And, even if you’re a wonderful charming caring person (which you probably are!) and you talk about yourself too much because you’re just nervous, you’ll come off as self absorbed.

After you answer a question comfortably,  ALWAYS try to direct the conversation back to your interest in the other person.

This goes for both men and women.

If both of you are doing this, you can’t help but have a very enjoyable and interesting conversation.

Here’s more:

  • What does an ideal weekend look like to you?

  • What is your favorite childhood memory?

  • If you could recommend one book to me, which one would it be?

  • Do you enjoy your work?

  • Where did you go on your last holiday?

  • What’s your guilty pleasure?

  • What do you enjoy to do in your free time?

  • Where are you from originally?

These Are Some of The
Favorites from Our Survey:

Favorite question for the first date as seniors.

We asked our surveyed seniors, "What is a question, which was easy to answer, that you enjoyed being asked on the first date?"

Here are some of the answers:

  • What makes you laugh the most?

  • What is your biggest passion right now?

  • Tell me about your family.

  • What was the most fun job you ever had?

  • Do you have a bucket list? What's on it?

  • Do you have siblings?

  • Do you enjoy cooking?

  • Are you a pet person?

  • Do you have children? Do you have pictures? Tell me about them.

  • Are there any dreams you are currently pursuing?

What is a Question
You Enjoy Being Asked?

The first date: What makes you laugh the most.

We asked our surveyed seniors, "What is a question, which was easy to answer, that you enjoyed being asked on the first date?"

Here are the TOP 10 answers:

  #1 )  What makes you laugh the most?

  #2 )  What is your biggest passion right now?

  #3 )  Tell me about your family.

  #4 )  Do you have children? Do you have pictures? Tell me about them.

  #5)  What was the most fun job you ever had?

  #6)  Do you have a bucket list? What's on it?

  #7)  Do you have siblings?

  #8)  Do you enjoy cooking?

  #9)  Are you a pet person?

  #10)  Are there any dreams you are currently pursuing?

How to
Finish the First Date Date Well

How to finish the first date well.

OK. The evening, or, afternoon is coming to an end, and so is the date. What do you do to make a good ending to the first date?

If you had a great time, tell your date. It can be something as simple as, “This was fun.”

Then wait to see their response. It’s good to know where the other stands before going forward.

If you get a favorable response, a simple: “Would you like to do something this Saturday?” Is all you’ll need to get that second date going.

If, however, you don’t really want to see them again, you can simply say something like, “It was nice meeting you.” Extend you hand for a hand shake. And say goodnight.

If they ask you right then if you’re going to call or if you want to do something soon, just say, “No, but thank you for asking.” Smile. Be kind always.

Not Every First Date
Going to Be a Connection

It’s very important to remember that not every date is going to be a connection. In fact, most will not. As you probably can remember, this applies to young people as well as seniors. We're all just people. Not everyone is attracted to each other. So, don't be disappointed if the first, first dates, don't work out too well.

You might make some very nice new friends, but, a really good connection is a bit more rare.

If the date doesn’t work out, move on to another.

There may be a lot of “another” before you meet someone you really feel a connection with. It’s worth the wait. And, the effort.

If it takes a while, don’t get discouraged. Don’t get down on yourself and do negative self talk like: “I’m just not that attractive.” or, “No one wants a guy like me.” or, “This is a waste of time. I’m not a kid anymore.” No, No, No, No, No….

You are an Amazing unique individual. And, believe it or not right now, there is some (more than one someone) who would just love to meet and find someone like YOU. So, keep putting yourself out there. Even if it seems hopeless at first.

Also Remember: Not everyone is going to be a match no matter how great you do on the date. You can sometimes be charming, well groomed, wonderful company, humorous, ask all the right questions, be a great listener.… The other person is very nice. BUT, the date is a dud.

Well, that’s just chemistry. Or, rather, lack of chemistry. Just like everywhere else in your life. We like some people a lot. Others we don’t. Just let it go and move forward.

The important thing is to move forward. It’s no big deal. If you keep going, you’ll find some real nice!

How to Tell Someone
You Don’t Want to Go On Another Date

Sometimes after a first date, you just don’t want to see the person again, BUT, they were smitten with you.

Letting someone like this know you are not interested in them is a delicate conversation. Everyone has feelings, and, everyone deserves to be treated kindly. Going on first dates, as seniors, is not easy for anyone.

Whether you let them know right there in person, or, later on a phone call (DO NOT text it), keep your words polite and kind and respectful, but, still be direct. You don't have to reciprocate their feelings to treat them kindly.

You can tell them something simple like: “You seemed like a very nice person, but, I just didn’t feel a chemistry. I don’t want to get together again.”  It can be that simple.

Everyone has feelings, and, everyone deserves to be treated.

Can You Find
A Meaningful Relationship?

Can senior dating lead to a meaningful relationship? YES!

You're never too old to find romance.

"Can seniors still find a new meaningful relationship?

Of course they can. You can too. If you keep trying.

If you don't have a lot of social connections, there are some excellent dating site for seniors. If you don't know where to look, here's a great article specifically about that topic from Forbes Magazine.

You’re a pretty terrific person. Remember that. And, know that there are some pretty terrific people that would love to be with you!

Some seniors will connect on the first date and spend the rest of their lives together. But, that’s rare.

Most seniors (the same as young people) will need to go through a bunch of first dates. And, second and third dates.

Some, will need a lot of first dates.

That’s OK too. All that matters is that you don’t stop looking.

Remember: “There’s a lid for every pot.” That includes YOU!

One More Thing:

Don’t Be Afraid to Ask a Man Out on a Date

Ladies, this is a monumentally important thing for you to know:

Most women don’t realize just how much a man likes being asked out on a date.

It’s true. As men, if we’re 20, 80, or anywhere in between, beings asked out by a lady is so flattering and always makes us feel important and desirable. Whether it’s for the first date, or, any time thereafter. And remember, as seniors, men don't get ask out a lot. If at all. So, each invitation is quite special.

No. You don’t want to ask more than once if he says no. You don’t want to be the one that always has to take the lead either.

But, if you’re getting along and enjoying each others company, once in a while (not all the time), ask the guy if he’d like to go out for dinner. Or, to an art gallery. Or, a poetry reading. Whatever. It doesn’t matter.

A simple casual invitation like: “If you’re not busy on Saturday afternoon, would you like to go to the art show in town together?”

Or: “Would you like to get together for dinner this weekend?” is enough to let the man know you are interested.

As a side note, guys, especially when they haven’t dated for quite some time, can get very shy. Such was the case with my friend Bob who hadn’t dated in 20 years. He said he just didn’t know what to do.

He also said, he didn’t know if the woman he was interested in was even interested in him at all.

And, that is something that happened to a lot of us even way back in high school. Remember the crush you had, that you never mentioned, that never had a chance because you were too afraid to talk to the person? Only to find out years later, that person wanted to go out with you too?

If it’s for a first date, the shy man, might really like you but be very nervous about asking. Don’t you be afraid to ask. It’s OK to do.

The worst that can happen is you misjudged and the guy says “no”.

The earth won’t open up and swallow you. All you friends won’t disown you. You won’t be cast out of society or your home….. And, another wonderful man is just waiting to say, “Yes!”.

The First Date as Seniors


The first date can be more nerve wracking for us seniors than for teenagers.

The thing that really makes for a good first date, according to our surveyed men and women, is good conversation.

Above we gave you lots of good questions to ask to get the ball rolling. We also gave you the questions that will stop almost any first date from being followed by a second one.

Just Remember These Four Things:

   #1)  Be interested in the other person.

   #2)  Be a good listener and really interested in what they have to say.

   #3)  Don’t get too personal. Don’t ask about finances, wellness problems, politics, family problems, sexual history, the exes,…

   #4)  Always be kind and respectful.

If you do that on the first date, you're sure to have a very nice evening or afternoon!

The first date when you're a senior citizen.

Now, Go Have a Great Time! ~ William, Fiona, and Charlotte

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