Cosmo got lucky when he started dating in later life. We met on the second first date he had. We both knew right away that this was it. He was done with first dates.
I had countless first dates and, like most people, they ranged from good to okay to horrible.
Even though Cosmo didn’t have as many first dates as I did, he understands as well as I do what an impact first dates have on you, and he writes about it often.
Here are 13 articles I’ve written about my first dates, and some lessons learned, so you won’t stumble as much as I did . . . followed by 9 articles about first dates written by Cosmo.
But before you even walk into your first date, work out your dating game plan.
This will help you know which people to rule out and avoid, so you’ll waste less time dating people who are wrong for you.
13 Articles About First Dates Over 60 From a Woman’s Perspective
Unless you’re very lucky, you’re probably going to have a lot of first dates, and many first-and-only dates.
In my experience, most of us need to be willing to devote a fair amount of time to dating.
Successful dating requires preparation and planning. And it requires setting your deal breakers; the things you will and will NOT accept in a partner.
If you don’t know what kind of person you’re looking for, how will you know her/him when you meet them?
In general, it also involves some calculated risk-taking. Meeting people you don’t know and spending probably at least an hour with them is a bit of a risk.
You’re putting yourself out there and need to be somewhat emotionally vulnerable to make an emotional connection with people who are probably strangers to you.
The risks involved with meeting strangers can be minimized by taking basic precautions, as you’ll see in the article.
If online dating feels alien to you or you’re afraid of it, I urge you to reconsider.
Go ahead and network with your friends and family to get dates, but also step into the online dating world.
Unless you have a very robust network of people who may know of people for you to date, online dating will probably provide many more prospects.
A good place to start is eHarmony, our readers’ favorite dating site.
Click on the link above and read my blog post for advice based on my own experiences with online dating.
Not everyone you date will be a good conversationalist, which can lead to awkward first date conversations.
I mean those sometimes agonizing silent pauses when neither of you can think of anything to say.
I never faulted anyone for lacking in this way. After all, first dates can be especially stressful and make even a good communicator falter.
In fact, I usually presumed there may be uncomfortable pauses, and planned ways in advance to smooth them out.
A bit of advice: Make your first dates be coffee dates, or somewhere that doesn’t require you to wait it out until the check comes.
Also, if the conversation is really awkward, you can scoot off to the bathroom to regroup.
I had many first dates in my over 60 dating life.
In my experience, women typically put much more thought into what they wear (on dates or for anything) than men do.
I had several first dates who showed up looking (and smelling) like they’d just finished mowing the lawn, or had done some kind of manual labor minutes beforehand.
And several who paid no attention to how awful their breath was. How hard is it to just pop in a mint before you walk into a date?
Keep this in mind: If he doesn’t care enough to look presentable on a first date, he’s showing you what his normal state is.
Most people understand that you want to make a good first impression on the first date, so you put your best foot forward.
Will Rogers is credited with saying:
“You never get a second chance to make a good first impression.”
If your date shows up looking unkempt and unclean, things are likely to get worse if the relationship progresses.
Going into another first date, your hopes are high, your anticipation palpable. You hope she or he will be the one, so you can get off the dating merry-go-round.
You’ve planned what to wear and, if you’re smart, some things to discuss to break the ice.
But have you thought about what things you SHOULDN’T discuss on this first meeting?
In my 2 years’ dating experience, I was often amazed by what men came out with on our first date.
Read my post for some of the worst offenders I experienced.
Most of what you read about mature dating is negative.
Dating sites warn of all the mistakes people make and all the bad things that can happen.
Cosmo and I are as guilty as anyone. We write a lot about the negative aspects of dating, for both men and women over 60.
Our intentions are good. We’re trying to help others navigate the often rocky road of mature dating, and learn from the many mistakes we made.
But it’s good to look at the lighter side . . . at least once in a while.
So for a change, let’s have a little fun with dating, and keep the mood upbeat, as I tried always to do when I was in dating mode.
I remember well the first few first dates I had, when I started seriously dating.
In my late 50’s, I was looking for a serious long-term relationship
I can still feel how scared I was then.
My head was filled with crazy notions about the men I might be dating. I assumed that the vast majority of the men on dating sites were losers of some kind . . . scammers, ghosters, fleecers and otherwise nefarious and dangerous people.
I couldn’t have been more wrong, but I didn’t learn that for several months.
In the beginning, first dates were agony.
My expectations were high and unrealistic. The pressure was pretty intense.
Over time, my thinking leveled out, and I came to almost enjoy all those first dates . . . and, believe me, there were plenty of them.
In the article, you’ll find some of the things I learned that can help you diminish the negativity.
First dates can be stressful. It’s easy to be nervous and do dumb things. If there were enough good things going on during the date, I didn’t sweat the nagging little things.
But then there were the men who were just plain insensitive.
What really got to me was when they were so impulse-driven – or just ignorant – that they did what felt good to them . . . without caring if they overstepped and made me uncomfortable or creeped me out.
Here are 3 of the 5 dumb things some men do on first dates:
- Pressing the woman hard to go to dinner, when she suggests just going for coffee.
- Lashing into their ex at length.
- Taking out a list of questions and running down each one (I swear, this happened to me).
Read my post above for the other 2 things, and this post for more of the same, 3 Dumb Things Men Do On First Dates That Can Ruin Everything
Unless you’re very, very lucky and meet “the one” quickly, you’ll be doing a lot of dating.
And that’s okay. It’s good practice to go on lots of dates. It helps you get better at reading people and knowing who will or won’t be good for you.
Try not to set your hopes too high with each new date. Just think of it as getting to know another human being a little bit.
In my post, I offer a few things to plan for and think about, as you go on first dates, second dates and beyond.
You need to be mindful of various things to make your first dates more enjoyable, safe and successful.
Two smart first date tips include:
- Don’t rule someone out based on frivolous things but, at the same time, pay attention to your first impression of them.
- Drink very little alcohol, if any, on a first date.
Read my post for the other three.
Do you think the secret weapons have to do with something like dressing to kill? Or smelling good? Or meeting at the perfect location?
No. It’s much simpler than that.
Read my post to find out.
Early in my second dating go-round, I had a doomed, painful first-and-only date with a man I met on a dating site.
I’m not likely to ever forget it, because no other date made me feel so small.
I neglected to do something I now advise all people dating should do: Always trust your gut instinct about someone you’re dating.
In hindsight, I probably saw the signs that he wasn’t for me in the few emails and phone calls we exchanged before meeting. But I think I was still getting my dating sea legs. I too easily gave people the benefit of the doubt, even when I shouldn’t.
Read my post for all the gory details.
9 Articles About First Dates Over 60 From a Man’s Perspective
We’re firm believers in using a little introspection to improve your dating life. Yet not everyone is so inclined.
So for you guys that just want to get out there and date without too much thought, here are some old sayings that will probably keep you out of trouble. There’s usually a grain of truth to most clichés.
“You never get a second chance to make a first impression.”
“We marry our parents.”
Read the post for more sayings that ring true.
Some of these first date conversation killers were said to Daisy or me on our first dates. Others we heard second hand. And others were compiled from articles about the thoughtless things people have said or heard on first dates around the world.
Yes, there really are this many things that shouldn’t be said on a first date.
But don’t worry. It’s not like you have to memorize a list of a thousand things to not say. At the end of the article are simple tips to avoid putting your foot in your mouth. That way you can relax, have fun, and have a great conversation as you get to know your dating partner.
Remember, the first date is where each partner is simply trying to find out if they enjoy the other’s company. It’s not about finding out every last detail of their lives. Those things will come out in later conversations.
It’s natural to want to learn about the person you’re planning to meet for that first date. Perhaps the first thing on your mind is a prudent concern for security, whether you’re a man or a woman.
Yet there are other reasons you may want to do a Google search of your potential ideal partner before heading out on that first date, like:
- For things to talk about on the date
- To see if they’re honest on their dating profile
- To find out if they’re married
- To eliminate major red flags
There are also some pitfalls, like:
- Obsessing too much about potential dates
- The possibility that you’ll reject good candidates
- Making assumptions based on incomplete information
- Not using the information you find sensibly
Sometimes a little laughter will lighten your load when you’re dating. A good laugh is restorative.
If you don’t believe me, take a few minutes to check out these funny worst date stories from some of our favorite TV sitcom characters of the 70’s, 80’s and 90’s.
Go to the post to see hilarious clips from shows like Everybody Loves Raymond, Frasier and The Golden Girls.
One of many good reasons to date mature women — they lie less frequently than women younger than 45. Men also lie less as they age. Perhaps that’s because as we mature, we generally accept who we are and we’re looking for people who will take us as we are. There just isn’t time for games and deception.
Nevertheless, lying in online dating profiles and on the first date or two is pervasive enough that we should remain mindful.
You may be surprised by the things women lie about. Check out the post for the details.
If you’re a man over 60, it’s quite possible you’re re-entering the dating scene after a death or divorce.
Perhaps it’s been many decades since you’ve been on a date.
Technology has evolved at warp speed. Online dating might feel like an impenetrable, puzzling world better left for millennials.
And where do you start these days with offline dating?
Read the post for plenty of sound advice about how to find and connect with the mature woman who could be your true love.
There are a number of simple, maybe obvious, things everyone should be mindful of, if they hope to turn first dates into second, third and fourth ones . . . and beyond.
Two of the simple tips Cosmo points out in this post are:
- The Importance of Self-Care
- Be Aware of Your Body Language
Read his post for 2 more.
Cosmo suggests in this article, and I agree, that it’s better not to drink at all on first dates.
He describes a first date of his that went wrong fast, because he didn’t trust his gut and say “no” to this date.
Read the post to learn what he learned from his poor dating decision-making.
How do first dates make you feel? Nervous and anxious or eager and excited.
Or is it a heady mix of many emotions? If you’re an introvert, like both Cosmo and me, you’ll tend to a little anxiety and nervousness. Meanwhile, extroverts relish the thought of a new first date.
Whatever your personality type, be aware of how it might change your dating behavior. For instance, an introvert might be even more reserved than normal when meeting someone new. An extrovert might be so driven by an adrenaline high that they overwhelm their date with non-stop story-telling.
In his post, Cosmo describes five easy ways you can improve your dating skills and make that first meeting a great one.