Top tips for dating in your 40s

Have you recently come out of a long term relationship? If you are over forty then you might be nervous and apprehensive about returning to the dating world. Here are some tips that can make things far easier for you while you’re dating in your 40s.

To Filter Or Not To Filter

dating in your 40s

The most common way to date these days is through dating apps. This idea brings an important question. What type of photos should you add to your profile? Some people swear by filters and touch ups while others see them as dishonest. Well, this is always going to be a personal preference. The truth is there’s nothing wrong with filters as long as they don’t completely alter the way you look. If you do this then you might get the first date but there may not be a second. It’s better to be honest about who you are. This is important when listing your age too. Tempting though it may be, you shouldn’t list a younger age. Don’t worry, there’s plenty of people out there looking for older men or women. 

Find The Right App 

Next, you should make sure that you are finding the right app that is going to provide the best benefits that you need. You might think that there are only a couple of apps, but this isn’t true. There are various apps worth exploring and even more websites. If you want to ensure that you get the best experience it’s great to explore as many as possible. Apps that you should stay away from are ones where you need to pay per message. These will almost always be a scam. Make sure that you check reviews for any site or app that you are thinking about exploring. 

Be Smart

dating in your 40s

You do need to be smart when you are planning your dates. For instance, you should make sure that you are meeting people in a place that you know and feel comfortable. It’s also advised that you do ensure that you video call first. That way you can guarantee that you do know who you are meeting and avoid the catfish. 

Remember, there’s no harm in going on as many dates as you like to find the right match. But you should get tested using a professional medical centre every time you  have a new partner. 

Don’t Fear Rejection

Finally, it’s important to understand that you will experience rejection in the new world of dating in your 40s. It’s a given and if you are a woman that’s because men swipe right 80% of the time. However, this doesn’t mean that they will always be interested in having a conversation or moving towards a date. Don’t be disheartened, move on to the next match. It’s always going to be their loss, not yours. 

We hope this helps you understand some of the key steps that you should take if you are returning to the dating world at 40. The good news is that there’s plenty of people doing this these days that are back on the playing field at a later stage in life.

Are you dating in your 40s at the moment? How’s it going? Comment below, we’d love to hear from you.

Spinster Chronicles: The one with the breakup text

Are you dating in your 40s? Have there been any unexpected challenges? Technology has advanced so much since our 20s that it’s not uncommon to have a text message relationship before even meeting each other. Well, imagine being sent a breakup text before you’ve even had your first date….Meet our favourite spinster, Jennifer Walters.

10th June 2021

Have you ever gotten a breakup text from someone you didn’t know you were dating, someone you’ve never even actually met in person?

Well, neither had I, until last week.

CfromTinder texted me to let me know he’s had enough of me not putting forth the proper investment into our budding relationship and he’s not interested in a woman who won’t make him a priority.

I told CfromTinder that I have two kids, two dogs, a job, and as of late I spend a ridiculous amount of time watching videos on the internet about fixing broken toilets because for the past several weeks, at least one of them in my house is out of order at all times.

I also told CfromTinder that he is right. It’s highly unlikely I would make him a priority because I’m not really interested in knowing someone that is hard work to know before I even actually know them, because I’ve never met them, in real life.

Two days later CfromTinder texted me to say that he thinks he jumped the gun and wants to give it another try. I told him we probably wouldn’t be a good match, but his persistence, combined with my sister’s insistence that his pics were really cute, and my having nothing to do that Thursday night, led me to agree to meet him for a glass of wine.

We met, at the wine bar down the street, where they always see me with a different dude. I have a feeling they may be starting to wonder if I’m some sort of lady of the night.

CfromTinder showed up in purse pants and spent maybe fifteen collective minutes, out of the hour and a half we were there, actually sitting down at the table. The rest of the time he was in the bathroom, at the bar, running to his car for something, or taking a call outside. I’m pretty sure that in truth he was either preoccupied with tending to what I suspect might be a nagging cocaine habit, or suffering from a severe case of untreated ADHD. Either way, my notion that we weren’t a good match was confirmed. 

Back to the swiping board. And no, CfromTinder, I’m not going to meet up with you to explain why I don’t want to see you again.

9th July 2021

I met B online. B is a Marine, but the true display of his bravery came when he agreed to meet me for the first time while I was out on a girls night. He survived the shenanigans and interrogations from my besties, so when he invited me out on a real date I accepted.

We went to my local wine bar (yes, that same one I go to on all my dates) and had a nice time. During our evening, we realized this was not the first time we’d met. Not only was it not the first time we’d met, he had been to my house before, been swimming in my pool, sampled my world famous guacamole, and maybe even pooped in my toilet. I don’t know if he actually pooped in my toilet, but I assume since he was there for several hours eating snacks, it’s very possible.

We also discovered we have a mutual nemesis. The same evil twat that wreaked havoc in my life wreaked havoc in his, during the same time period. Apparently she was so masterful at being an evil twat the it was no problem for her to fill this role for multiple people in parallel. We bonded over this hatred for TwatyMcHoebag and decided to go on another date.

As the week progressed, we discussed possible next date activities. I suggested maybe bowling, axe throwing, or painting. He said he didn’t want to do those things. I said, “okay,” because I’m a reasonable human being who doesn’t try to convince people they like to do things they don’t like to do. He suggested we go shoot guns. I told him I don’t like shooting guns, and rather than him simply saying, “okay,” B, who shall henceforth be referred to as Pushy McPusherton, spent several minutes too long explaining to me how he could change my mind about shooting guns, and that I should ignore the likelihood that I would have a trauma induced emotional breakdown if we shot guns on our second date.

I told him I’d think of some other ideas and call him back. I did not think of any other ideas, nor did I call him back.

Jennifer’s Top Tips for avoiding text messages

For those of you who love to complain that you get too many text messages that you’re too busy and too important to be bothered with, but can’t seem to figure out what to do about it:

1. Turn your alert off. You may not know, but you can turn both your audible and vibration alert off, unless you have a phone from 1994.
2. Turn your phone off. Although this may interfere with your ability to interact with others, you’re clearly in pursuit of less interaction, so, win!
3. Get a bag phone. They can’t receive text messages.
4. Give your phone to a toddler. Let them answer your texts. If you don’t have access to a toddler, give your phone to a dog. If neither of these options are at your fingertips, put it in the toilet.
5. Stop giving people your phone number.
6. Get a pager.
7. Activate the Do Not Disturb feature on your phone. You likely have this feature on your device, unless you have a bag phone, in which case, problem solved.
8. Build really thick walls in your house so the signal can’t get to your phone when you’re inside.
9. Fashion yourself track suit with signal blocking technology that you can wear around town. It is critical that your suit has a pocket to securely transport your device. I suggest a zipper closure as Velcro often losses it’s locking power with wear and tear.
10. Remove the battery.
11. Never, ever charge your battery.
12. Switch to walkie talkie technology.
13. Every time someone texts you, text them back a picture of you making a mean face.

You can catch up on Jennifer’s debacles here. Do you find dating in your 40s challenging? What are the most random messages you’ve been sent?

Leave a comment below and follow us on Instagram here where we’ll be keeping the conversation going.

The Spinster Chronicles: When first dates feel like job interviews

Are you Bumbling your way through apps and online dating? Do first dates feel just like job interviews? Our favourite spinster Jennifer Walters is back, candidly sharing her dating debacles with us.

First Dates: The Interview Process

‘I don’t like to talk to people on the phone. I barely like to talk to most people in person, but voice to voice with someone who I’ve only known as still images of him and his dog or posed candids of him scaling Mount Everest is extremely painful and accelerates my normal awkwardness toward a full blown display of embarrassment during which I forget simple English and fun facts such as how old I am.

In-person there would be, at least, wine and fake smiles to fill the inevitable conversation lulls. During a recent interview, I mean phone call, I found out that Dude is very enthusiastic about their career but also super excited about his new adventures in snow sports. He told me how much he works out and how he enjoys wine but only sociably because he doesn’t like to “overdo it or anything.” He ended the conversation abruptly because he got a call from his sister in the midst of me sharing with him how often I DON’T work out, how often I DO drink wine with ZERO dependency on whether or not I am in a social setting, and my complete lack of desire to ever do anything that involves snow.


He did not call me back. He did, however, send me a message on the dating app informing me our conversation was “dry” and we probably shouldn’t bother talking again. I can’t say I disagree but for some reason his acknowledgment of the obvious was quite the blow to what’s left of my already defeated ego. A mutual ghosting would have been much more polite. All part of the first dates interview process I guess.

11th February 2021

I was supposed to go on a date last night. He cancelled on me because something came up with his son, he had an appointment to show a house he forgot about, and he couldn’t figure out his password for the Higamahoo website, but hoped I’d give him another chance on another day.

I told him I understood things with kids, empathized with his inability to logon to and yes, I’d give him another chance, although he clearly might have time management issues if he booked a showing and date with me for the same time, same day.

I then realised I didn’t know his last name and should probably figure that out so I can search for a criminal record before we make plans again. I googled his phone number and found a last name that looked familiar, familiar as in New Guy has the same last name as Poop Doctor. (See previous Spinster Chronicles article)

I then googled New Guy and Poop Doctor together and found an old blog post from Poop Doctor talking about his life (which he thinks is amazing, if you don’t recall from when I told you about my date with Poop Doctor a few weeks ago), including how excited he was when his baby brother New Guy was born. I texted New Guy and asked if he had a brother that is a poop doctor. He does. I mean, come on, what are the chances?

13th April 2021

It was seven o’clock, on the dot, in my drop top – kidding – I just have that song stuck in my head, which is odd because I usually only get that song stuck in my head around midnight when I can’t sleep and should be counting sheep. Instead, I am fantasizing about meeting Usher in the Harris Teeter parking lot after hitting his expensive car with a shopping cart, our subsequent falling in love, being endlessly harassed by the paparazzi, and me eventually breaking his heart because I’m not cut out for a superstar lifestyle.

It was actually seven forty-five-ish and I was in the midsized SUV that I purchased after years and years of shaming from my sister-in-law for driving a “mum van”. I pulled up a bit nervous because MfromTinder had some questionable fashion choices in some of his profile pics. But as my friend and confidant Stacey says, “it’s a lot easier to get a man to give up a bad chef pants habit than a bad cocaine habit,” something with which we both, unfortunately, have way too much experience. So I proceeded with cautious confidence that he wouldn’t be dressed like a Culinary Arts student from my mid-1990s high school vocational training program.

MfromTinder texted me to let me know he was running late because he went to the wrong restaurant. Midway through my glass of wine, I decided I’d prefer if he didn’t show up at all because I was really enjoying my book, but alas, he arrived. It was okay, and when I say okay, I really mean it was meh.

The few funny moments were completely cancelled out by the inappropriate questions that proved he was probably too much of a jackass for my liking. He was also shorter than he said on his profile, so, yeah, ugh. When he walked me to the car he went in for a kiss. I dodged it masterfully and instead delivered the most majestic high five of my life. The crowd cheered at my agile and victorious performance. I had another date the following night, which was another first dates disappointment. I did, however, confirm that if the dude is wearing sunglasses in all his pictures, there’s a chance he is a pirate.

For the love of Tinder

I have made some new and special friends during the first dates interview process:

1. Aquaman with the dad bod, who promises he will end my streak of no second date by taking me to dinner AND drinks, in the SAME night, before he ghosts me.

2. Captain Sadness, who can’t stop telling me about how much he misses being married and can’t wait to have a new mum for his kids.

3. Mr. Toughguy, who says, “if you’re a feminist, you’re paying the check and I’m getting two appetizers.”

4. Chief Bot, who obviously is a robot using some extremely attractive man’s stolen internet headshots.

5. The Counsellor, who wants to talk way too much about my dead husband. And, of course,

6. The guy who asks if I can come over, right now, at 2am.


Are you dating in your 40s at the moment? How are you finding the first dates? Leave a comment below and follow us on Instagram here where we’ll be keeping the conversation going.

Dating over 40: The Spinster Chronicles

Wondering what the truth is about dating over 40? Maybe you are in the throws of Bumbling or have your own fair share of Tinder disasters to share? We just know you’re going to relate to our new column: The Spinster Chronicles! Headed up by Jennifer Walters – a confident and gorgeous 40-something woman from North Carolina. Sadly widowed far too young, she continues to work through her grief and ‘is figuring out how to make the most of life.’ While doing this, she has diarised her hilarious dating over 40 disasters on social media, and now we are bringing them to you at 40 Now What!

The truth about dating over 40

My real first date was with a guy I met on an online matching website. 

His profile said he was a six foot two redhead who was fond of the local wine bar that I often frequent. We decided to meet there for a glass of wine.

I arrived early, so I could pick a good table and have a few sips to calm my ‘haven’t been on a date in a long ass time’ nerves. 

Thirty minutes and a glass later, I got a text from Redhead saying he was outside, but not sure if he should come in. I told him that he should. He asked if I was sure. I said yes while wondering if he was hesitant because he had phoned a friend that was acting as his informant on the inside, who told him I looked like a troll.

I finally convinced him to come in, but I didn’t see him. Instead, a five foot two man in a shirt two sizes too big sat at my table. I thought it an odd coincidence because he too had red hair. To my dismay, this little man introduced himself as Redhead as he sat down.

Redhead ordered himself some wine. As we chatted I learned he didn’t seem to have a job that was real, a kid he didn’t see very often, and a dog he really thought was the cat’s pajamas.

We wrapped up the night with him giving me a pat on the back and the words ‘let’s just use this as your first practice date.’ He then left me with the bill, a tremendous sense of bewilderment, and a promise to myself that if a leprechaun ever showed up to meet me for a date again, I’d pretend I didn’t see him or his lucky charms.

16th January 2021

I went on a date earlier this week. It was with a poop doctor I met online. And although I would never admit to online dating years ago before I was married, apparently that is what people do now, because for some reason men no longer believe in actually talking to a real life woman face-to-face without first spending weeks on meaningless chit-chat hidden behind an online profile picture. 

He spent the entire night talking about his job and using words that you wouldn’t understand unless you too were a poop doctor, interrupting my responses whenever he shocked me with a question with questionable interest in anything about my life. Then he told me of his incompetent assistant, who was obviously hired because she’s so pretty, which he stated I can probably relate to because my looks have surely helped my career too. He wore pants with a subtle checkered pattern which I chose to accept as acceptable, because the print was subdued and his, well, his biceps. I spent most of the night trying to figure out if he was a douche, nervous, needed a recommendation for a good therapist, or maybe worth a second date because he was kinda funny. 

The next evening I sent him what I thought was a very thoughtful text, full of recommendations of things to do in a city he would soon visit. He responded the following evening, with a meme. WITH A MEME. I’ve not heard a peep since, which is completely on trend when my dating life for the past two years. 

Between the men who don’t actually ask me out after endless flirting and these weirdos that I never hear from after a first date, it’s a good thing I have my amazing imaginary knitting circle friends and invisible hairless cats. I think I will stick to evenings alone with my television programs and start looking into joining a bridge club. 

Who can teach me how to play dating over 40?

‘I have such a magnetic draw for oddballs.’

22nd January 2021

I went for a bike ride today. That’s a lie. I don’t ride bikes. I was really just walking my dog.

During my casual stroll, as per usual, I was reading my book du jour on my phone when a young man who looked like a cross between Jack Black and Napoleon Dynamite rode up beside me on his ten speed.

He stopped next to me and proclaimed, loudly and enthusiastically, ‘I love older women!’

I asked him how he knew I was older than him and he told me it was obvious and he’d love to take me to dinner.

I told him I don’t go to dinner with younger men who I meet on ten speeds while walking my dog.

He said please. I said no thank you.

Jack Black and Napoleon Dynamite then pedals off, leaving me feeling slightly flattered, slightly insulted, and wondering if I should finally learn how to ride a bike, and why I have such a magnetic draw for oddballs.

You can follow Jennifer and her dating over 40 mishaps on instagram @spinster.chronicles and follow us on instagram @40nowwhatmag.

Have you had any dating disasters in your 40s? Comment below.