The Perks of Dating (And Flirting) At Forty

By Guest Blogger Amy Larson

It feels like just yesterday I was wearing big hair, jelly shoes and bracelets, rolled sleeves on my jacket, and running around with boys that turned up their collars and wore football jerseys in town on the weekends. How did I wind up sitting at a Mexican restaurant next to a mature gentleman with touches of silver around his temples, on my first date in NINETEEN years? It was beyond bizarre.

No dreaming of a white dress and a huge wedding; I’ve already done that and so has he. Neither are wondering what a child would look like if we had one together; our child-bearing eras are over. He’s not sweaty and nervous when he kisses me or asks me on a date; anyone single and older than forty generally knows what they’re doing. Not only has he asked hundreds of women out in his lifetime, he’s also popped the question a time or two. While I had once dated boys, dating an actual ‘older’ man, one with a deep voice and the ability to grow a full beard is both thrilling and strange. This guy has a job, a mortgage, ex-wives, grown children and even a grandchild. What am I doing?

The Perks of Dating (And Flirting) At Forty

As a dating-happy teen, I could just grab my (Guess) bag and run out the door. At age forty and divorced, it’s getting home from work exhausted and bewildered at the mess early-morning dashers left behind, then rides to sports practices and slapping dinner on the table before I can even think about that night’s wardrobe or what I’m going to do with my hair.

It’s trading PMS for peri-menopause, and sun-kissed highlights for whatever will cover the gray that the last romantic go-round gave me. Not the condition I had ever consciously meant to greet the dating world in; but a sudden divorce meant little to no prep time. Why did I date again so soon after marriage? Those who’ve divorced can attest; it’s lonely within the relationship years before those final papers are signed. I desired some company and a much-needed ego boost.

Admittedly, I was ill-prepared. The standard dating advice is to be genuine, be at your ease, and be paying close attention to potential red flags. Now just where and when would I have honed those skills? The furthest my ability went to read people was to know when someone was teething, had to go to the bathroom, or needed a nap.

The Perks of Dating (And Flirting) At Forty

Many of my married friends were visibly uncomfortable with the fact that I was single again. They scrambled mightily to get me un-singled, ASAP. After all, no one likes to see a bench warmer. I knew what was up; they wanted their friend to get back out there and get the crap beaten out of her, just like the rest of the team. Old ladies said: “When I met my husband, he just snatched me right up. He didn’t wait around like you people do nowadays.” Clergy said: “Anyone that knows how to play the game doesn’t last out in the dating world long!” (Thanks pal. No pressure.) Friends and family said: “You’re too good to be single.” (Really, does that mean I did something ‘bad’ to get to this point? Nice.)

Being forty still doesn’t lessen the nervousness factor. If anything, the first time I dated anyone after my divorce, I was more petrified than I ever remembered being as a teen. After my first date, I broke out in hives. Big ones.

Dating at middle age is definitely not for the faint of heart, but there is some good news:

The Perks of Dating (And Flirting) At Forty

If he didn’t like me, it wasn’t going to be the end of my world. I would cry a little but I sure wouldn’t cry all night like I did when I was a girl. I could get by just fine without a man in my life and, amazingly enough, still feel like a worthwhile individual. I didn’t need a boyfriend to validate my existence, nor to complete me. They were nice to have around, and if one of the relationships wanted to ride out the wave, cool. If not, I had plenty of other things to do and an already-full life to lead. Instead of being a pined-for necessity, these grown-up men became invited guests to a party that had already been going strong for a few years.

So if you’re on the fence about dating after 40, or after a divorce, go ahead and give it a whirl. You might just enjoy yourself.

As my heroine from ‘Fried Green Tomatoes’ puts it, “I’m older, I’m smarter, and I have more insurance.”


Tell us, how did you get back in the dating game after divorce or a broken relationship? Was it difficult? What’s it like dating at 40 or still being single at any age, when many of your friends are married with kids? We’d love to know! Share any dating tips or stories you might have.



The Perks of Dating (And Flirting) At Forty

Amy Larson is a non-recovering chocoholic, middle child, and champion truth seeker. If there is any irony, humor, or the absurd to be found, she’ll find it.

Married for nearly twenty years, then divorced, she moved as a heartbroken single mother of three into a new neighborhood and wound up marrying the neighbor down the street. The new husband brought with him his ferret, two grown children, two grandchildren, and a family where parents and four out of five nearby siblings all lived in that same neighborhood. Can we say, “Everybody Loves Raymond: Extreme Edition”?

During her single mom years, Amy, once used to financial security and a somewhat comfortable life, reluctantly found work as a housecleaner. Often while scrubbing and listening to NPR, she thought, “I could do that. I could write like that.” Little by little, she began submitting work to local newspapers, which led to a gig reporting for one of the nation’s top rodeos.  After that, her writing career got busier, and a grateful Amy Larson now writes content for local and state magazines, newspapers, is a weekly contributor to several blogsites, and concocts advertising articles for a daily deals corporation. Her dream job is to be a food and travel writer, because she’d dearly like to have an excuse to both eat and globe-trot for a living. She likes food of all kinds, (especially if there’s a heat factor), and will eat almost anything within reason, as long as it’s covered in chocolate.

  1. Well I am happily married with kids but I still enjoyed this blog post. No dating after 40 tips sorry! I loved your bio.

    1. Shannon: Thanks and so great to hear that you’re happily married. Getting divorced didn’t sway me from the belief that happy marriages are possible. Realize that for those that are not in a good relationship, you’re giving hope. Bravo to that.

  2. I am divorced for 3 years (I’m 43) and the beginning of dating is exciting and new. Then after the pool of men gets smaller and you go on some pretty scary dates it gets a little depressing. Being alone isn’t much fun I have discovered. I’m happy you found love again. Good for you.

    1. Paula: Totally agree with you that the pickin’s are slim. Would be an interesting blog post to explore who’s out there lately…I recall a guy I met at a single’s dance that I swear to you was shaped exactly like a praying mantis (think bent wrists, even!). Big turn-off. Another guy globbed on at church and made it tough to worship there. When I tried to tell him there was nothing between us (nor would there ever be), he harassed me with text messages, continually asking what he did wrong. Wow.

      To clarify, yes I remarried and that’s a happy thing but not without its challenges (you probably saw the bio). Very different from the first time around; it’s another game completely.

  3. i never trusted men. however got married after 30 and divorced after 5 years. he was… well – not to blame. i was alone for several years after realizing that i was totally right about not trusting them. and then i met that guy one day. we started to see each other occasionally – no one could call it ‘dating’ but it was pretty comfortable. in a course of time we’ve got to a point where relationships should turn into next level or to break up. we had a dinner together and i told him that i can’t trust any men including him and that’s something stronger than me. i am very grateful for the words he told that night – it completely changed my life and attitude. and that was simple like that: what is good for you in not trusting men? you never be close to anybody – you’re locked inside. trusting is better cause gives you many chances to live at full. no matter you’ll be betrayed or left alone again – it’s only your attitude and you may change it by yourself. somebody hurts you – forget him. start all over again and never be tired to do so. i trusted that night. i am 55 now and happy.. with him.

    1. Your significant other’s words are oh-so-healing! Essentially ‘what good is this doing for you, and what’ve you got to lose?’ That sort of wisdom– especially when coming from a male–makes perfect sense. If we’re making ourselves miserable not trusting men, then maybe just maybe trusting a man might be the answer. If you find one you decide you can’t trust, toss him and be open to finding one that you can. No wonder you’re 55 and happy; you had the depth to take his advice in and use it for the greater good…for both of you. Loved your comment.

  4. I could imagine how different dating after 40 would be as it is a completely different ball game then dating in your early twenties (before marriage). As a married woman to my childhood sweetheart, I would probably not even know how to date anymore 🙂
    I enjoyed reading this post, Its great you have found love (even with its new challenges).By the way; I am a Chocoholic as well-with a capital C!! Simply could not live without it:-D

    1. I don’t know what it would be like to marry someone I’ve known for so long. Coming off of a long first marriage, I’m guessing very sweet. You’ve essentially grown up together. I’m glad that you don’t know how to date anymore, but I’m sure you still know how to flirt with the man you’ve married. Congratulations on your long-lived relationship; it’s what I like to hear.

  5. Amy, what do you think about flirting and possibly dating even after you’re married? I’ve been reading about the “hotwife” phenomena, which are women who have relationships (usually casual sexual ones) with men other than their husband, with his permission. Other than morally, would you ever recommend something like this? As an example, here’s a blog from a “hotwife”: (careful, though, it’s explicit)

    1. Really want to know my opinion?

      The general idea of marriage is ‘I choose you over all others’. To have and to hold, love and to cherish, that sort of thing.

      You can practice your hotness on the one you said you’ve chosen. If he’s not interested anymore nor does it look like he ever will be again, it’s best to dissolve the relationship rather than going back on your word. That’s more about personal integrity than about him.

      With the ‘hotwife’ phenomena, it’s far more sexy to know that while everyone else might be checking you out, you’re only going to take it home to one guy, who (if he’s smart) knows he’s lucky. The rest can dream about you at best; too bad for them.

      Men are territorial. I don’t care what they might tell their wives in a moment of boredom, wanting an open marriage, etc, once someone else has marked their territory (the ‘hotwife’), he won’t be interested in keeping up appearances for long. Trust me, it’ll only be a matter of time. A woman is better off saving some steps and just getting a divorce if she wants to flirt around; the end result will be exactly the same.

  6. Parted company with my high school guy after 22 great years of marriage. I was 42. Dabbling in online, fix-ups and speed dating was good practice for me. I found the ‘type’ I thought I was attracted to had changed dramatically. I solidified family and friend relationships that had lapsed. Dating was nerve wracking, but got easier with time. After several dates with the same guy in Years 2, 4 & 5 of being single, I suddenly went from nonplussed to ready to recommit. We moved in together with 3 teens and 3 dogs. Now into our 5th year, I am 51 and happy. Happy that he was patient and that I didn’t rush into it.

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  9. Amy made an interesting point. She was lonely within the marriage for years before the divorce, and so quickly jumped into dating again in her desire for companionship.

    She said she was petrified, but she must have possessed the self belief and confidence to get out there dating again after so many years.


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