Dating in the Middle Ages |

I've been holed up with warm soup and painkillers following the extraction of my errant gallbladder, so this week's post is written by my talented and frighteningly experienced sister, Karin. Enjoy. 🙂

No, no, no…not medieval times, apologies for the misleading heading. I'm talking about being middle-aged and stepping out into the world again to date middle-aged women.

I've given up dating for the time being because…well…it's just too hard. There, I've said it. I've done the rounds of dating websites a few times, been on a few dates and decided that the Next Best Thing is just going to have to walk into reception where I work, make eye contact with me and decided that I too am the Next Best Thing.

I thought that those men making the momentous decision to look for a new partner might like to know a few things I've learnt from my little expeditions into the world of singles and so I've made a list. Are you sitting comfortably? Good, then I'll begin…

Firstly, don't mention the ex, except in passing, maybe in connection with any kidlets you've made together. Certainly, refrain from referring to her as That Bitch and please please don't tell me about the whole family law court proceedings you've been through and how she wiped you out. I work in the legal field. I've heard it all. And strangely enough, my sympathy levels drop quite low having listened for an hour to this drivel on an unsuccessful date some time ago. Coupled with the fact that he let a fly sit on his face for minutes at a time just put me right off. Brain into neutral – smile and look polite until time is up. That's all you need to do.

Love hearing about the kids. Tell me all about them. So long as you don't refer to them as ungrateful, little shits, or how That Bitch never lets you see them. I'll show you my photos if you show me yours. Kids are great and I get along with most ages, having two of my own of widely spaced ages. If all goes well, I'll look forward to meeting your kids, seeing how you are with them, how they are with you, and later if all goes well, you will have the pleasure of meeting my two oddball children.

Most women are actually not interested in whether a man has loads of money, work prestige, a fancy car or an extravagant lifestyle. Most single mums are only concerned about whether they have to taxi their own way home, or prevent a potential new man in their life from hitting them up for money. Most of us work full or part-time, juggle a mortgage or rent with paying bills and often without help from the children's father. It is sufficient for most of us that you can pay for a date – and the decent ones amongst the sisterhood will definitely return the favour when they can. And if your car has air con and heating, well, you're onto a winner there.

And speaking of dates, the decent ones amongst us don't need extravagance either, except for special occasions. My dream date always involves food, but not the expensive sort. Chinese takeaway, fish and chips, and a movie to finish off are all magic in my eyes. I don't get out much, certainly not after dark with no car, so little luxuries like this brighten my world. I'm not much of a ‘walk along the beach' kind of girl, but I do love to see the ocean and feel the wind in my hair. Mix it up or down but don't bankrupt yourself.

Set Your Expectations

Have realistic expectations of what you expect in a woman who will date you. Are you a little podgy around the middle, thinning on top, have trouble keeping the buttons closed across your tummy? Then accept that women who may date you will have their own bits and pieces that have gone slightly askew. Most of them will have had kids and will sport the attendant scars and shape-shifting curves. But man oh man…do they know stuff. Any middle aged man who thinks he's going to nail that twenty-something blonde at the bar had better be a rock star or gangster because, well, it might happen, but be realistic. A middle-aged woman is going to be more forgiving in the body department than a youngster will and by all accounts, so should you.

Finally, take care of yourself. And I'm not just talking about wearing clean clothes, keeping your teeth clean and your hair washed, but please do. Take care of your happiness as well. Count your current blessings and let it show on your face. Be glad that you have working limbs and a brain and be grateful for the myriad little joys all around you and filling your life if you take the time and effort to look for them. A happy person attracts a happy person. Share the joy, be kind and thoughtful, share a joke, gain a laugh from a stranger, and be grateful that you are alive to see a sunrise and a sunset.

Then if you've made it this far, you'll probably be in with a shot.

By Karin Lederer


*I've written a book about killing off your debts, called The Debt Cure. In it, I explain exactly how I got myself out of debt and how you can do it, too. Fully illustrated and only 40-pages long, you'll knock it over in less than 45 minutes. Download your copy now.


Other Resources

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Thanks for stopping by and I hope we get to hang out more in the future. And in the meantime, please feel free to share your own experiences. You can email me directly at I respond to all emails. If this was beneficial to you, please consider subscribing and sharing with someone you think would also benefit. 

Disclaimer & Disclosure: I'm not a psychologist, and I'm not a financial advisor's elbow. This material doesn't constitute financial advice but rather a collection of personal opinions, based on my own experiences. Some of the links on my site are affiliate links, which means that if you make a purchase, I will earn a small commission. This commission comes at no additional cost to you. I provide links to services or products I have used and liked or researched and recommend. Please do not spend any money on these products unless you believe they will be beneficial to you

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