Five things I’ve learnt about dating in your 50s, by a man newly single after 28 years of marriage

When our guest writer, now in his 50s, became a widower, he wasn’t sure how to date again. He has some great advice – from personal experience! – for 50-something men going on dates

After 28 years of marriage, I found myself exactly where I didn’t think I would be: alone. My wife and I met in our early 20s, married a few years later and built our lives together.

But now, in my 50s, I’m alone. My wife fought a two-and-a-half year war against cancer, but in the end it overwhelmed her. As a family, we were devastated.

My choices were simple: sink into a deep, lengthy depression or start living again. I decided on the latter and that meant, at least in part, meeting women. Not just for friendship, but to develop a relationship, sexually and emotionally. But to get there and do that meant dating. Yes, gulp, dating.

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Women in all likelihood have put up with someone like you – and are not likely to do it again

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In our 50s we carry a lot more baggage, or luggage, or life experience. It all amounts to the same thing, and it’s how you deal with it that’s important.

If you’re going to start dating in what some call life’s ‘third quarter’ here are a few basic tips to help. I should say upfront that I feel as good in my 50s as I did in my 30s. I still have a ton of energy, I’m excited about life and I think it’s fun to meet new people. Anyway, here’s what I found useful on my quest.

1. Be honest

If you tend to exaggerate your worth in the world, embellish, tell tall tales or generally string a line of BS, women will see right through you. Women are incredibly intuitive and in all likelihood have put up with someone like you – and are not likely to do it again.

Here’s a failsafe solution: just be honest. It works every time. Tell her your interests, what your children are like, your career highlights and lowlights. Be ready to come clean, because she will know immediately if you’re not who you say you are.

2. Get your body in shape

In our 50s, our metabolism slows down and our ability to gain weight increases. I have always been a runner, hitting the streets three to five times a week, accomplishing five to eight kilometres at a stretch.

I made a renewed commitment to running, watched what I ate and cut down on my alcohol consumption. It won’t take long for you to notice some results, but you’re going to have to stick with it.

Remember, you want to present yourself as in shape and active. Everyone has a few pounds to lose, and that’s entirely understandable, but you’re going to have to make an effort.

3. Pay attention and be a gentleman

Listen to what she has to tell you. Get to know her and find out her story, where she comes from, what she does for a living, her likes and dislikes.

Especially listen to what she says about her family. I’m looking for a woman has a great relationship with her children and her parents, so I want to know about her family trips, traditions and their love for one another.

To me, any sign of a dysfunctional family could be a red flag, so I pay attention to that. Also listen for conversation about her ex-husband/boyfriend. You’re trying to get to know one another, not each other’s ex.

And remember your manners. I think you should always pay for dinner, with no expectations. It’s the gentlemanly thing to do.

4. Learn to cook

As your relationship progresses you’ll want to start spending more time at each other’s place. She may cook for you and vice versa, so find out some of her favourite dishes. Don’t try to reinvent the wheel: follow the recipe and leave yourself good time to prepare prior to her arrival.

She will love the fact that you went out of your way to cook, regardless of how well the meal turned out. The point is that you made the effort.

5. Up your personal game

Clean up, get a shave and a haircut. Buy some new clothes. Develop a fashion sense.

Cut down on the alcohol, learn something about wine and enjoy it.

Try something new. It’ll help you meet new people as well as have something interesting to talk about. I took up downhill skiing, which scared me to death, but I did it and it’s kind of fun now.

Buy a new aftershave: smell good and look good.

Above all else, make sure you have fun.


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