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Top 5 Worst Dating Mistakes You Can Make in Retirement

On this episode of DETANGLED


Let’s talk about dating, because it seems that many people don’t know how to have fun with it. But here’s the thing: mistakes are normal, and they make you human. They’ll only make your next experiences a lot more enjoyable and exciting. If you want to have a successful date, I have some tips for you.

What are the worst dating mistakes in your opinion?

My best friend is a divorcee, and let me tell you that she’s been on many, many dates since she filed those papers. But let’s start from the beginning: she’s 58 years old, works as a librarian, and was married for 30 years when she and her partner decided that things were no longer good between them. They tried to make things work and become closer again, but that simply didn’t happen.

When she finally accepted that she couldn’t get back together with the man she had been married to for such a long time, she immediately jumped on the dating wagon. But as much as she tried to seem like a great catch, she made a few mistakes that she immediately regretted.

You might think that I’m not the most supportive friend now that I’m exposing all her wrongs, but she’s actually the one who gave me the idea for this article, so if you want to learn about all the dating mistakes seniors typically make, you’ll have to read along with me until the end of this story.

Without further ado, here are the worst dating mistakes you can make in retirement! Let’s begin!

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6. Using old photos

Here’s the 1st dating mistake: when my dear friend felt ready to be on the market again, the first thing she did was to create a profile on different dating apps. She put her age, occupation, height, and interests there, hoping that she would find the perfect match, but one thing that she had some issues with was the fact that she had to put a picture there.

And believe me when I tell you that it took her more than an hour to choose the ideal photo. She hated every single picture that she’d taken 1-2 months before the whole thing, so she used 2-3 photos that were taken 5 years ago.

She was just as lovely, but her hair color was different, her makeup was different, and when she went on her 1st date, the person she went out with commented that she didn’t look quite the same. So, as you can imagine, she decided to delete those photos and be honest with herself and other people, and only add recent pictures.

5. Saying yes too much

I think that this is one of the biggest dating mistakes retirees make, and my guess is that people don’t want to miss out on the opportunity to find someone special, so they decide to say yes to almost everyone who contacts them or asks them out.

Let’s take my friend, for example. She was so focused on being with someone who was right for her and who was funny, intelligent, and well-mannered that she wanted to give everyone a chance to see if they lived up to her expectations or not.

But what she imagined wasn’t exactly the reality, and she actually came across people who were not her type at all. However, that’s not necessarily a bad thing, because it can help you filter your dating process and give you a better idea of the type of partner you should be looking for.

She also came across people who were a bit too extreme for her or who lied about their age. One time, she went out with someone who mentioned on their profile that they were 62, but when they went out, they didn’t have more than 40 years, and the reason they lied was that they liked older women.

The moral of the story is that it’s best to make a list of criteria you want your future partner to have, as well as a few things for which you’re okay with making an exception, and only say yes to people who fit your description.

Photo by Jacob Lund from

4. Taking things a bit too seriously

Each time my friend went on a date that she thought went well, she would call me to tell me all about it, ask me what I thought, show me pictures of all those people, and even need me to cheer her on when things went badly.

Of course, I was happy that she had a good time on her dates, but I started thinking that she was excited about almost everyone, and I didn’t know how to react or what to tell her. But after a while, she actually realized which people she liked the most, and then things were great.

I still remember one of her worst experiences: my friend is a smoker, and when her date dropped her off, they leaned toward her for a kiss. The minute their lips touched, that person backed down and said that they couldn’t date a smoker, so goodbye.

Yes, she understood that some people simply hate cigarettes and the smell and taste they leave behind, but what was a bit much was that they didn’t even wait for her response and decided to leave ASAP.

If you’re a retiree who’s getting back into dating, my friend and I have some advice for you: don’t get your hopes up on the 1st date unless you know deep down that the person you’re seeing is the one for you.

Other than that, just be patient, because sooner or later, your ideal match will be next to you!

3. Not having a mental checklist

I already said something about a mental checklist on the previous tip, but I can’t stress this enough! It’s very important that you know what you’re looking for. It’s like adding some filters while you’re online shopping for jeans. Instead of scrolling through tens or hundreds of pairs of jeans that you don’t need, you just add the size, color, and style you want, and it’s a lot easier to discover the item that’s right for you.

If you do the same thing in your dating life, it will be a lot easier to find the person who will sweep you off your feet. So what are you exactly looking for in a future partner? I’m 100% certain that your expectations are totally different from what they were when you were 20 or so years old, so really think about it.

Take some time to get to know this new version of yourself before you begin dating again. If you’re having trouble deciding what you want, grab a piece of paper and a pen and jot down everything that comes to mind—it’s both therapeutic and will make your dating life a lot easier and more fun.

Photo by Diego Cervo from

2. Being too old-fashioned

Women have this weird and ancient idea that they should only expect to be invited out and shouldn’t make the 1st step. That was probably right many years ago, but nowadays, things are moving pretty fast, and you shouldn’t wait for someone to hit you up, especially if you’re into online dating.

Be brave, and if you like someone on the Internet, just send them a message and get the conversation going. You don’t have to say something special to make someone interested in you. A simple “hello” is just enough to give off the impression that you’re interested, and if you’re feeling extra courageous, you can even ask them out.

Who knows where things might be going? Just be yourself, and you’ll notice that your dating life will be just great! If you need any tips on how to have fun when dating, I have an amazing book for you to read. Trust me, it’s going to spice up your dating life, and it will turn you into the greatest partner ever!

1. Rushing

This isn’t a mistake that only retirees make, but it attracts more complications when people who do this have recently been divorced. I get it. You went through a tough breakup. You noticed that you and your partner could no longer function as a couple, so you decided to part ways and look for love and happiness elsewhere.

Now you’re back in your dating game, and you’re hoping to find someone who’ll make you smile and giggle each time you see them. But what’s the proper time to wait after a divorce to start dating again? That is entirely dependent on you and how you ended things with your spouse.

For example, if you’re feeling empty, tired, and want to cry once a day, remembering how your life was before the split, that’s a sign that you need to focus more on yourself. Analyze your situation and focus on your friends and family, your home, your hobbies, and the things that generally bring you a glimpse of happiness.

When you’re back on your feet again, feeling powerful, happy, and worthy of only good things, that’s when you know that you’re ready to get back into dating!

…Are you into online dating? Here’s an article you don’t want to miss: Online Senior Dating: Avoid These 12 Mistakes at All Costs!

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