Sometimes we don't find true love until later in life and that's fine!
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Singles over 50 may need a little advice when it comes to dating online. Plenty of seniors have never experienced anything like internet dating before, however, most have at least heard about free online dating sites for seniors.

As a matter of fact, I bet most of us didn’t have a clue that we’d even consider online dating for singles over 50 as an option. But what do you do when you really don’t get out much anymore? When you look at it with an open mind, it’s a great idea! However, not everyone has this perspective at first. 

Over fifty dating or as someone who’s recently divorced or widowed after 30 years, dating again can be scary. On the other hand, it could be you’re finally ready to settle down but haven’t found anyone that special.  

When I was a young girl, the elders told me I wouldn’t find a good man in the club, and to go to my local church. Well, sadly, [for me] church turned out to be a bust. Each and every attractive, good man in there was taken [sigh]. The next step was online dating. It was free so I had basically nothing to lose.

I must admit at first I felt a little awkward browsing dating sites for over 50 and all, but then I noticed some very attractive women on these websites in search of a date as well. This made me feel a lot better about signing up.


In fact, I began to enjoy dating online. It gave me a sense of control I hadn’t felt in a long time. Meeting other people on the internet who were serious about finding love was comforting.

It wasn’t long after I completed the senior dating profile I received a few emails and winks from guys. I chose the personals I thought was right for me and started communicating with them. Went on a few dates and now, I’m one happy camper. Yeah! It was just that easy.

Read more: Dating After 50

In light of my success, I thought I should share some online dating tips for singles over 50.

Singles Over 50, Review Your Wants and Needs

What I really liked about these senior dating sites is the ability to search the profiles and pictures to find out if we could be compatible. I knew what I was looking for in a mate, so that narrowed the search to a specific group.

I enjoy traveling and eating authentic foods based on a particular culture. I wanted a companion for these dates who was around my age, who had a vehicle and of course, some cash.

I mean, I’m over 50. I don’t want to pick my date up and I certainly was not paying for his meal. Eating out can be expensive.  I know!  I spend too much of my own cash eating out but it’s what I like to do and life is too short for me not to enjoy the fruits of my labor, right? Right! 

What I needed was a secure and confident man, someone who could make me laugh and to have a stimulating conversation with. What I got was a confident man but he had a few insecurities about dating sites for people over 50 as well.

The Jamaican man was indeed funny and interesting but he didn’t own a car. He said he lived previously in a busy city where public transportation and biking was the best way for him to get around town and now he’s retired, he still doesn’t have a need for one.

He uses the same bicycle to get around my small town and he’s in perfect health mainly because of it. And it shows in those legs of his. Ha! Who am I kidding? You would love the rock solid guns and abs on this man! So, with this in mind, be lenient about your wants and review your needs.

Be the One Who Starts the Conversation

If you see someone you like, send them an icebreaker. Don’t wait for them to come to you all the time. Often, older men are like us and this is their first time on one of these dating sites for over 50s. They are a little nervous, too, so take the ball and bounce it.

If you’re old school like me, women were taught the man should ask a woman out, but this notion is a little outdated especially for independent women. [By the way, they have dating sites for professionals over 50.] Nonetheless, I was also told a closed mouth is never fed.

Having said this, if you want someone, let them know. They key is not to make a nuisance of yourself. Once they have the ball, they should bounce back. If they don’t, wait a little while and nudge them again.

They could be busy or maybe they aren’t active members anymore. After the second attempt, if they still don’t respond, take your ball and move on.  There are plenty of available men online dating, looking for singles over 50.  

Singles Over 50, Keep it Positive

While we want someone we can talk to, we shouldn’t divulge our dirty laundry during the initial stages of online dating, on the first date or even on the second date. This is assuming you like them well enough to take the relationship offline and actually meet them face-to-face.

By the way, it’s still in bad taste to trash your ex or your job right away no matter how comfortable you feel with your potential mate whether you’re in person or in the chat room. Keep the conversation light, impersonal and cheerful. There’s a time to discuss how pitiful they were, but this ain’t it. 😛 

Where to Meet Singles Over 50

You know the town like the back of your hand but suddenly, you don’t have the slightest idea where to go. You don’t want to go to a bar and scream your conversation. Dinner and a movie is an idea but it’s so predictable. Want to try something new and different for a change?

Paint and Sip is a popular idea these days. It’s where you learn to paint while sipping on some savory wines. You get to keep your paintings so this would be an amazing reminder of your first date together. Don’t like that idea?

How about a game of golf, a drive to the country, stroll the vendor’s booths at a craft show, flea market or farmer’s market? There are plenty of places in your area that don’t require a lot of money and are fun. Be flexible, though.

What to Wear on a First Date

Normally, we know what to wear and how to act, but all of that knowledge has gone right out the window. You’re anxious and I get it. You look in your closet and there’s absolutely nothing to wear among the hundreds of possible outfits.

Ladies, listen, it’s just a date. No matter where you’re going, you should be comfortable. My best fashion advice is not to wear anything overly revealing or too churchy. Put on a pair of jeans, a nice blouse, and comfortable heels. Your best dress is style and class.

There will be plenty of time to put on a little provocative dress but until then, let his imagination run where no man has gone before. I know most of you singles over 50 know this, but some of us… ugh, still need to hear this.  smh… okay.  🙄 


Don’t Make Assumptions

So, you guys are actually dating now and it seems to be regular. It’s clear he likes you and you like him. That’s great news, but here’s the thing: you’re dating and that’s all. You’re not a ‘thing’ yet until you discuss relationship goals and expectations.

What I’m about to say is totally for singles over 50, so you know what I’m talking about. It’s not a relationship until you both agree it is. Don’t assume you’re monogamous when you’re not. So until it’s mutually decided on, it’s okay to see other people or at least mingle with other singles.

Last Online Dating Tips for Singles Over 50

Rashaud Young
When you get to be my age, and you’re dating over 50, you kinda know what you want.

If you’re thinking about joining a free senior dating site, have fun. Take your time and don’t let anyone pressure you to take it offline. That is the idea, but you don’t have to do it if you’re not ready yet.

Put some effort into making your own profile and make sure your profile picture is current and shows your personality. Decide on what you want and what you need but they should be realistic expectations.

At our age, we know what works for us and what doesn’t but don’t discount a man who just turned 50. And ladies, I want you to know I’m feeling highly religious right about now. [haha! Don’t hate.]


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