sixtyandme logo
We are community supported and may earn a commission when you buy through links on our site. Learn more

Don’t Give Up Dating Over 50: 10 Ways to Connect with a Guy Who “Clicks”

By Shirley Goldberg July 22, 2023 Dating

You’ve gone on 14 first meets and you’re done. You’ve had it. This online dating thing isn’t working. It isn’t working and you’re fine with that. You’ve got a life – a great life. Friends, grown kids, grandkids; you love hanging out with them. You love the garden, your work, the occasional weekend away.

You don’t need a man.

You Are Stronger Than You Think

Of course, a man would be nice. But. He has to be the right man.

You’ve tried. The result? Meh. Your daughter’s favorite word, as if meh describes a person. You met 14 men, and got one second date. Yup, Number Ten called and you went out with him again, so it counts as a Real Date.

But he didn’t call for a third date.

And now you’re done with online dating.

“It’s enough to make you wonder if there’s something wrong with you,” says Jill Whitney, a licensed marriage and family therapist. She reminds her clients they have strengths and positive qualities.

Write It Down

Whitney suggests that if you tend to forget your good points, make a list. Take a piece of paper and write down everything you’re good at, and all the ways you’re a good person.

If that’s hard for you, ask friends for suggestions. Once you get going, it’ll get easier. Keep the list to review at times you’re feeling discouraged about dating.

“It’s okay to take a pause from online dating at times,” says Whitney. “It takes stamina to keep putting yourself out there, which means you’ll need chances to rest and restore yourself. Give yourself permission to step back.”

She suggests to do fun things with friends, clean out your closets, do jigsaw puzzles, go to the movies. Then, when you start to feel like getting back out there, you’ll have more energy and bring your best, happy self to the process.

Talk to Everyone

Use online dating as a back-up to meeting someone new in real life, rather than concentrating all your energy on a dating site. 

No matter where you go, chat with people. Sure, you’d rather meet someone at Home Depot or in the supermarket. Or at that cute place downtown where they have a band on a Friday or Saturday night. Or at a Meetup.

Or maybe your friends Carol and Danny will introduce you to… a friend of Danny’s? (They met online and they’ve only been married three years, so who knows? Danny may have a single buddy.)

Friends are a valuable and mostly untapped resource. 

Don’t Let Your Past Block Your Future

Don’t let your break-up or divorce get in your way.

Whitney explains that some people feel they’re “doomed” in relationships because their previous marriage didn’t work out. “There’s just no truth to that,” Whitney says, because marriages end for all sorts of reasons.

Take a deep look at what went wrong in your previous relationships, including whatever role you played in the problems. Learn from that. Bring that hard-earned knowledge into this next stage of your life, where it can help you build a better relationship this time around.

Be positive. It can happen to you.

He could be right around the corner.

If you never give up.

A Few Real Life Pointers

In my novel, my main character does a lot of online dating, and her best friend, an experienced dater, tells her how tough it is out there. “Get a helmet,” she says. “Strap it on.”

Do you need a helmet? In a way, yes, a metaphorical one.

You need to believe in yourself, that you are worthy of love, and have the self-confidence and life experience to prevail. You’ll want to try online dating when you’re feeling strong and resilient. Don’t try it if you’re going through difficult times or have serious health challenges.

Here are 10 concrete ways to up your chances of connecting with a guy who gets you.

Find New People

Write one new candidate 4-6 times a week. Get a rhythm going so you’re writing almost as regularly as you brush your teeth. If you limit yourself to one or two emails (at the most) it won’t be such a chore.

Experiment with Photos

Post a new photo. Get your friends to take pictures of you riding your bike. Cooking in your cute kitchen. Playing with your spaniel. Or your pet lizard. (OK, I’m kidding.)

You get the idea. Yes, put makeup on for your photo. Wear a hot pink top that makes you think “Hot men will soon be checking me out.” What’s wrong with a little fantasy?

Know Your Best Qualities

Get your friends to tell you what they most enjoy about you. Write down what they say and use it in your profile. Make them go for specifics – none of that, Suzy is a fun person. 

You need more like, “My friends say I can make a meal from dry toast and parsnips,” or “My friends tell me I’m the one they want with them when the elevator stops on the 29th floor, and we’re there all night.” I’m not kidding. These comments are gold.

No Generic Emails

When you’re writing Mr. Cute, personalize your email. Just do it. Yes, it takes more time, but it’s worth it. No one really goes for those generic, ho hum emails.

Learn More About Their Hobbies

Connect to an activity or a passion he mentions in his profile. If there is nothing, why are you writing him?

No Fear of the Online World

Many women fear online dating. Don’t. Tell yourself, “The Internet is my friend.” Mean it, even though it’s corny.

Go for Authenticity

Don’t create a profile of an ideal version of you that simply doesn’t exist. Let the real you shine through – you’re beautiful just the way you are.

Be Proactive

If you come to the profile of a guy you like, write him. Don’t wait around to be contacted.

Here’s an idea. Suggest a walk in your favorite park. Seriously. Write Mr. Cute and be sure to pinpoint the exact corner where you’ll meet. Get a breath of fresh air – so much better than sitting across the table from a stranger.

Keep an Open Mind

Be open-minded. You don’t think he’s your type? He looks dopey in his photo? He’s into Lee Child novels and you’re not? Open your mind, you’ll never know until… well, read number ten, below.

Just Meet

Nothing counts. Except The Meet. Nothing. Emailing/messaging is a start, but that’s all it is.

Let’s Have a Conversation:

Please share your adventures in online dating. Did you wear your metaphorical helmet? What worked for you? We’d love to hear your story.

Notify of

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Inline Feedbacks
View all comments

I’ve tried online dating sites, eHarmony to be exact, and found it to be a total disaster, as well as a ripoff. I’m 65, a widower, male, wealthy and healthy, and I had my profile up for 6 months. I met a couple of women who talked incessantly about themselves, had almost zero interest in me, and others that seemed to want to play messaging games online. I did not renew and won’t be trying online dating again.

The US Census Bureau estimates that each year, out of every 1,000 widowed men and women ages 65 and older, only 3 women (0.3%) and 17 (1.7%) men remarry. I now fully believe these statistics and I can see why.

I get it. Online dating is tough. I’ve had the same experiences as yours. And yet 5X as many men remarry as women. What’s that say, if anything? I’m with you in that my goal is to find a connection, someone to talk to and more.


Part of why more older men remarry and fewer older women do is because there is, to put it bluntly, a surplus of older women because we live longer


Hello, everyone
I have taken an alternative route to online dating after 25 years of marriage. Online dating wasn’t some thing I wanted to entertain. So I have aligned myself with a new friend, who started a silver single group on meetup, she now has over 200 members in her group. I volunteer and
create the venues with our local restaurants & bands for our members to meet. I suggest you get out and mingle with a local singles group Or create your own on meetup. You can’t shine behind a computer!

Shaggy Maggie

Such great advice!! (first meeting:take a walk together!) After many many starts and stops, I met my hubby online, when I was 59. We both wanted to share our lives, and he met my 5 non negotiattbles. (no kids at home, nonreligious, Europe lover, financially responsible, and no shady business).
13 happy years. He’s cute and so decent!

Thanks and congrats! All it takes is one man. I’m happy for you both and thanks for taking the time to comment!


Looks like you left out the biggest thing men are interested in. I just got tired of pretending to be a sex kitten or fulfill his fantasy. Don’t want it. Don’t need it. Intimacy is nice. Being in sync in heart and mind with someone is the best. But that simply never holds any man’s interest.

Interesting viewpoint. I’m thinking on it. Plus it takes me a while to warm up.


But that simply never holds any man’s interest.

Um, no. I expect a woman to take care of her physical appearance, and that includes keeping herself trim and fit. Once that hurdle is passed, I look for intelligence and outlook on life.

I can assure you that older men are NOT primarily interested in female genitalia.

Lee Ann Phinney

I met my new husband online about 18 months after being widowed. He’d also been divorced, then widowed. We were married 10 months later and celebrated our first anniversary this past May. We’re now 66 and 69. I’ve never been happier!


There is a small number of men who are looking for something deeper than just sex, but the problem is having a strong stomach and being able to keep looking through all the garbage

Dawn Harrison Collins

Good for you both how many men did you date before Mr. came along?

Great question. Online dating takes persistence.

Thanks soooo much for sharing your story! Love it and I’m happy for you both.

The Author

Shirley Goldberg is the author of Middle Ageish and Eat Your Heart Out, both romantic women’s fiction with seasoned characters. Her website,, offers a humorous look at living single and dating in mid life. Shirley’s friends nag her to tell them which stories are true in her novels.

You Might Also Like