Yes, it is not only possible, but highly likely! Had you been in your 60’s in the 1990’s, it was a tough go at dating after a divorce, widowhood, or an ended long-term relationship. When I began matchmaking in 1991 in my 20’s, there were really no great options for singles in their 60’s. Then came online dating. As it reached the 2010’s, many online platforms had figured out their niche—demographically, geographically and the over 1400 dating sites/app present today offer many options to singles hitting their stride their 60’s. It’s a good era to be single and looking for love!
Quickly, I realized in the 2010’s, singles needed help with navigating online dating–all aspects from choosing the right site, an exciting profile, engaging photos and how to message effectively and efficiently to land you on that first date. The magic only happens in real life–not phone calls or messaging or texting.

Table of Contents
So, ready to get started? 8 Tips:
1. Adventure
You need a sense of adventure for this journey. There will be nervousness, anxiety, excitement and a whole mix of feelings. Why can’t I just meet someone the normal way? Because this is the new norm!
2. Age is only a chronological thing
Get over that you are 66 or 62 or 71; age is just a number. I have clients in their 60’s that are much more active than singles in their 40’s. Advantage to you—you have the time to date and more flexibility than the younger crowd.
3. 2020’s–not the 1990’s
Back to this point. Men and woman from ages 50-75 have flocked to online dating and there are about a dozen sites that cater to this age group. Had this been the 90’s, what would you have done? Relied on married friends to fix you up on dates? The reality is that they don’t know many singles; frankly, they just don’t get this whole online thing either. Remember, the biggest pool of potential singles you have ever met was college, perhaps grad school, maybe the workplace. Not anymore. 48% of Americans are single—that’s 128 million people and many are online!
4. Stylists at Nordstrom are FREE
What will I wear on my first date or for my photos? Two of my male clients, Jack 61 and Michael 68, recently went to Nordstrom and had a stylist (yep, it’s free) pick out some outfits for them that were both age appropriate and trendy. Gone were the cargo shorts and ill-fitting khakis. Both Facetimed me from Nordstrom showing me their new duds—and they looked great. What a confidence boost we know a bit of retail therapy can make.
5. New Hair-Do/Cut/Look
Time for a change? I remember my mom once said to me the only constant in life is change and I better get used to it! Savvy mom. Yes, ladies, a trip to maybe a new hair stylist could be the key. While I’m absolutely not a proponent of heavy makeup, all the beauty counters offer free makeovers—just tell them you are going for a natural look that can go from day to night.
6. Don’t overshare your new adventure with friends/family
Ok, talk about the negative Nellies. You’ll hear everything from “Oh I tried online dating and they were all weird and it was horrid” to “Oh, you’re not desperate—why would you engage in this?”. Let me be direct: they have no idea what they are talking about. Working with my clients online for over 50 hours a week, being on the sites with them, I can tell you there are “normal” and “awesome” men and women online. I’d say that about 90-95% of them. And as to that old theory that men in their 60’s wants women in their 30’s and 40’s—wrong. My experience in 30 years is that 80% want a woman around their own age.
7. Hire a Pro—Make it Easy
I highly recommend hiring a dating coach. Why? She will be your cheerleader, be honest and graciously direct with you (unlike your best friend), know what works, choose the rite site for you, write your profile, select exciting photos of you and help craft messages to get you out on those first dates! After 4-5 first dates, you will feel so comfortable dating again. Plus, she gives you some accountability too!
This is a great video to watch about 9 Questions to Ask When Hiring a Dating Coach—Click Here.
8. First Date Topics
Keep it light, friendly, and positive. Easy topics are where did you grow up, movies, books, family, interests, etc. A first date is just….an audition for a second date. Nothing more so dial down that pressure. No talk of exes (yes, we all have them), acrimonious or amicable divorces, horror stories about dates, you can’t believe you are doing this (way to make them feel weird as they are doing it too!), and no negativity. Current events are always interesting—as long it’s not about divisiveness and politics. Shy away from that one. We are all sick of it. Your favorite holidays, family traditions, tennis, yoga—all safe and informative topics!
I have done this for over 30 years—and over 65% of my clients are in relationships as I helped them navigate the ins-and-outs of online dating. That makes me so happy; it’s why I do what I do!