Dating Rules
How to win the dating game (Without losing yourself)
Welcome to the New Dating Landscape
Remember when dating meant waiting by the phone for a call? (The princess phone with the LONG, tangling cord?)
Or when meeting someone happened organically through friends, work, or social events? (The blind date…)
Fast forward to today—welcome to the world of swiping, ghosting, and texting etiquette.
If you're like me and re-entering the dating scene after a long-term marriage, you may feel like you've landed on a different planet.
Don’t worry! The good news? You have more power, confidence, and wisdom than ever before.
The challenge? Learning the new rules so you can date on your terms without losing yourself.
Dating Today: What’s Different?
Dating in your 50s and 60s is not the same as when you were younger. Here’s what’s changed:
Online dating is the new normal – Apps like Bumble, Match, and OurTime cater specifically to mature daters.
Don’t make the mistake I made signing up for a random other app because I didn’t want to encounter my Ex on the app. It was for meeting European men. I wasn’t really ready to meet someone here who I would have to actually meet in person. I liked the idea of texting with a stranger. The problem:
I get emotionally attached to people rather quickly.
The photos are great, but they are hired models to pose—not real people looking. Then they hire people to respond to the texts.
I was totally snookered. Don’t you be as well. Stick to the main apps for women of a certain age: Match.com and Bumble. There are some on Hinge, but I didn’t have any success with that app.
Women make the first move, too – Unlike in the past, you don’t have to wait for a man to ask you out.
OK. Don’t laugh too much but I was really unsure about the whole dating thing. I am a very social person, but a bit shy. So I took a course in online dating. Just a little $27 course to see what I could learn.
One of the first things she said was that women make the first move. Of course I wanted to be the chosen one instead of the chooser… but I got over myself. I would read the profiles and inevitably, as anyone who knows me would know, I would need to make some sort of comment. I can’t keep myself from commenting. Which is perfect for online dating! One man was a big fellow and he was wearing a Santa shirt. (In fairness, it was Christmas time.) Comment. Another fellow said he liked board games. Had to know which ones. Another fellow liked hiking. I wanted to know his favorite hikes. Several men said they love good food, so I asked what their favorite neighborhood restaurants are… Simple, easy, conversational comments. The key is to give the guys an easy way to respond that’s a basic no brainer response.
If you comment, inevitably they will check out your profile and decide if they want to answer you. Some do. Some don’t.
You can’t take this personally (although of course I did!). You just keep going. As they say, (who are they anyway?) It's a numbers game.
So go through your profiles, click who looks interesting to you, read their profile, find something worth commenting on, and do it. Then keep scrolling. Don’t sit around and wait for a response.
Casual relationships are more common – Not everyone is looking for marriage; some just want companionship or fun.
This is an important note. When I started online dating, this was my mindset: I am practicing. I am not looking for anything in particular. I am looking to practice dating.
I started with people with whom I would feel comfortable. I had one coffee date, 3 wine dates, a lunch date, and an evening date. And guess what. The more dates I went on, the more comfortable I got!
Remember– you are nervous–They are nervous too! It’s a two way street! So be kind and generous with your stories and self.
Texting is part of courtship – But beware—flirty texts don’t always translate to genuine connection.
I fell into this trap. Flirty texting was fun. But after a few weeks, when the guy didn’t want to get together after I made an offer, I figured I was wasting my time. So I blocked him and moved on.
Why, you might ask? Because you need that space and time for people who will take action not sit around comfortably texting from home. Adults take action. Wimps sit on the sidelines and comment on everyone taking action but don’t act themselves.
The New Dating 'Rules' (That Actually Work for You)
Forget outdated dating "rules" that don't serve you. Here are the new ones:
Be proactive, not passive – If you see someone interesting online, don’t hesitate to reach out.
Date multiple people at once (until exclusivity is agreed upon) – This helps you avoid over-investing too quickly. (Which happens to me– I get over-invested way too fast…)
Set clear boundaries – Want commitment? Say so. Not into casual dating? Make it known.
Texting is a tool, not a relationship – A person who texts well but never makes plans is wasting your time. NOTE THIS AGAIN! Wasting your time, headspace, heart, etc.
How to Date Without Losing Yourself
The biggest mistake women make after divorce? Forgetting that dating is about you just as much as it is about them. Here’s how to stay grounded:
Know what you want – Are you seeking romance, companionship, adventure? Define it before you start dating. This is an important step not to be missed. It may evolve over time but be clear.
Trust your instincts – If something feels off, it probably is.
Beware of love bombing – Some men will shower you with attention only to disappear later.
Red flags matter – If he avoids personal questions, is "too busy" to meet, or is hot and cold, move on. This is an important note. I met one guy who was lovely, but we had a hard time getting together, we met in an odd location, at an odd time. I mentioned it to a friend and she did a search. From his photo on the app, she discovered his real name, and that he had been married since April of that year! He was a newlywed and still apping! Which I of course found appalling so I immediately blocked him.
Which brings up the topic of checking out people. You can copy their photo from the app and put it into Google lens and do a search just to make sure they are who they say they are. I like to believe people act in good faith. I like to trust. But it’s good to have this ability in your backpocket just in case.
Online Dating: A Survival Guide
Navigating online dating can be overwhelming, but with the right strategy, you can thrive:
Choose the right platform – Bumble gives women control, OurTime caters to 50+, and Match is a classic choice. I recommend Match for the most choices. Many are on both Match and Bumble.
Craft a strong profile – Use recent, flattering photos and write a bio that reflects your personality and values.
If you want help writing your bio, I highly recommend Chat GBT. I prompted Chat GBT ( you can use the free version) by saying I was in the process of getting divorced, am 65 years old, and need help writing a profile for Match.com. It said to answer these 6 questions, and it would write a profile. So I did that. And honestly, I’m a decent writer, but it’s hard to write something worthwhile about yourself. Chat did a great job capturing my personality. I made a few edits and adjustments and posted the profile.
When I wrote my first profile, I got a few hits, but honestly, I thought I would do better.
After Chat rewrote my bio, I got seven hits the first day! It made a huge difference! So give it a try. You can email me if you want me to help you. It’s really quite fun!
Spot the scammers – Never send money, watch for vague profiles, and trust your gut. Read this one again and brand it into your brain. If the guy doesn’t have a picture, skip. If he can’t take the time to write a profile, skip.
Winning the Dating Game (Without Stressing Over It)
Dating should be fun, not stressful – If it feels like work, take a break.
Not every date has to be "The One" – Enjoy the experience, even if there’s no love connection. I made a few nice friends!
Stay open-minded – Your ideal partner might not fit your original "type." This is a good point! The man I connected with is the exact opposite of anyone I thought I would date. But he makes me laugh out loud and plays cribbage with me. No one else did that! So keep your mind open.
Most importantly, enjoy the journey!
Of course, only meet in public spaces like coffee shops or wine bars or something like that. Never let yourself be vulnerable.
Notes:
I was always hesitant to give out my phone number. I kept things on the app. I gave my number once we had a meeting place and time so we could check in. I was glad I did this so I could easily block someone if the tides changed.
Always tell a friend who you are meeting when and where for safety reasons.
Of course, only meet in public spaces like coffee shops or wine bars or something like that. Never let yourself be vulnerable.
Be honest in your presentation of self. If you’re 65, don’t show photos of you as 35! Several guys complained to me that women did that. Men do that too. Be proud of who you are and own your age. You don’t want to be accused of false advertising.
When I first got on the apps, it seemed like everyone was interested in hiking. So I invested in a pair of hiking shoes. Then NO ONE was interested in hiking, they were all golfing. I am not investing in ANYTHING about golfing.
At first, everyone had something that turned me off… They showed themselves skiing and I don’t ski… they were in a boat and I get sea sick… they were golfing and I have no interest in golf… they talked about watching sports on TV every Sunday… I have no interest in sports on TV… So basically I swiped every guy off and was left with NOTHING. Moral of the story: be a little flexible. They are trying to show themselves in a positive light. They probably have a life beyond those photos. And actually when I asked a guy about that, he said he WANTED to ski but hadn’t actually skied in several years. So the photos are pretty aspirational. Keep an open mind. Just get out there and practice.
From the little course I took, I also learned there are 2 pivotal points: if you make it dating the same guy past 3 weeks, that's a hurdle. If you make it past 3 months, that's the second big hurdle. Don't put the cart before the horse. Enjoy yourself.
Discovering YOURSELF
Dating after divorce isn’t about proving anything to anyone—it’s about rediscovering yourself while opening the door to new possibilities. The dating rules may have changed, but with the right mindset, you can absolutely win the game without ever losing yourself.
What’s Your Experience?
Are you back in the dating world? What have you learned? Share your funniest, best, or most surprising dating moments in the comments!