rules of online dating

These are my 10 rules of online dating based on tons of hours spent online with clients for over 25 years. As you read over them, note down how many of them you follow, then score yourself at the bottom.

Here we go:

Fake It Till You Make It

Self-confidence is attractive. So, you’ve been widowed or divorced and not been on a first date since your 20s or 30s? No time better than the present.

Practice Makes Perfect

You won’t get it right the first time around, but that shouldn’t surprise you or wipe your motivation. It’s tough to find yourself online, staring at the 318 potential men that showed up in your search. Instead of being overwhelmed, spend 30 minutes, choose 5 people, and send 5 messages.

Your goal is to get used to sending messages, not to try to attempt to recognize which profiles would score a “10.” After all, how do you know from a dating profile what a man (or anyone) is really like? It’s a message, not an invitation to marriage. It’s an opportunity to see how they respond and what type of info they may not have included on their online dating profile. No commitment involved!

If You Always Do What You Always Did, You Always Get What You Always Got

Change it up. Be bold in your messaging. Think quirky (not weird) and unique. Take this Dating Quiz as it may show where you are going a bit in the wrong direction.

Do a Photoshoot with a Friend When Going Out

Have a friend snap a few new photos of you this weekend when you’re out at dinner, golf, pickleball, cocktails, etc.

Then use this as the primary photo. You’ll be shocked – the people who scrolled by you in the past, may take another look at your refreshed photo. And always date your photos – men will appreciate knowing what you’re going to look like when you show up on your first date with them.

Below is a photo of a client who had a friend snap the shot last Friday night to celebrate her 60th birthday. Of course, I added it to her online dating profile and men have commented how fun and happy she looks. And yes, it’s led to two upcoming dates.

Take a Goofy Picture (Not a Selfie)

This makes people laugh. Also, instead of writing in your online dating profile, “I have a great sense of humor,” let your photo show it.

You would be surprised at some of the goofy photos that have helped my clients pick out potential dates. For instance, what would you say about a Harvard-educated 64-year-old attorney juggling 5 pomegranates with a zany look on his face? Of course, the rest of his photos were more “corporate,” but my client immediately messaged him, and it resulted in a fun date.

No Doomscrolling

This is dangerous to your mental health – seriously! When you go online with a negative attitude, what do you think you’re going to get? Nothing.

As an aside, here’s a text I received on Valentine’s Day which made me happy:

Commit to Three Months Online

Put a three-month limit to your first online dating try. Why? Most clients want to quit after week one or two. And guess what? The magic starts around week three. I’m not kidding. I’ve been doing this for over 25 years and over 65% of my clients are now in relationships. Did it happen the first two weeks? Rarely.

Keep It a Secret

What? No, you don’t need comments from the peanut gallery. Your friends, family and acquaintances can be a major negative force. And, what do they know about dating in the 2020s? It has changed so much from the 1980s!

Your Mantra: You Are Not Too Old to Date and Be in a Happy Long-Term Relationship

You all know about 2nd Acts in business. Angel Cornelius started Maison 276, a skin care company, at age 60, and by age 63 was featured in Oprah’s magazine. The founder of Sixty and Me, Margaret Manning, started this successful publication in her 60s. All entrepreneurs hit some bumps in the road – just like you will in dating. But if the bumps lead to something lovely, it was all worth it!

It Only Takes One

It doesn’t matter if you live in densely populated NYC or in the middle of horse country in Montana – there are good singles in every part of the country. If I had a dollar for every female client who asked me “Aren’t all the good men taken,” I’d start a new charity.

It doesn’t matter if you are on a dating site/dating app and there are 200 men meeting your criteria or 20 – you only need one. And from where I sit, objectively, I see this happen every single week. So, refer back to number 7 and give it a go with 3 months, 2 hours per week and don’t make this your full-time job!

What’s Your Score?

So, I invite you to score yourself – how well do you follow these dating rules?


9-10: You are rocking it and on the precipice of meeting the right person.

7-8: You are making an effort – keep it up!

4-6: You are half in, half out. Re-commit.

1-3: Take a break. Or hire help. You need some serious accountability.

Oh, you might find this article interesting from Kiplinger this week on online dating: Read Me!

Have a lovely week and don’t give up. I know the saying is corny, but there is a lid for every pot.

Let’s Have a Conversation:

How did you score on the 10 Online Dating Rules quiz? Are you lacking in motivation, accountability, persistence or something else? Have you given up on online dating?