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

5 Crucial Online Dating Pointers

By Andrea McGinty October 11, 2025 Dating

I’ve seen so many intelligent singles make simple errors that hamper their chances with online dating. Before you say, “Online dating does not work,” (it does) or “It will not work for me,” (why not?) or “My friends tell me horror stories,” (believe me, they are doing something wrong – it’s them, not the app/site), here are some things to think about:

An Error-Free Profile

When you create your app profile, make sure it is grammatically perfect with no mistakes. Yes, people read these, and if they see you using “there” and “their” wrong, they very well may skip right over you. My recommendation: Write it in a word document first. Then run spell check it.

A Unique Profile

Short and sweet is what you’re aiming for. No one wants to read a long monologue. Yesterday, working with a client, we saw an attractive, accomplished man who used two paragraphs to describe how wonderful his wife had been. He listed all her amazing traits. However, she had passed away 5 years ago, and while we felt for this man, he was obviously not ready to date. He probably wonders why he is not getting any responses!

We bumped into this profile also that I thought was succinctly and cleverly written by a man:

“YES: vanilla, rosemary, Buenos Aires, humility, Barnes & Noble browsing, bourbon, cilantro, dogs, generosity, bikes, empathy, skates, skis, boats.

NO: beets, videoconference dates, whining about online dating apps, Red Wings, selfishness, arrogance, snakes.

I can’t grow a bougainvillea to save myself. It grows like a weed here and I can’t keep it alive for 10 days.”

Ok, there was a bit more to his profile but he clearly and with humor got across his likes and dislikes. Of course, I had my client message this man!

Messages

If I hear one more woman tell me the man should reach out first, I’ll lose it! No, no, no, is my emphatic answer. Men love when you make the first move. Men love when you are not afraid to reach out first. In fact, they are bummed if they have to do all the first-time messaging all the time. Almost as bad is when they receive a like/heart/wink with no message.

This is the area where many singles fail. If they do send a message, it can be one of two big mistakes:

  1. It’s a short generic message.
  2. It’s a 3-paragraph novella where you get cross-eyed by the end with way too much information. Just like a long profile, nobody reads long messages.

This is my favorite area to coach clients on! Here’s how it goes: We are on the site/app together, and for the first few weeks of coaching, I type the message, then read it to my client before hitting send. Sometimes I hear a sharp intake of breath followed by “What? Are we really sending this?” Yes, and I explain why!

Most of my clients quickly get the hang of it, though I do wake up to a few texts each morning with screen shots saying, “Help, how should I respond to this person,” which I must admit, I love crafting messages that get responses!

The Phone Thing

Pre-date, why do you need to chat on the phone? Here are the issues with that:

  1. A 45–60-minute call gets people all excited. They have deduced they have so much in common with the other person, and their first date expectations have risen astronomically. Very few dates can measure up now.
  2. A short, awkward call and no date ensues. This is a bummer because the other person may just not be good on the phone – perhaps a bit reserved, shy, etc. This could have been the right person for you!

The only time I encourage a phone call is if there is significant distance. Let’s say you live in Los Angeles and he lives in Laguna Beach. The traffic is rough! Then I encourage a 10-minute call first. Here’s how I recommend that you phrase it in a message: “I’m totally interested in meeting you. Let’s do a 10-minute chat to see if we’d like to meet in person. My number is XXX.”

This way, we have put in place two boundaries: the call will be 10 minutes and the reason for the call is an in-person date.

You live within 20 minutes of each other. Go on the date. It’s coffee or a drink. It’s an hour. Let’s stop with all these time-wasting phone chats. You would be surprised, but people do complain about meeting someone for a short date. Why? The response I get is, “I have to get dressed.” Well, get dressed and go!

Your Photos

Nobody – yes, nobody – goes to your profile first. Photos make or break you.

If you are serious about online dating and going on good dates or perhaps beginning a relationship, 5-6 great photos are a necessity. And by that I do not mean filtered, air brushed, highly edited photos. I just mean you at your very best. And current – as in from the past year. And what you will look like when you show up on your date.

I vet client photos. In my experience, about 50% of my clients already have online-ready photos. The other 50% I recommend they go to photo service that is reasonable, takes two hours, and they turn around the photos to us within 48 hours.

And the type of photos? After your Zoom call with me, I give you a photo shot list. And it’s not your LinkedIn or fancy, boring in-studio poses. It’s you – in action! What do you enjoy? That’s what we need captured in photos. I had an NYC Wall Street type juggling as he enjoys it. Plus, he bowls. (It seems no one bowls and that grabbed a bit of attention). Not the stereotypical private equity guy, right?

I hope this helps you a bit on your search to a great next date.

Let’s Have a Conversation:

Where do you need help with online dating? Do you think online dating will work for you? If not, why not? What do you write when you initiate a message to men?

Subscribe
Notify of
guest
11 Comments
Newest
Oldest Most Voted
Been there

No more for me!
My last date was 40 lbs overweight only which wasn’t a deal breaker but wasn’t a turn on either but when I saw his ankle monitor as I was getting into a cab…
I much prefer the company of my cat.

Been there

I’m pretty sure much finished with on line dating!
The guys my age (69) are amazingly vain and don’t want a wiser woman but look for 10 yrs younger or more.
My last date was 40 lbs overweight only his face was in photos on profile and as he stepped out up the stairs to the coffee shop I saw an ankle monitor…what’s that for ? I asked….”oh my ex got me for stalking “
Yikes!
I prefer my cats company at this point.

S Bryant

Men don’t read profiles, they “like” by the photo. I’ve had many experiences it’s obvious they didn’t.ie: politics.

Tessa

After a few years of “off n on” online dating & having a few breaks in between (& telling myself that id had enough of it), i decided that all my experiences were worthwhile, and i learnt so much about myself as well.

I wish that the really lovely man that I met on one of my dates hadn’t his only adult child tragically pass away. He had different colour skin than me, different background than me, was intelligent and warmed my heart from the start. He told me he had a “larger dog” from the start, but what he forgot to mention that this dog was the size of a pony and on our first visit the dog ripped up every plant in my yard in 30 mins flat. Then he told me he was about to adopt another large dog as well.
Our second date was at a dog free beach, and i watched in amazement as his lovely pony sized dog pulled my date along by the dog lead like my date was skiing!
Then his dog managed to break the leash and within minutes was destroying a beautiful garden nearby. The last time I saw this lovely man was when he was running barefoot down the road calling out to his beloved pet, while listening to the nearby gardens owner yelling out in horror! I smiled and knew at that moment that i couldnt and wouldnt go any further with online dating business.

For me IF i was going to meet someone, i knew it would be the natural old fashioned way. So i went out and did things that “I” enjoyed doing without the pressure of dating a stranger.
So i joined a bushwalking group where I was with like minded people. Met and made friends with a lovely lady, who just happened to be in a relationship with a man she met in a over 60 singles group.

The 2nd week after having dinner out with a group of decent men and women i met a nice friendly bloke. We made friends and are still friends 9 years later. We do live together due to financial restraints. We do some things together and some apart.

We have each others back & im so glad I tried ‘a different way’. Im no longer lonely and unsupported.

Online dating can bring us much wisdom as we leatn who WE really are as well.

PAMELA J BLOME

I have been on and off online dating for at least 10 years (after becoming a widow). I get plenty of attention through my photos and wonderful comments about my profile. My problem is, that all I seem to attract are the wrong men: ones that look old, don’t take care of themselves, etc.. I’m at a loss as I love being in a loving relationship but the frustration is overwhelming. help

andrea

Hi Pamela—I feel your frustration and many people come to me frustrated and discouraged. I’m thinking it’s either the wrong site or the type of messaging you are doing. When I work with a client, we ignore the likes and I put in algorithms and search filters so we identify the right types of men you are looking for. Then we reach out—-over 60% of my clients are in relationships so I am a big believer in online dating—done right. Perhaps you can book a free 15-minute call with me and we can chat about what you’ve been doing and a better strategy. My widows have had much success. You can sign up at https://www.33000dates.com I’d love to help! Warmly, Andrea McGinty

The Author

Andrea McGinty, founder of 33000Dates.com and It's Just Lunch, has spent more than 30 years helping people find lasting love. Her proven strategies have led to 33,000 first dates and over 10,000 marriages. Author of the bestselling 2ND ACTS and featured by Oprah, Forbes, and The Wall Street Journal, Andrea believes: Love isn't luck. It's strategy.

You Might Also Like