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5 Online Dating Messaging Mistakes

Poor online messaging skills are cited by both The Wall Street Journal and major research companies as to why singles fail with online dating. I wholeheartedly agree. Since about 75% of my time as a dating counselor is spent online coaching clients on picking the right match…and crafting the right message to engage and convert this text to a real date.

Yep, I actually teach message writing---and it’s a bit of an art. It’s probably my favorite activity I do with my clients---as it’s flirty, bantering and we laugh constantly. It’s fun…not work.

Online messaging is the number one item that frustrates singles…and makes them feel like online dating is drudgery, a full-time job, a time-sucker. Or just doesn’t work. Get the right banter going online two things will occur: Results and Fun!

So, let’s get on with these basic assumptions first*:

· You are on the right dating site/app for you

· Your dating profile/prompts are engaging and exciting

· Your photos are recent, fun and show you in various activities

Here we go with messaging mistakes:

1. Copy and Paste Ok, we know what you are doing. The message is unoriginal and generic and could fit 99% of Earth, Mars, the entire galaxy’s singles! Examples: “wow, you are beautiful”, “Hey, how’s your week going” to the blunt “I’m interested”.

In what?

Working with a new lovely 48-year-old from Marina del Rey, CA client yesterday, we had some laughs and shocks. Being new, she had over 50 likes with many messages. Here’s a real one: “Hey, Marisa, your body is just amazing. I would lick the floor you walk on….”. Oh, this guy got worse. Luckily this isn’t the norm! Our fingers were sore as we took turns hitting the Block/Delete button. BTW, after our one-hour coaching call together where we sent over 20 messages on men WE searched out---we did get a bit cheeky and humorous! In a gracious way, of course, and that paid off this morning for Marisa. (Outcome: Eight of the men had positively responded by this morning. She is having lunch today with a man we reached out to). Yay!

2. Guys, this does not work: “Interested. Read my Profile”. Hmmm, what do you think women do? I teach my clients in under 90 seconds to scan a profile and scroll quickly through the photos. Result? Either a message back or delete. No saving for later. This is a fast game: cyber dating. BTW: My advice would be to skip this person. Abrupt. Brusque.


Want results in your love life? Set up a free 15-minute call with me—I’ll let you know if I can help and if we are a good fit! Click here!


3. Ladies, A message is not a wink, heart, like, smile. It’s lazy. A copout. And men’s number one complaint. You just threw the ball in their court.

4. Trying too hard. You be you. There’s no right message. Some of my clients are outgoing, some reserved. The recipient of your message appreciates a sincere message. Here’s a couple examples from 2 different clients that we wrote yesterday and Thursday, as yes, once again I was coaching online dating messaging:

“Rob, I like that the ocean centers you---feel the same way. Yoga too. Must say your handstand on the beach is a WOW! What’s your tennis level? I started a bit late in life but totally addicted---how about we continue chatting over a drink Saturday or lunch Sunday? Warmly, Leah”

(Outcome: having brunch Sunday)

“Simon, OMG---Ping-Pong! I’d love to play though never have. Think my tennis game or yoga will help me with Ping-Pong? Lol Your puppy is sooo darling—How about lunch at Lazy Dog Saturday or Sunday? We can sit outside with our pups—Kelly (Outcome: They are meeting today)

5. Messaging about Work.

Ok, I write from practice, not theory. This morning a 53-year-old male client (very successful) in NYC was sharing his Hinge app screen with me via Zoom during a coaching call. This was a check for me on his messaging style. I nearly fell asleep reading the text chain where one potential woman and him texted back and forth about their professional life…. until the text chain just petered out. This is about dating---you are not texting an executive recruiter!

I was so happy to move onto his other text chains---and see he had a date scheduled for tonight and one for next week. With fun women. One was talking about studying sharks and photo of her swimming with sharks and another in a shark cage off the coast of South Africa. Another asked him “what would your friend group say about you”. I thought that was a brilliant question!

Remember, the only reason you are texting and messaging is to get to a first date! There are no set number of messages until you take it to a facetime call or a phone call. You can totally skip the call. Go straight to the date.

As a dating coach, I strongly urge my clients to text no longer than 2-5 days. Chemistry only happens in real life. If you are more of an introvert or shy, you will get over this very quickly once you’ve gone on 3-5 first dates. I promise. I do this every day. For 25 years. 65% are in relationships. It works!

Happy Messaging!

Love & Laughter,

Andrea McGinty Founder,

*Basic assumptions: You had a dating expert/dating coach write your dating profile, vet your photos and choose the correct sites for you to be on.

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