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5 Online Dating Lessons to Learn This Week

By Andrea McGinty July 25, 2022 Dating

As a dating coach for the past 25 years, I counsel my clients at 33000Dates.com on a weekly basis – from choosing the right dates online, how to write a dating profile, selecting the right site, to how to message men, and how to set up that first in-real-life date.

So, here’s my past week and what my single clients learned:

Lesson 1: You May Kiss a Lot of Frogs Until You Meet the “One”

Carrie, 58, a dentist from NYC, has been my client for the past 2.5 months and gone on 4-5 first dates each month on average. Two weeks ago, she was discouraged – ready to give up. Then, last week, she met Jack, 61, a semi-retired attorney from Brooklyn.

It was instant chemistry – they both love chess, volunteer at an animal shelter and laughed the entire 90 minutes of their first date. She called me excited as he’d invited her sailing on Saturday. A 6-hour date. Date #3 with Jack coming up. It only takes one!

Lesson 2: Text/Message Four Times… Then Stop!

Daniel, 64, widowed, from Boston is a bit reserved, though with a quick laugh. His first 3 weeks with me produced no dates. Were there women he was messaging online? Oh yes! As the two of us (in our weekly session) hopped on the dating site together, and I looked at his conversations, I said, “What, oh no!”

Yes, he was having lovely chats with 4 women – and 5,6,7 messages back and forth. It was time for Daniel to stop chatting and start dating. We immediately sent a text to each, saying, “I’d like to meet you. How is lunch either Thursday or Friday this week?” Problem solved. Daniel is now going on real life dates and happily reporting back to me.

Lesson 3: Practice Makes Perfect

Olivia, 68, from Laguna Beach, Ca was recently divorced after a 35-year marriage. Ready to date? Yes. Nervous? Yes. The most important issue for Olivia? It’s to get 5 first dates under her belt.

Why? The first time you play pickleball or try Pilates, you may be a bit apprehensive. By the 4th time you hit the court, voila, you know what to expect.

That’s no different than dating. As I told her on the phone when she initially called me to see if we’d be a good fit working together, after 4-5 dates she’d be smiling and having easy conversation. She admitted her dating skills which she thought long forgotten were back by date #3.

Lesson 4: Pick the Right Dating Site

When Tim, 55, from Boston called me mid-June, he was frustrated. Hinge was not working for him. I asked him how he’d chosen this dating app, and he told me his 27-year-old daughter suggested it.

I explained how I chose dating sites for my clients: 50% my gut from working with singles for over 20 years (and over 60% in serious relationships) and second from paid research I received monthly on the top 100 dating sites (can you believe there are 1400 sites/apps out there in the US?!) where I look hard at the demographics, ratios of men vs. women, age groups, and more.

Yes, Hinge would be terrific for his 27-year-old daughter. Once we got Tim on the right site, he began going on well-matched dates with women he liked. He recently went on his 5th date with Joanna, a 56-year-old realtor, and my fingers are crossed!

Lesson 5: Engaging, Fresh Photos Produce Results

Jill, a 62-year-old single woman from Chicago contacted me in February after dating became a full-time, dreaded job for her. She was not meeting the quality nor going on first dates through the two dating sites she was using.

After my Zoom call with her, I was surprised. Super cute. Quick smile. Then… she sent me the photos she had posted. While current, they were poor quality, low resolution and most looked like posed LinkedIn headshots. We fixed that fast!

We hired a local photographer specializing in online dating shots, and after a 3-hour shoot, we had photos of her horseback riding (her favorite hobby), on the tennis court, casually walking around DT Chicago and Lincoln Park – fun, natural photos.

Her response rate shot up, her dates increased, she met Brian, 64, and they’ve been dating since April. The photos were fun, and many men commented on that!

My goal is to always make dating fun for my clients and take the work aspect out of the dating equation. Many singles just don’t know where to begin navigating online dating and this is what I love doing!

What dating lesson has proven the most useful in your experience? Why? What dating mistakes are you making and what are you willing to do to fix them?

Let's Have a Conversation!

The Author

Andrea McGinty is the founder of It’s Just Lunch dating service. She sold it and founded 33000Dates.com so she could help singles navigating online dating. In the 2020s, she knows the best way to meet people is through online dating using a professional coach and specializes in singles in their 50s-70s!

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