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5 Online Dating Lessons Learned This Week

the nightmare that is dating and texting

As a dating coach for the past 25 years, I counsel my clients at every week ---from choosing the right dates online, how to write a dating profile,  selecting the right site, to how to message potential dates, 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:  “I’ve been on over 50 dates in the past year and there is no one in Jackson, WY”

Said Tara, a 56-year-old professional.  Well, after seeing the sites she was on, and her dating profile, I could see why.  Within 2 weeks, several good dates appeared like magic!  An objective eye can make a huge difference.  She calls me now “the fixer”.


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, 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.  Stop, Daniel.   We immediately sent a text to each “Wow, 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.

how to stay positive after a string of bad dates


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 or studio, 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 conversations.  She admitted her dating skills which she thought long forgotten were back by date #3.


Lesson 4:  Pick the Right Dating Site.

When Tim, 53 from Philadelphia called me mid-February, 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 fifth date with Joanna, a 56-year-old realtor, and my fingers are crossed!


there are no bad dates. only good brunch stories

Lesson 5:  Engaging, Fresh Photos Produce Results.

Jill, a 46-year-old single woman from Chicago contacted me in late January after dating became a full-time, dreaded job, she thought.  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 2-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, and her dates increased, she met Brian, 44, and they’ve been dating for two months now.   The photos were fun and many men commented on that.


My goal is always to 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, which is what I love doing.


Love and Laughter.

andrea mcginty top dating coach


Andrea McGinty

Dating Coach 


Andrea McGinty founded the iconic It’s Just Lunch dating service in 1991 — before internet dating!  She sold it at its peak. She then founded when she realized, again, the help singles needed navigating online dating. In the 2020’s, she is more than ever convinced the best way to meet people is through online dating, using a professional coach/expert. Andrea thinks she has the best job in the world and specializes in singles in their thirties to seventies!



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