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5 Online Dating Lessons Learned

dating lessons

As a dating coach for the past 25+ years, I counsel my clients at 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, 37, 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, 42, an attorney from Brooklyn.  It was instant chemistry---they both love chess, volunteer at an animal shelter and laughed the entire 90 minutes.  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, 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.


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 4 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, 53 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 28 years (and over 65% 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!


Lesson 5:  Engaging, Fresh Photos Produce Results.

Jill, a 46-year-old single woman from Chicago contacted me in February 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 3-hour shoot, we had photos of her horse back 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, 44, 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! 


Andrea McGinty has been featured on Oprah several times as America's Premier Dating expert. She founded the iconic It’s Just Lunch dating service in 1991 — before internet dating!  After selling it with over 100 locations globally, she then founded realizing, 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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