Couples Share Their Best and Worst Online Dating Stories

Couples Share Their Best and Worst Online Dating Stories

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So you’ve signed up. You’ve checked out our safety tips and now you want to know how to dive into online dating and get the most out of it.

Voila! Learn from our “secret stories” to successfully ride the dating game wave.

For our upcoming online dating book, His Advice for Her – Her Advice for Him, we interviewed hundreds of users of online dating over a 10-year period. Some of their illuminating, entertaining and unfortunate stories, as well as our own, are below to share with INSPIRELLE readers tempted by e-dating. No real names appear!

Lindsay A. Gordon and Laura-Jane Wareing have penned a 3-part series for INSPIRELLE that gives you the tips to survive and then thrive within the world of online dating. The two writers met e-dating years ago; sparks did not fly but the creative juices flowed and produced a successful writing collaboration.

Online dating

Don’t listen to your friends

SHE SAID – If I’d listened to some of my friends at the start of my relationship with my husband we wouldn’t be together now. It’s a learning curve, and yes, you do know best.

HE SAID – John was very excited about a new find via online dating and informed his best friend, Rosie. Rosie told John all the things that were wrong with his new date. Why? Rosie was sabotaging his new relationship because she was in love with John (fortunately, he didn’t find any bunnies boiling on the stove)!

Never trust a picture

SHE SAID – My husband encountered this on a fair number of dates pre-me. The stories are now told with some hilarity for the excuses given. Like the lady whose photo was taken a few years before. He was so excited – it was his first online date. Imagine his surprise as the attractive woman in the picture bore no resemblance to the woman walking through the café doors.

HE SAID – I had a date in London and the lady who showed up looked significantly older than her profile photo.

I asked politely, “Hmmm, you don’t seem to resemble your photo all that much?”

She replied casually, “Oh yes, that’s right, that photo was taken 10 years ago – that’s alright isn’t it?”

I ended with, “No, not really!”

Online dater Danielle in Paris. © Cindy Lin

Always link up on the phone, Facetime or Skype first

SHE SAID – I spoke to my now husband loads before we actually met. He was traveling madly, I was busy with various deadlines, and it was a lovely way to connect and test the vibe. I still remember the butterflies and light up smile I exuded when I spoke to him.

HE SAID – Colin had found a beautiful woman online in Australia. She was super sexy. She was the right age. She was educated. She liked everything he liked. They exchanged emails and it was perfect. Colin could not believe this woman was not taken already. However, they never had the courage to talk on the phone. When they finally met, it turned out she could not hold a conversation and was crazily nervous the whole time.

Out to dinner is not a first date thing!

SHE SAID – I met a guy for supper, one of my first dates, and found myself looking for excuses to leave. The date simply wasn’t working for me and I wanted to flee.

HE SAID – Everyone has a single friend they think would be perfect for you. James went to a friend’s for dinner and had to suffer a woman who resembled a horse. James decided to sabotage the blind date by creating a rebellious drug lord alter-ego. The unfortunate side-effect was that James had annoyed his friend who had set up the date. The final audacity, at the end of the eve, was for James to ask his blind date if she wanted to share a taxi back to his place.

© Jack Finnigan/Unsplash

Always have a plan B

SHE SAID – My go to was “I’ve got a really big deadline to finish, and don’t want to be in bed too late tonight.”

HE SAID – I was out on a date with Isabelle in France and she had forgotten to text her “safety friend.” So, when our date was going great and the clock struck 10, her safety friend showed up to escort her away! The three of us ended up having a good night, regardless.

Are you ready for online dating?

SHE SAID – I’d just come out of a five-year relationship and rushed into online dating for the company. After a pretty lousy experience on an e-dating website, I had to pull the plug, turn the machine off and regroup. Asking myself a myriad of questions –most importantly: was I ready for online dating?

– Rick had spent the night with a date he found on Tinder, in the US, and awoke to find her crying buckets on his chest chatting about her ex. She certainly wasn’t ready for online dating.

Josiah, online dater. © Cindy Lim

Don’t overthink the response your profile gets, just widen its net. 

Through six degrees of separation you may have access to 1,000 people and from them, one may be your perfect match who likely will already be taken. With e-dating, we have the opposite problem. You can find 1,000 perfect matches from a casted net of 100,000 Mr. Wrongs and Ms. Terribles.

SHE SAID – I searched and scoured the dating site mysinglefriend after many rejections on Guardian Soulmates. I was looking for someone exciting. I found him, approached him with a message, and bingo! Here I sit married with two kids.

– A gentleman in Paris used OK Cupid to find a romantic partner in his later years. He is quite the dynamo and has the sex drive of a teen. He would make a great date but sadly was turned off online dating. Why? A woman had needlessly messaged him to say, “You’re too old.”

© Cindy Lin

Missed connections – watch your spam folder!

SHE SAID – I activated my account on mysinglefriend and my husband was my fourth date. My first three dates were lovely but there was no special connection. I had stopped paying for the site and was about to give up. My last act was to leave a message for my future husband. He had to pay extra to respond as his account had just expired. His email to me ended up in my spam folder and was retrieved just before it was officially trashed.

HE SAID – After some good dates an e-couple, Randy & Jules, came unstuck. They were at the stage of phoning each other occasionally. Randy made some effort to engage Jules again but the calls were not going through.Jules assumed Randy had lost interest but that was not the case! Meanwhile, several other dates were waiting for Randy online and he forgot about Jules.

Have a second mobile number as backup

SHE SAID – A girlfriend went on a date with a man she found on Tinder. They exchanged their info. Then he began phoning four times a day. She politely cut communications. With the information she already gave, he researched her home address to continue the conversation. He showed up at her house a few times, which freaked her out, but fortunately, he backed off after further rejection.

HE SAID – George was out on a date and Francine, his e-date, wanted to know a few things:
“Have you used the dating site much?”
“How many dates have you had?”
“Did you sleep with any of them?”
“Are you still seeing any of them?”
“How many women are you messaging right now?”
Francine had more questions, probably, but it didn’t matter since George had already left, via a very, very long trip to the toilet.

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Don’t dress to impress

SHE SAID – I remember a friend going on a date, one of her first, slightly overcooked. You know… too perfected and smart. It ended with her feeling so awkward that she spilled her coffee onto his lap – and yep, the date ended there!

HE SAID – Rick from California had met a woman using social media on his iPhone. She showed up to his date very well dressed. She was dressing to impress, ignoring her habit of dressing in chill clothes. She was incredibly uncomfortable the whole night. Luckily, near the end of an awkward date, they got to talking about this. Rick liked everything about her except the way she dressed, “it doesn’t suit you!”

Make a list of who you’ve met

SHE SAID – A girlfriend was excitedly telling me about this guy she’d found online. She had this sort of familiar feeling with him, which she said was serendipitous. “Could be the one,” she enthused. It turns out she did know him — they’d met on another dating website a few months before!

HE SAID – Jason had the online dating game sorted. He was using three different dating sites and keeping multiple women on the go. He could always have a date any night he wanted. But without a filing system, he would sometimes mix up women’s names or details about what they talked about. As far as he was concerned, this was the price of doing business. He would lose a few fish but there were more fish in the sea (Plenty of Fish was one of the services he used). He did tell me that he slowed down after a while because he started feeling like it was a full-time job!

For more tips, watch out for our up-coming book “His Advice For Her; Her Advice For Him”

Ready for some e-dating? Check out our roundup of most popular online dating websites.

Lindsay Gordon & Laura Jane Wareing
Lindsay A Gordon (@AuthorLAG) is an Australian writer living in Paris since the Charlie Hebdo attack. A strong supporter of the arts, he is Producer for the Paris poetry series, “Angora Poets” and Art Director for the global event “100,000 Poets for Change”. Current projects: writer for INSPIRELLE; co-writing a script for a French producer; a book called, "Outback in Australia and Paris", editing a new book from Jude Cowan Montague (UK); writing “The View from Paris” series which is published in the USA; and co-writing a book on e-dating with LJ Wareing. .............................................................................................................. Laura-Jane Wareing (LJ) is an English mum of two young children living in the leafy suburbs of West London. With a background in criminal law, LJ used her skills to help the needy and started her career as a healthcare consultant working in communications, crisis management and improving efficiencies in the NHS. Today, she sits on the board of governors for Chelsea and Westminster hospital and is also director of a business training and coaching company. Throughout she has had a love of writing and this has involved editing and a production of articles on various topics.


  1. Loves this article, thanks Lindsay and Laura Jane. It was a great format like banter going back and forth his and her story. This installment left me curious and waiting to read more.

  2. Thanks for reading. Laura-Jane and I will be monitoring these comments. We think it would be great if you could share a dating story that you may have heard. Good or bad! There may be a lesson to be learned for other readers . . . please do change the names, though!


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