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 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. My son was planning to marry a girl who he had met locally, no dating site needed. When she told him she didn’t think they were meant to be together forever he was gutted. I was gutted for him. My husband was reassured; he didn’t think they had been right all along. If I’m honest I too had had a sneaking feeling it wasn’t quite right but didn’t want to prick his bubble.
    A few months after I spotted a dating website (a Christian one as my son and I are believers) and it just lit up in my face, it seemed just right for my son. I forwarded the connection to him. A friend told me it wasn’t my role to set my son up with dates and that I shouldn’t have interfered. Beam in guilt and overbearing mother syndrome. My son didn’t respond to my forwarded message so maybe I had overstepped the mark.
    He started dating a lovely girl, we don’t live in the same area any more, so when he and I met up for a chat together in a coffee shop, I asked him how he had met her. He said ‘You know that dating site you sent me . . .I went on there and saw her, I hadn’t even paid any fees. I got in touch straight away, met her, and came off the site!’
    She is brilliant, they are definitely the right match, and are getting married this year.
    Moral of the story: sometimes we can help others find their right match, and parents in a good relationship with their kids may be part of that journey.

    In the final analyses dating sites are about a one to one special relationship, but when you open up your search aspirations to friends and family it may be safer, wiser and more likely to get you the right match at the right time. Sometimes, blinkered by unrealistic hopes, we can’t see what other people can.

    Since my husband wanted to separate in March 2018 I’ve been going through the grief and loneliness that brings. Just recently I started looking at dating websites, but friends are saying I’m not ready. It is tempting to fill the gap . . .and relatively easy as the dating sites are so effective, but I don’t want to cause another human being to be discarded and hurt the way I have been. It isn’t just about what I want. I’m learning to be cautious and patient, to think of others as more important than myself, then the right time and match will come.
    Guard your heart, says scripture, it is the well spring of life. When we open our hearts too soon and too often they get battered, and batter others.
    The desire for sex can be so strong! It drove me nuts in the first few months, it felt like electrical wires had been brutally cut and were sparking pinions of pain that wanted to fly to the next available man! Not a good reason for searching dating sites (and I didn’t but I struggled around Lycra clad sporty men on push bikes) But overtime the wounds healed, with Gods help, . . .self control is a fruit of the Holy Spirit . . .and now the desire is folded away, like a rose bud within. The right time for that to flower again may come, but I see it as the most precious part of my identity, the part that makes two become one. For me, a life of peace, patience and purity far outstrips the uncontrolled passion that robs your brain cells of any sensibility as fast as you can drop your underwear.
    Moral of that story: would you trust your expensive car, or iPad complete with passwords, with any old person you just met? Our worth as humans is above rubies, maybe we should be sure the person we give that to understands how precious we are, and how vulnerable to theft, damage and pain.

  2. This was a good read. Nice to know that I’m not alone as I have experienced so many bad dates. I keep thinking I will just delete and give up, only to hang in there thinking it just takes one good guy.

    • Thank you, Beth. That is a great attitude. A significant number of people give up after a bad experience. Our book aims to help avoid them so that more people can benefit from online dating.

      We would like to interview you for the book so please get in touch at at

      I hope the next date is Mr Right!
      Lindsay A Gordon

      • Beth, online dating can be such an ordeal but it can also be a fabulous delight. Hang in there ..better to be in the pond than out. Your perfect catch could be be close by or far away. The key is to believe in new experiences and never give up 🙂
        LauraJ Wareing

    • Beth, online dating can be such an ordeal but also an incredible delight. But it is so much better to be in the pond than out.
      Your soulmate might be near or far, but you’ve got to be in the water to find him.
      The key is to savour the experiences and believe.
      LauraJ Wareing

  3. 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.

  4. 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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