Online Dating Experiences

Online Dating

12 Good & Bad Online Dating Experiences

Amber Brooks

Written by: Amber Brooks

Amber Brooks

Amber Brooks is the Editor-in-Chief at When she was growing up, her family teased her for being "boy crazy," but she preferred to think of herself as a budding dating and relationship expert. As an English major at the University of Florida, Amber honed her communication skills to write clearly, knowledgeably, and passionately about a variety of subjects. Now with over 1,800 lifestyle articles to her name, Amber brings her tireless wit and relatable experiences to

See full bio »

Edited by: Lillian Castro

Lillian Castro

Discuss This! Discuss This!
Advertiser Disclosure

Online dating comes with no guarantees that you’ll have a good experience. You chat with a stranger, roll the dice, and hope your first date goes well. I’ve found my expectations overturned more than once by my online matches. Sometimes I’m excited for a date, and it goes really poorly. Other times, I’ve gone into the date thinking it was a waste of time and come away laughing at his jokes and excited to meet up again.

You’re bound to have a sprinkling of good and bad experiences while dating online. Sometimes it’s easy to feel like you’re facing those ups and downs alone, but thousands of singles are going through it, too. You can find consolation, inspiration, and a good laugh by hearing about some of the outlandish online dating exploits that go on, and we’ve got some humdingers for you.

Below, you can read through our top good and bad online dating experiences from real singles with the guts to put themselves out there. Some of these online daters came away with the love of their lives, and others, well, they were just happy to get away. Read on to get snapshot of the best of the best and the worst of the worst in the online dating scene. Enjoy!

Good | Bad

Good Online Dating Experiences (#1-5)

Any credible dating site is bound to have a long list of success stories and testimonials from singles and couples who say they’re happier because they joined the site. Whether those people found their confidence or their soul mate, such personal stories give singles everywhere renewed hope. It’s happened once, so, it could happen again.

We’ve collected some of our favorite online dating stories from around the web and in real life to bolster the spirits of daters feeling discouraged by ghosting, dick pics, and bad dates. Don’t be so glum, chum, there’s light at the end of the tunnel!

1. Whitson Signed Up for a Dating Site & Fell in Love Right Away

This first story is of unbelievably good luck. Whitson signed up for OkCupid and found his future wife within his first week. She had just signed up, too. They hit it off and soon started seeing each other exclusively, retiring their online dating accounts after a few short weeks.

“A few days on OkCupid was all it took for me to find the woman I would marry.” — Whitson Gordon, an OkCupid user who met his fiancée online

After dating for three years, Whitson married his online dating sweetheart in the summer of 2015. He said he considers himself incredibly lucky.

2. Finding Long-Term Romance After Nearly Giving Up

In 2009, Peter considered shutting down his eharmony account and giving up on online dating entirely. Then he met Ashley. She answered his messages, and they knew there was something there. In November, they had their first conversation over the phone. Their first date took place on New Year’s Eve, and they shared their first kiss as they rang in the new year.

The Californians maintained a long-distance relationship for the next year until Peter moved to Los Angeles in 2011. Nearly three years after that first nervous phone call, Peter got down on one knee on a bluff overlooking the ocean. She said yes.

3. He Took Me On a Wild Ride

I don’t personally like the first-date coffee-shop routine. It’s dull and unimaginative. When a guy I’d met online suggested we go to Universal for our first date (we both were annual pass holders), I jumped at the idea. Yes. That is what I want. A theme park of conversation starters and tight security. I’m in.

Photo of the Rip Ride Rockit Rollercoaster at Universal Orlando

I knew I was hanging out with a keeper when my date and I picked the same song to listen to as we rode Rip Ride Rockit.

We ended up having a great time. I think we were there for over six hours, talking the whole time, and at the end of the date he swooped in for a kiss. While the dinner-and-movie dates blur together, the date who rode a rollercoaster with me is forever imprinted on my mind.

4. A Once-in-a-Lifetime Love Story Begun Online

Sona Howell was taking down her dating profile, removing photos and information, when the photo of a 20-something guy caught her eye. She clicked on it and saw he lived a mere 10 minutes away from her. She decided to be daring — what did she have to lose? — and invited him to play darts at a pub down the road.

“I heard the tiny ding of the notification on my phone when I realized he’d responded back, and positively, even enthusiastically,” Sona recalled in an interview with SheKnows. “It’s funny, still, when we look back on it and realize that we were both so nervous we almost didn’t go.”

On their first date, they realized they were meant for one another. They got married on March 14, 2015 (aka Pi Day) and love to tell people that it was love at first click.

5. She Wanted to Cancel, But He Stuck It Out

One of my high school friends has been with her boyfriend for over three years now. They’re inseparable, and one of the cutest nerdy couples I know. For Halloween, they enjoy dressing up like sitcom couples. They’ve gone as Jim/Pam and Sheldon/Amy so far. They’ve got the same wacky sense of humor and often try to make each other laugh while eating or drinking.

Photo of Jim and Pam from The Office

As Jim and Pam taught us, having a good sense of humor makes for a solid relationship.

When they first met, however, it wasn’t all laughter and romance. In fact, she tried her best to avoid meeting him in person. She made him wait through a month of messaging, rescheduled their date three times, and went into it with an openly cynical attitude. And they ended up having a fantastic time.

He treated her to coffee, which turned into getting ice cream, which led to grabbing dinner. She now can’t believe she was so resistant to meeting the Ricky to her Lucy.

“I knew if she’d just give me a chance, we’d be fine,” he told me later. “And, anyway, she was totally worth the wait.”

Bad Online Dating Experiences (#6-12)

My friends and I often get together to vent our frustrations with online dating. I’ve heard so many stories about catfishing dates, no-shows, crazies, dull duds, blabbermouths, and a guy who pretty much only said “Right on” the entire night.

It’s kind of fun to hear these stories and try to top their bad dates with one of my own. As in, “You think dating a fanatic Green Party vegan is bad? I was stuck talking politics with a redneck Trump voter!” To give you a laugh and let you know we all end up on bad dates sometimes, we’ve put together a list of bad dating experiences from singles who probably regret every decision that led them to be on this list.

6. How I Learned the Hard Way Not to Answer Every Message

I’ll go first. My first day on a dating site, I was pretty overwhelmed by all the random guys checking me out and sending me messages. Maybe some girls would feel flattered by the attention, but I felt uncomfortable. I wasn’t interested in 90% of the guys who came my way, but I thought it’d be rude to ignore their messages.

So, I started giving would-be suitors polite and brief answers before explaining that I wouldn’t be striding off into the sunset with them.

“We don’t even know you. We’re not trying to be rude — we are just trying to be efficient and to protect ourselves from immature, unwarranted insults.”Single Girl Blogging

Mostly, it went over well. Then one guy took exception to my rejection. He asked why, and I pointed out that we had nothing in common. He argued, flattered, and begged in a barrage of messages that barely paused for my responses.

Finally, I guess I wore him down, because he asked if we could just be friends. Naive single girl that I was, I said sure. Can’t have too many friends, right? Then he asked, “with benefits?” And I blocked him.

7. What Do You Mean “Cam Sex”?

Sometimes people make some weird propositions on dating websites. It’s an anonymous forum where some singles feel no shame about soliciting toe-sucking, anal, and other kinky behavior. One single woman was on OkCupid when her online crush suggested cam sex. She was open to the idea and asked what that would entail.

He replied, “Well, I figured we’d just lie down and like, thrust at the camera.” Uh. No. On most days, online dating is good flirtatious fun, but on some days it makes you feel like taking a week-long shower.

8. Apparently the Pharma Bro Had a Tinder Account

Jacklyn Collier said she had “a pretty good time”

on her first date with Martin Shkreli, but she went out with someone who’s now in jail so we’re going to go ahead and put this in the bad column of online dating experiences.

Photo of Martin Shkreli, former hedge fund manager and convicted felon

Who on Tinder isn’t immediately swiping right on notorious Pharma Bro Martin Shkreli?

At first, Jacklyn didn’t believe her Tinder match was really the smirking pharma-bro accused of raising the price of medication 4,000% overnight. To prove his identity, Martin texted her a selfie as well as pictures of his driver’s license and credit card. Then he asked her on a date. She was curious, so she met him at an upscale Japanese restaurant in TriBeCa.

She found Martin to be a fairly standard, somewhat-nervous date until the end of the night when he ordered an extravagant $120 tea. She refused his offer to buy her a cup as well. When he finished, she asked how he liked it, and he told her he didn’t really like tea.

“I thought of all the good I could do with that money — donating it to charity, buying a new winter coat, buying myself 20 Venti iced soy vanilla chai lattes,” she wrote. “He might as well have eaten a $100 bill in front of me.”

9. Sitting Across From a Homophobe

One bisexual woman had a bad experience on Tinder when she met a vegan named Alex for drinks. He brought up her sexuality, and she expected him to make a joke about a threesome, but what he actually said was much worse.

“To be honest, I don’t believe in gay marriage,” he said, unprompted. “I’m not homophobic — it’s just, if two men can get married, what’s to stop me from marrying my brother? I’d love the tax benefits.”

Instead of explaining the nuances of incest laws and unpacking that bizarre homophobic word jumble, the Tinder single decided to leave Alex to finish his vodka alone.

10. Didn’t Get Away Clean

One single guy deeply regrets hooking up with someone

he’d just met on Plenty of Fish. It seemed like a straightforward 3 a.m. booty call. They got together, had drunken sex, and parted ways. He said he was out of there within five minutes, but he took a souvenir with him. He got herpes from his one-night stand. Yikes!

11. He Was Lying the Whole Time

I recently heard a strange story about a friend who tried online dating for the first time last year. She met a guy who seemed to say all the right things. They’d both recently graduated college, lived only a few minutes apart, and wanted to be lawyers. Things between them soon became serious. Over the next few months, she enrolled in law school while he took a gap year to study for the LSAT and save up his money. She helped him study, looked for scholarships, and encouraged him to apply early for her law school.

Photo of a commencement ceremony at Winona State University

My friend’s boyfriend told her he opted not to attend his commencement ceremony, so he didn’t have any pictures of himself in a cap and gown.

They’d been dating for over a year when she saw a text on his phone about chem homework, and the truth came out. He hadn’t graduated from college. He’d flunked out and was frantically taking community college courses while lying to his family, friends, and girlfriend. He wasn’t taking the LSAT, and he didn’t want to be a lawyer. He was planning to apply to film schools and pretend he was going to a law school out of state.

Sometimes you think you’ve met a great guy, and it turns out he’s a pathological liar. They broke up, and now she does a thorough background check on her dates.

12. Then She Pulled Out a Knife

Last of all, you know your love life has hit an all-time low when your date pulls a knife on you. Reddit user Hugit0 thought he’d made a good match on Plenty of Fish, but when he picked her up for their first date, she pulled a switchblade out of her purse. She pointed it at her date and told him not to try any funny business.

“I swear I thought I was getting robbed,” he recalled. She didn’t rob him, but she did seriously freak him out. Maybe her intention was to keep him from attacking her. All pulling out a knife did, however, was ensure that he’d never want to see her again. This cringe-worthy story is one of many reasons why driving together to a first date is a horribly bad idea.

Now Get Out There & Make Your Own Online Dating Experience

We’ve had some laughs relating these stories of the good, the bad, and the ugly on dating sites, but talking about online dating isn’t going to help you succeed at online dating. You’ve got to get out there and have your own experiences fending off bad dates and falling in like with good dates. Who knows? We could be featuring your unbelievably cute love story on one of these lists someday.

Sure, online dating is a bit of a gamble, but it’s also a lot of fun wondering where you’ll go and what’ll happen next. Whether you end up sitting in awkward silence or instantly hitting it off, you’ll definitely come away with an interesting story to tell your friends. Good luck!

Advertiser Disclosure is a free online resource that offers valuable content and comparison services to users. To keep this resource 100% free, we receive compensation from many of the offers listed on the site. Along with key review factors, this compensation may impact how and where products appear across the site (including, for example, the order in which they appear). does not include the entire universe of available offers. Editorial opinions expressed on the site are strictly our own and are not provided, endorsed, or approved by advertisers.

Our Editorial Review Policy

Our site is committed to publishing independent, accurate content guided by strict editorial guidelines. Before articles and reviews are published on our site, they undergo a thorough review process performed by a team of independent editors and subject-matter experts to ensure the content’s accuracy, timeliness, and impartiality. Our editorial team is separate and independent of our site’s advertisers, and the opinions they express on our site are their own. To read more about our team members and their editorial backgrounds, please visit our site’s About page.