Online Dating Horror Stories

When you’re single, you definitely know how to mingle. Going on dates is a fun thing – we get to meet other singles who also love to socialize. More than ever, in our current time, people are meeting online or through phone apps set up to help you meet and date someone from across the web. In fact, the online dating site eHarmony reports that there are 40 million Americans using online dating websites, where 27% are young adults, which is up 10% from 2013.

Online dating can be a fun experience and is a nice way to meet people. Now that online dating is becoming more common, people don’t have that stigma. However, just like any dating situation, there are a handful of horror stories from meeting people online. 

Here are the top 5 online dating horror stories as pulled from

*All submissions below belong to Secure Single is referencing and crediting all content submissions 1-5 below to 

  1. Submitted by kiah4c

I went for a drink with a guy I had been chatting with online. He seemed pretty normal (good job, intelligent, funny). His first question on sitting down with our drinks was whether I was up for anal. I bypassed and watched him drink his body weight in shots before he started crying about his ex-girlfriend and then threw up down my shoulder when I was trying to walk him home. This was around 18 months ago, and he still messages me from time to time with a “hey,” or my favorite, “I miss you.”

  1. Submitted by KattieQ

I was once talking to this guy online and after a few hours of nice, PG conversation, he did a complete 180. He asked where I worked because I looked familiar… He said I looked like a girl from an amateur porn video. I knew that was not possible. He then asked if he could jerk off while we continued our normal conversation. After he tricked me into continuing the conversion for a few more minutes, I told him good-bye. Then he barraged me with dozens of lengthy messages asking to help him orgasm by telling him what he was doing was normal. Apparently, he had issues with disapproval and couldn’t finish without me telling him the simple letters “OK.” I never responded.

  1. Submitted by katet4dbf41478

I had been chatting with a guy on Yahoo Singles for a while, and we got along fairly well. When he asked me out to dinner I figured, sure, why not? It was singularly the most awkward and uncomfortable evening I have ever spent on a date. We spent our time attempting to make disjointed conversation… At the end of the evening we just simply said good night, and I figured that was the end of it. Approximately six months later, I received a message from his Yahoo account that roughly said the following: “Hi! This is X’s brother. This is going to sound really odd, but X is in prison for a few months (a big misunderstanding!) and I know he’d really like to hear from you. His address is through the ABC Correctional facility. Please write him!

  1. Submitted by estees2

I was speaking to this guy on Tinder, and after only a few minutes he asked me if I would marry him for $10,000. No joke. Apparently, he was a foreigner and wanted to become an American citizen. He couldn’t comprehend why I declined. He said, “Other people would do it for half the money!” I was like, “Not me, hun!”

  1. Submitted by Kris Woods (Facebook)

eHarmony matched me with my ex-husband…after we were divorced.

The online dating world is still early in development and should be taken with caution. If you are curious and want to learn more about people who meet their online date in person, check out episodes of Catfish.

If you do jump online and peruse the dating marketplace, just be safe and let your friends know what you’re up to. You could either have the next horror story from a first date, or you may meet the love of your life. According to, 5% of committed married couples met online. Be safe either way and have fun with it. If you’ve got a profile online for a dating website, be authentic and ask friends to help you polish your profile to present you in the best and most original way. Have morals when you are online and know when someone on the other side crosses the line. Don’t be afraid to stop a conversation.

If you do have a hilarious or seriously horror-ish dating story, we would love to hear about it. Submit your comments below. Happy dating Secure Singles!

For more stats on online dating, check out StatisticBrain.

Views expressed in this article are the author’s opinions and do not necessarily reflect the views of Secure Single. It is intended for informational and educational purposes only. It is not investment or financial advice. James Bollen is the author of Thriving Solo: How to Flourish and Live Your Perfect Life (Without A Soulmate). Now available in paperback and for the Kindle on Amazon. Subscribe to Secure Single’s Substack for free!
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Danielle has chosen to be single in her walk of life. She experienced dating in her late teens and early twenties, and had always felt each relationship was unfulfilling. To find more meaning in her life, she broke off to go down a path of self-discovery.
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