Skip to Content

Run ins

Oh Look, My Parents And Kids Just Happen To Be Here!

I am in my mid 30's, educated, independent, have never been married with no children. I went out on a limb and quit looking for someone of my age with the same characteristics as far as marriage and children are concerned. I met a female and had a wonderful message correspondence for a few days prior to agreeing to meet for a Saturday afternoon lunch. We covered most all of the typical stuff via email, I knew she was divorced with two children (10 & 13), worked in a professional business setting (I admit I never dug too deep via email to find out exactly in respect to privacy) and was living in her parents second home, but not with her parents. Being the economic times we are in, I could understand the financial trouble of a single parent and the living arrangement, I took it as a sign as coming from a close family that helped out when they could.

Your alias: 
E.B. in Michigan
You: 
Male
Your Date: 
Female
Where you met: 
Plenty Of Fish
Average: 4.1 (7 votes)

My Creepy Grade Nine Teacher

I had just started first year of University and while my school was in the town I lived in I had kind of lost touch with my old friends and was feeling lonely.

I had no money for internet dating so I placed an ad on Craigslist. Sure enough my very cute and wholesome ad brought all kinds of creeps out of the woodwork.

One guy, who was quite a bit older, seemed kind of nice so I emailed him back. After three or four emails things started to get kind of sexual. This wasn't normal for me but I figured I'd play along a little. After several more of these messages he sent me an solicited dirty photo of himself.

It was totally gross, and he had a tiny penis. As I looked closer at his face I suddenly realized he was my grade 9 history teacher, yuck! I emailed it to my old high-school anonymously.

I never saw anything in the news so I guess he was able to do some quick talking ;-)

Your alias: 
anonymous
You: 
Female
Your Date: 
Male
Where you met: 
Craigslist
Average: 2.8 (8 votes)

Ran Into My Boss While On A Date With Total Slut

I work for Christian run charitable organization. Obviously my boss is very religious, but to me it's just a job.

I had been hard up in the dating department for several months and needed to get laid in the worst way. I had been seeing ads for Adult Friend Finder around the web and decided to sign up.

The woman on there are basically just looking for casual sex, which suited me perfectly. After several days of searching I agreed to meet a girl fun lunch near my office... that was my first mistake.

She asked me what was appropriate to wear at the restaurant. I told her to wear the sexiest outfit she had, that was mistake number two.

Picking my boss's favorite restaurant was mistake number three!

This slutty chick showed up with her long bleached blond hair, nose ring, collagen injected lips, big fake tits, and was wearing a mini skirt and tube top. A great look for what I was planning... but not exactly material for bringing home to mom.

Your alias: 
frank895
You: 
Male
Your Date: 
Female
Where you met: 
Adultfriendfinder
Average: 2.3 (9 votes)

Set Up With My Hot Cousin

I've had the worst luck with dating for about the past year, since I got divorced. I did the online dating thing on a bunch of different sites and just couldn't seem to get a woman to go on a second date... no there is nothing wrong with me. I think I have just lost my confidence.

A buddy of mine from the office had been dating this hot girl that recently moved to town. I went out for dinner with them one night and she offered to set me up with a new friend of hers. I was skeptical, but hot chicks usually have hot friends so I figured I'd give it a shot.

We decided to meet at TGIFs. I hadn't spoken with her before hand and just had a description... 5'6", beautiful face, tanned, long blonde hair, thin with huge boobs, and hilarious. Once I got a look at her I agreed with the description 100%. She was incredibly hot... unfortunately, she was also my cousin!

Your alias: 
anonymous
You: 
Male
Your Date: 
Female
Where you met: 
Fix Up
Average: 4.6 (15 votes)

He Drives A Red Camero

I was telling a new friend of mine about my boyfriend. I told her his name and where he is from. She interrupted me and says "Yeah he drives a red Camero, and works at Microsoft?! I dated him two years ago!" I had been going out with him exclusively for four years.

Your alias: 
anonymous
You: 
Female
Your Date: 
Female
Where you met: 
Library
Average: 4.1 (11 votes)

Double Dating With Mom

My mom invited me to meet her boyfriend whom she had been seeing for a couple of months. She wanted to do it up right so we planned to get together along with his son at Milestones. Imagine my surprise when she led me to a table and my boyfriend and his father stood up, shocked, to greet me. Rather than being horrified, she is now planning double dates every week.

Your alias: 
Mandy
You: 
Female
Your Date: 
Male
Where you met: 
Milestones
Average: 3.3 (8 votes)
Syndicate content