What's the quirkiest date you've ever been on?

Question

OlderAndWiser · Accepted Answer

Long answer but you need the complete story to appreciate it.

When I was 23, I lived in an apartment complex. I was on a second floor and there was only one other apartment accessible via that stairwell. It was occupied by a 46 year old divorced woman (physically a 5/10) and her 17 year old drop-dead gorgeous cheerleader daughter (a 9.5/10.)

I was leaving town for a week and needed someone to feed the fish in my aquarium, so I asked my neighbor (46) to feed my fish and water my house plants. When I returned, I thanked her (and retrieved my apartment key,) and offered to take her out to dinner to thank her for the help. To my great surprise, she said she would love to do that, so I asked her where she would like to go, she mentioned a Japanese steak house on the Courtney Campbell Causeway, and I made a reservation for a Saturday night.

I drove us there and we had dinner. The restaurant was somewhat dated and dilapidated but looked clean and the food was actually very good. The conversation flowed more easily than I anticipated; maybe because she had drank a few alcoholic drinks. (At that time, my mother was 47 years old and I couldn't forget that.) After dinner, she said she had really enjoyed herself and wasn't ready for the evening to end, so I politely asked her if there was something else she would like to do.

She mentioned a piano bar lounge that was nearby, so we went to the piano bar and ordered a drink. Almost all of the people in the lounge were "old" people (middle aged) and the pianist was playing old people's music. She asked me to dance with her and the pianist was playing slow music, so we started doing the "hug and wobble." She placed her left foot between my two feet so that her crotch was rubbing against my thigh and my crotch was rubbing against her thigh. In retrospect, I think this was all carefully orchestrated. Before long, she was softly whimpering.

In those days, I had a few casual sexual encounters and she was certainly getting me worked up. After a few more slow dances, she asked me to take her home. I walked her up the stairs and she invited me in to her apartment for a "nightcap." She informed me that her daughter was spending the weekend with her ex.

She actually did make me a drink and we sat on her sofa and talked briefly but it soon turned into an animal mating frenzy. We made our way to her bedroom and she proved to be a rather inhibited, pure vanilla girl, but apparently she hadn't had sex in a few years and wanted to make up for lost time. Every time we finished and I rolled over in the bed, she pulled me back on top for another round. After about three hours, she finally fell asleep and I also drifted off, feeling drained and satisfied in a weird way.

We had a few more dated but she then broke up with me because she accused me of just wanting her for sex! Really.

I've never had another date like that first date!

HawkPerception · Accepted Answer

With my second ex, we met up at a Starbucks and had a typical coffee date. We enjoyed each other's company and went for a nature walk. I decided to ask if she wanted to go off trail, and she was in, but it was a little muddy. She had boots, but I had some shallow shoes I didn't want to ruin, so I went barefoot and carried my shoes. We went pretty deep into the forest, talking and laughing all the way, and then I asked if I could kiss her. She said yes and then as we were kissing, a deer came strolling by and stopped and looked at us. It didn't look as if it was poised and ready to run or anything. It just looked like it wanted to witness us. It was a pretty magical moment and we remembered it forever. I had ants crawling up my leg, which made her laugh pretty hard, so we ended up moving and getting out of there. And in the end, we had no clue where we were, but we had to hop some fence that I helped her with. And finally ended up finding the road.

Definitely a memorable date 😂

Zoi1986 · Accepted Answer

A lady I went on date with wanted to do the lady and Tramp.

exitseven · Answer

I met up with a bunch of friends at a bar one night. There was a girl there that was the friend of a friend. We seemed to hit is off. We were talking most of the night. She was a couple of years older than me and just graduated from college. My friends knew her because she was their RA in the dorm where they lived. It was getting late and I offered to drive her home. When i got to her house I was just about to ask her if she wanted to go out sometime but instead she invited me to a party she and her roommates were having the next Friday.

I looked forward to it all week. So on Friday I drive over to her house. I expected to hang out with her and get to know her better. Instead she spent the evening on the phone talking to some guy and crying.

I got really drunk and left without saying goodbye. I never saw her again.

RyanR03 · Answer

Um so… a girl I knew in high school ended up at same college I was at. Well she saw me out running a few times. I think she thought it would be neat to run 4 miles with me before we went out. She was like, “let’s do a jog. You like to run , yeah? And then we can go change and go out after”

im like “um ok” (… but sort of on MY workout regimented workout schedule and not as a predate-date). 😂

🤷‍♂️.

and then one girl I knew said she read this book about these 2 teens that would hang out in a little league dugout and look at the night. So she wanted to do that with her. After a quick dinner. And so we went way out north and sort semi broke into the Junior college field and went into their concrete dugout. And we made out of course but I was not overly comfortable

obviously these are 2 dates where they picked the date. Normally I did but maybe that’s why they were at least odd 😂

ArrowheadSW · Answer

I met a lady with somewhat common interests on a dating site. We met up at a Starbucks. She wouldn't have coffee with me because she said that she didn't consume caffeine. She wouldn't have any of their other drinks because of "added sugar". Anyway, as we were talking, she asked me for my date of birth. Then she also asked what time of day I was born. She got a confused look on her face and briefly looked up to the ceiling in a state of thought, then said, "I'll have to draw you up an astrology chart"... LOL I guess she took astrology seriously. On the way back to our cars, she showed me her car and it had some colored paper taped to the inside of some of the windows. She said that it helps her find her car in a parking lot. A few months later I was at a red light at an intersection, and a car with colored poster paper in the windows made a turn in front of me. Of course it was her... LOL

OfMiceandMen · Answer

Went out on a double date with my buddy and we ended up trading gfs once we got to know one another. However, he lasted 8 months with his girl and I lasted 5 years.

SixFootSexy · Answer

I dated a librarian once. She was a lovely girl, extremely quirky and shy, she accidentally locked her keys in her car when she came to pick me up (LDR) but she was also asexual which was a dealbreaker for me.

Another instance, I went on a date with a woman and her recently divorced, ex-husband showed up. He didn't confront me, just stared her down as he left. It was awkward.

worldscolide · Answer

That's easy. We met at a restaurant, and before we ordered anything, she asked me if I was okay with buying her kids meals she could take home to them. She had originally told me she had no kids.. I got up and left. Less than 10 minutes.

elaphe · Answer

I was at a park with my girlfriend in college in my car. A police officer came up and asked us what was going on. We told him that we were just sitting there. He didn't buy it and told us to move along.

slatyb · Answer

A woman brought her teenage daughter to a lunch date.

RebelinSteel · Answer

A hot air balloon, we were supposed to be going for a trip on a narrow boat but that fell through and a friend offered up a ballon flight. The hardest part was waiting for a decent day to do it.

BCRanger10 · Answer

Probably my first date with my wife. It was basically the "building a castle in a swamp" scene from Monty Python and the Holy Grail.

Stef12 · Answer

I think I only had about 4 dates. Just went for a meal.

MicahRaine · Answer

I haven't been on many quirky dates, unless you count hiking or thrift shopping.

TedBr · Answer

During university when I was set up with a girl by my buddy. It went very odd but we both had fun agreeing that we are not meant for each other

Sambobelfast5163 · Answer

20 minutes and she wanted me to take her home.

DrPepper12 · Answer

Anniversary dinner ruined by trump getting shot at. 🤬

Iron_Man · Answer

7 minute blind date, some weirdo girl

legalboxers · Answer

nothing as of yet

CubaPirate · Answer

Amsterdam by train from the UK 🇬🇧

What's the quirkiest date you've ever been on?

Most Helpful Opinions

What Girls & Guys Said

What’s the most fun date you’ve ever been on?

What's the quirkiest date you've ever been on?

Most Helpful Opinions

What Girls & Guys Said

What’s the most fun date you’ve ever been on?

We're glad to see you liked this post.