The strange things people have done on dates.

The strange things people have done on dates and a guy got swallowed by a whale
Loving the Strange
Loving the Strange
The strange things people have done on dates.

Hey! Welcome to episode 18 of LOVING THE STRANGE where we talk about the strange, adorable things people do on dates!

Dates. What are those long lost things?

Thank you all so much for listening! This wouldn’t be fun if you weren’t here.

So here are a few stories.

I was set up by a coworker with his wife’s cousin. I worked in a deli at a grocery store. So our first meeting I was in a hair net and apron and no make up. I barely remembered what he looked like but we must have hit it off because the next day my coworker said the guy wanted to swap phone numbers. I wasn’t from this area so i was nervous when he invited me to a town I never heard of April fool’s for a bonfire. I took a chance and found my way there. When I arrived it was only me and him at his friends farm, no one had arrived yet. I was nervous. Once others arrived we went muddin in his truck amd danced under the stars in the light of the fire. His friend’s truck got stuck in the mud so my date went to help pull him out and his truck got stuck. They ended up dragging it out with a tractor but the truck wasnt in neutral so the tie rod end snapped. My date was upset so someone handed him a bottle of homemade wine. He got drunk but we still had a good time. At the end of the date he walked me to my car and said he was gonna go sleep on top of a silo. I was nervous he was gonna roll off and fall to his death…. So that was an awkward but memorable first date…. We have been together for a total of 10 yrs , 8.5 of those years we have been married. Still going strong

Amanda Courtney

Sad I missed this. My hubby and I connected online and our first date was in a nature park. I took us on a short cut off the trail to visit some horses that live on the backside of the park and we ended up lost in the woods for three hours

Autumn Gin

First one: I rode with a friend to her mom’s for the weekend (so I didn’t have a car) and they left to go somewhere on that Saturday. I had a friend (he was a guy) come pick me up to get Steak ‘n Shake. While we were eating my female friend came to get me to take me to her place. She comes in and goes “is this a date?” While I was saying “no” he was saying “yes”. Needless to say it was very awkward after that. 😂


Second one: I left an event early to meet up with this guy. He had an hour to travel to my two hours. When I got to the place we were supposed to meet I waited for like 15 mins before I found out he left. He told me he liked for people to be on time. For the record he never told me he was mad or that he was about to leave. He just left. side note: I ended up getting lost along the way so it took longer than two hours to get there Bonus story! It’s not a date but it is kinda strange and had to share (if it doesn’t fit though it’s okay ☺️) my friend at the time called me up one night. I answered and said “hello”. He proceeded to play Collied by Howie Day and sang the entire song to me. When it ended he just acted like nothing happened. To this day I have no idea what it was about but it’s the only time I’ve been serenaded 😂😂

Anonymous again. Also, um, the song was COLLIDE. 🙂

An all day date. Back when I was in high school I had a crush on this guy for a few months, and he FINALLY asked me out. Texted me the night before and was like “hey, I have rowing later in the day. Can we do a movie at like 10am?” I was totally fine with it, so that was our plan. He came, picked me up, and we saw the movie —- after the fact he looked at me and told me that he wanted to blow off the rest of his plans for the day and spend it with me. The second activity was bowling, which I’m atrocious at. I told him this, and he said that he was super good at bowling and maybe it would rub off on me, which I said maybe I’d be lucky this time. So every time we would take our turns, after his he would make a BIG show of “wiping off” his body and “rolling” all of his luck into a ball and throwing it to me (it was actually the best I’ve ever bowled). From there we went to dinner, and then went to every dock around the lake that we live on. On the final dock, we were skipping rocks and he kissed me — it was my first kiss and I was literally shaking excited and nervous. It wasn’t anything SUPER special, but I’ll always remember it.


It was my second date with this guy, and he said the exact same things that he said on the first date. Word for word. The same stories, the same “random thoughts,” the same questions… It freaked me out so much that at first I played along and answered in the exact same way, as though we were both following some weird script. Eventually I tried to break the mold and ask him new things, but he would just bring it back around to the same topics as last time. It was like I was in a computer program and there was a glitch. Still freaks me out to think of it.

Reddit User IHaveTheMustacheNow – THE GLITCHING MATRIX

I had just moved to London, and met this guy on a dating website, he was generally not my type. Still, I was fresh out of a long term damaging relationship and trying to meet new people yada, yada.

Fast forward to the date, and he takes a call from a girl and he says to her – ‘oh i’m just in the pub with (male roommates name)’ I can hear her on the other end getting worked up about something and him telling her to calm down. Alarm bells already ringing.

He hangs up the phone and says ‘that was my fiance, but not a real one, just one i’m with for her visa’ At this point I’m already thinking ‘bloody hell’. He continued on with his excuse ‘She also lives with me’ (in his 2 bed apartment with this other roommate – cosy). ‘Oh yeah, I should probably tell you i’m getting married in three weeks’

At this exact point, I just said ‘well, I’m going home’ and start pulling on my coat.

His reply was even more classic, ‘do you want to help me buy groceries first?’

Reddit User Clarieinthesnow

We had been talking on the phone for about a month already. He tells me his car is booted – outside of his house. He had a long drawn out story about how he could not get the boot removed. His dad was staying with him and he thought would be able to use his dad’s car but now he can’t. So I go to get him to go somewhere to eat. He starts panicking saying, “oh great, now I’m in the car with you and I’m going to get accused of rape or something.” I asked him what the hell he was talking about. He just kept rocking in his seat anxiously, worried that he would be accused of rape. I drove to the nearest area with food and asked him where he wanted to go. He said he had no money and wanted to go home. So I took him home. Then he asked me if he could borrow $20. I don’t know why, but I gave it to him. After this, he called me repeatedly and I ignored his calls. He texted me asking why he was “not good enough for me to date.” I kept ignoring him.

Fast forward 3 years. He is on a dating site I am on. He messages me but does not remember who I am. He tells me that a year ago his long time girlfriend passed away – the one he had lived with for 10 years. So, he was not staying with his dad, and he was freaking out because he lived with his girlfriend when he met me, right outside of his house. I called him out on it and he tried to pretend I had the wrong guy. But he had the same name and worked at the same place, and looked like the same guy. Very bizarre.

Reddit User Elleseven

Cool dating ideas from (Direct quote)

1. Play in the snow, build a snow man, then drink cocoa

2. Go to a community play, a dress rehearsal, high school or college play

3. Do an inside or outside picnic 

4. Work out together

5. Go roller skating or ice-skating

6. Movie marathon with ice cream sundaes

7. Play hide and seek in a corn field (or the woods)

8. Go on a very long walk around your neighborhood at night

9. Go to a real- live movie store, pick out a movie together then pop homemade popcorn at home 

10. Go to estate sales together

11. Spa night together

From PSILOVEYOU – How not to be a dick on a date.


Show up.

TALK THE WHOLE TIME – just you. Only you. Monloguer.

The good morning text.

Have some swagger but not too much swagger

Don’t go somewhere creepy unless you know the other person is into creepy.

Thank you all so much for listening! The extra shout-outs go to our high level patrons who also read Carrie’s books in progress and get some art in the mail sometimes.

Autumn Gin

Claire De Brey

Jenn Duffield

Pam Leffler

Joan Stradling

Nancy Stone

Sam Spellacy

Toni Floback

Shay Altair

Rachael Azbill


Author: carriejonesbooks

I am the NYT and internationally-bestselling author of children's books, which include the NEED series, FLYING series, TIME STOPPERS series, DEAR BULLY and other books. I like hedgehogs and puppies and warm places. I have none of these things in my life.

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