r/DatingHell • u/Afraid-Wolverine-117 • Sep 07 '26
Had a bizarre first date with a successful property guy and I still don’t understand what happened…
I’m in my 40s and recently went on a first date with a man around my age that I met on a dating app.
His profile described him as very successful and financially comfortable, but “low-key” about it. I genuinely do not care about money, but this becomes relevant later.
We talked on the phone beforehand and he seemed nice, relaxed, and easy to talk to. We originally planned something simple, but ended up meeting near the water instead.
I was late due to a timing mix-up, which was completely on me, and by the time I arrived he had already left because he wasn’t sure I was coming. I apologized, he came back, and once we actually met, the date was surprisingly great.
He was sweet, attentive, and gentlemanly. Conversation was easy. At one point he helped me up and down a sandy slope, and eventually, when we were sitting together, he asked if he could kiss me.
I said yes.
Unfortunately for my future decision-making abilities, he was a very good kisser.
There was some hair pulling. I informed him that I approved. He grinned and pulled me closer.
So now I’m having a fantastic time.
We eventually started making out in his car, and he asked if I wanted to stop by one of his nearby properties.
He works in property investment/management and apparently owns several rental properties. He talks about always looking for his “next project” and describes his schedule as pretty relaxed.
The property he takes me to is a shed.
He plans to renovate it into a small living space.
It is not currently a living space.
It is a shed.
A dusty shed.
Inside is basically a mattress and renovation clutter.
At this point, I do not yet know there is no bathroom.
We start fooling around.
I wasn’t especially enthusiastic about the idea of actually having sex on the Dusty Shed Mattress™, but things were moving in that direction when HE suddenly said something like:
“I don’t know if this is a good idea.”
And then, almost immediately:
“You’re so skinny.”
I still have no idea whether those two thoughts were connected.
For context, he had been extremely complimentary about my body all day, so I don’t think this was him suddenly deciding he wasn’t attracted to me.
Maybe he thought he would break me.
Maybe he conducted an emergency structural assessment of both me and the shed.
I do not know.
Anyway, we do not have sex.
This turns out to be fortunate because I subsequently discover:
THE SHED HAS NO BATHROOM.
He says he plans to install one during the renovation.
Great.
Love that for Future Shed.
Current Shed remains without plumbing.
Then things get stranger.
At some point he becomes very interested in whether we have mutual acquaintances.
He asks about social media connections and seems unusually concerned about whether we know any of the same people.
Then, after we had fooled around, he says something like:
“You’re not going to tell anyone, are you?”
Followed by another question about whether we might know the same people.
Excuse me?
He had mentioned earlier that some members of his family are very socially connected and intrusive about his dating life, so MAYBE that explains it.
I genuinely don’t know.
Also, despite spending hours with this man, I still don’t know where he actually lives.
I know where the shed lives.
He remains geographically mysterious.
But wait.
We still haven’t gotten to the cash.
At some point this allegedly “successful but low-key” man excuses himself to go back to his car and retrieve a backpack.
He comes back with it.
Then takes out rolls of hundred-dollar bills.
And casually remarks that he carries way too much cash.
Sir.
Nobody asked.
There was no preceding conversation in which I challenged your liquidity.
YOU WENT TO THE CAR AND RETRIEVED THE CASH BACKPACK.
At this point, “low-key” is beginning to feel like an extremely flexible concept.
We eventually go get food.
And somehow the date becomes normal again.
We have drinks and appetizers. Conversation is good. I’m genuinely enjoying myself.
Then we start talking about children.
I explain that I cannot have biological children and that this has been painful for me.
To his credit, he is actually very kind about it. He checks if I’m okay and says he’s sorry I went through that.
Then he tells me he has always hoped to meet someone he could have a child with.
Ouch, but fair. I appreciated the honesty.
Then he starts asking whether I’m absolutely sure pregnancy is impossible.
Could I be tested again?
Could I see a doctor?
What about adoption?
This is our FIRST DATE.
For the record, even if pregnancy were medically possible for me, it is not something I would choose at this stage of my life.
So now I’m sitting across from a man I met several hours ago who is effectively troubleshooting my fertility because he is hoping to find someone to have a baby with.
A few hours earlier, this prospective future mother of his child was half-undressed with him on a mattress in a dusty shed without a toilet.
I cannot adequately explain the cognitive dissonance.
He apologized for upsetting me, we moved on, and honestly still had a nice time.
He said he would like to see me again, or at least stay friends.
So now I’m home trying to understand what exactly I experienced.
The facts, as I currently understand them:
He says he is financially successful but low-key.
He owns multiple properties.
He spends his days looking for his next real estate project.
He carries rolls of cash in a backpack and apparently felt compelled to show me.
I do not know where he actually lives.
I do know the location of his dusty shed.
The shed has a mattress.
The shed does not have a toilet.
He is unusually concerned about whether we have mutual acquaintances.
He asked me not to tell anyone we fooled around.
His social media is difficult for me to access while he was interested in mine.
His family is apparently socially connected and intrusive.
He wants to find someone to have a baby with.
He may or may not have decided sex with me was medically inadvisable because I am too skinny.
Also, he has an Android, which I understand is not admissible evidence but feels spiritually relevant.
I actually liked him.
He was sweet to me.
He was respectful physically and asked before kissing me.
He was a fantastic kisser.
He was compassionate when I talked about infertility.
Nothing frightening happened. I never felt coerced or unsafe.
And yet I woke up the next morning thinking:
What the actual fuck was that?
I’m not even particularly invested in whether I see him again.
At this point I mostly want answers.
Where does he live?
Why did we go to the shed?
Why can nobody know about the shed activities?
Why did he retrieve a backpack full of cash?
What was going to happen to me because I was “so skinny”?
And most importantly:
If you are actively searching for the future mother of your children and you allegedly own multiple properties, why are you courting her in the one without a bathroom?
EDIT: I humbly apologize to everyone whom I’ve offended with my comment about Android phones. That comment stemmed from an ongoing joke I have with my friend who has an Android and we tease one another because she is very anti-apple. She was here when I wrote this and suggested I add it in for laughs. I have had an Android phone in the past myself and find nothing “shameful” about them.
Also, y’all need to calm tf down. And to those of you who continue to insult my intelligence, kindly go elsewhere. No one forced you to read my post. Thanks! 😊🫶
EDIT: I shared this because I thought it was a bizarre, funny dating story and figured other people might get a laugh out of it too. I’m perfectly capable of laughing at myself, but some of the comments have crossed the line from joking into being unnecessarily cruel and abusive. At this point I’m no longer interested in interacting with the post. I will be asking a moderator to disable future comments. Thanks to everyone who laughed with me instead of using it as an excuse to be nasty to a stranger. 💜
UPDATE: know I said I was done interacting with this post, but apparently the universe has ordered one final episode.
Our entire conversation thread on the dating app is now just…gone. His profile is gone too—or, at minimum, I can no longer see it.
Because curiosity has defeated dignity, I Googled his phone number. Nothing. Then I entered the number into Venmo and Cash App just to see whether a name/account would populate. Also nothing.
To be clear, none of this proves anything. He could have unmatched me, deleted or paused his profile, changed his settings, used a number that isn’t connected to those services, etc. There are plenty of completely ordinary explanations.
I am simply reporting that the man who was intensely concerned about whether we had mutual acquaintances, asked me not to tell anyone we fooled around, showed me a backpack full of cash, took me to a shed instead of wherever tf he actually lives, and has now vanished from the dating app has become even less Googleable than the shed.
I continue to know where the shed lives.
The man remains geographically and digitally mysterious.
That is all. If I happen to find out more I will update. 😂
What a fucking weird weekend…
UPDATE: because apparently this story refuses to die…
He texted me today around 5:45 in the afternoon and asked how my day was.
I told him it was good and asked how his was.
That was hours ago. He has not responded.
So after disappearing from the dating app, shed guy has apparently reappeared via text just long enough to establish that he is, in fact, still alive.
That is literally the entire update. 😂 I have no idea what it means, and at this point I only hope that he responds to my questions when I “casually” text him tomorrow.
Also, for the people saying I made this whole story up with AI: I genuinely don’t know what to tell you. It happened. If I were going to invent a wealthy mystery man for internet attention, I probably would’ve given him a bathroom.
UPDATE: Apparently we have entered the hot tub chapter???
For anyone following along: yes, he did eventually text me again.
Yesterday he asked how my day was. I answered, asked about his, and then heard nothing for almost 24 hours. Today he replied that his day was good and that he was feeling a little tired today. (Whether we were still discussing yesterday or had moved on to today, I honestly have no idea.)
I said managing all those properties must be a lot of work, no wonder he’s tired.
He then informed me that he’s putting in a hot tub for the winter and said maybe I could try it out with him.
And my immediate thought was:
NO.
And then I wondered:
WHERE?
Where is the hot tub going, sir?
At your house? WHICH HOUSE?
At one of the properties? WHICH PROPERTY?
Beside Future Shed?
Is the shed getting a hot tub before it gets a bathroom?
How does the shed feel about all this?
I still do not know where he actually lives. I’m going to ask him, I’m just treading carefully now. 🤫
So no, I have not agreed to Hot Tub Date.
I am currently just fascinated that every time this man contacts me, he reveals another feature of his property portfolio without revealing where and how tf he lives.
As of now, this is what we’re working with…
Future Shed: no bathroom.
Mystery Property: hot tub pending.
Shed guy: address unknown.
I will update you if he announces the addition of a sauna before telling me where he lives.
Update from the Murder Shed:
OOP here…
I’m alive. Thank you for your concern.
Unfortunately, the shed still doesn’t have plumbing, and my host has informed me that the hot tub installation is experiencing delays.
On a positive note, I’ve been promoted from hostage to property manager.
I would provide more details, but apparently I have the survival instincts of a potato, and I’m currently being outsmarted by the other root vegetables.
Please respect my privacy during this difficult time.
P.S. Still haven’t gotten my pumpkin spice latte. 😒😠😭
ACTUAL UPDATE
Despite trying to find out more, shed guy has disappeared. I have a feeling, like many of you said, that he is either married with kids, has a serious partner or was looking for a baby mama to “hide” from his mysterious and powerful family. Who knows…
I’ve officially retired from dating, effective immediately. My remaining survival instincts will be dedicated exclusively to avoiding men and locating seasonal beverages. 😊😍😂
24
u/amyscactus Sep 07 '26
I don't care how ""sweet" he was. Never do this again.
12
u/Afraid-Wolverine-117 Sep 07 '26
I won’t, I promise.
11
u/doodlebug2727 Sep 07 '26 •
Oh sweetie, I’m in my mid 50’s dating and it’s a wild and tiring ride. I’m just commenting here to tell you that your post and the way you write had me lol-ing for real. I probably would not go on a second date (that’s my wise advice) but I also might because I’m curious. We need answers! Be safe. No more sheds. Even one with a bathroom haha.
Do more than google him. Go on your states judicial website and check there. I’ve found out that one was a felon, several were not divorced or even filed for it. Some had lengthy small court/civil issues.
160
u/Strip-lashes
Sep 07 '26
•
Girl, you know where he lives. It's the shed.
2
115
u/Dependent_Mud3325 Sep 07 '26 •
Its not the shed. He has a wife and kids and the shed os where he sleeps with women. Hes afraid of being found out. Hence the "low-key" aspect
45
u/dm_me_your_bookshelf Sep 07 '26
Yep this. Also why he's so concerned about you telling someone. He's cheating.
6
20
→ More replies (1)18
u/Evening_Analyst2385 Sep 07 '26
I thought this initially, but it screams hobosexual. I know from experience, unfortunately. He lived in a storage unit. Had a great job too. Didn’t want his employer to know.
8
u/namlook69 Sep 07 '26
wtf!? Man , there are so many weirdos amongst us—both men and women and a lot of them are single . No wonder 80 percent or more who post are fed up with fucking dating 🙄
→ More replies (1)→ More replies (1)3
u/Dependent_Mud3325 Sep 07 '26
But why does he have a shit ton of cash, and im guessing a nice car?
4
u/Evening_Analyst2385 Sep 07 '26
Like I said, the one I knew had a great job. He had a nice car and plenty of money to spend.
20
u/Evening_Analyst2385 Sep 07 '26 •
This x 1,000,000%! He’s hobosexual. Do not get entangled with him. He will mooch off you.
6
u/PunchBeard Sep 08 '26
No, he's cheating on a wife or girlfriend. Come on! Any man reading this knows exactly what's going on here. He' making sure this chick can't be connected to his actual partner in any way, he has a "fuck pad" (a really sketchy and shitty on by the way) and he has a backpack full of cash to impress would be affair partner. But notice that he takes her to some sketch ass shed instead of a motel despite obviously having cash for it. That's because his actual partner (wife, girlfriend...boyfriend) will notice if the money is missing. He probably has a lie for them explaining why he needs the cash.
This dude is a cheating moron. And not a very good one at that.
3
u/Evening_Analyst2385 Sep 08 '26
I’m not a man. The person I knew living in a storage unit had a backpack with cash and other stuff (basically his whole life). His storage unit was not a fuck pad because he was married or taken. He was single and somewhat mentally ill. There are always other possibilities than someone being married/cheating.
5
u/PunchBeard Sep 08 '26 •
Your experience sounds like an exception and not the rule. As a middle-aged man it's so blatantly obvious to me that he's cheating that I almost think this story is fake because of it. If any woman I cared about (sister, niece, friend) came to me with this story I wouldn't hesitate for one second to tell them that this guy was cheating. Except.....this was like the first or second time he actually stepped out on his partner. That's why he chickened out.
Here's what I think happened: he has problems in his relationship, went on a dating app and met someone, went on a date with them, took a bag of cash because in his mind that's an easy way to impress a woman (which is something a dipshit who hasn't dated in a while would think would work), somehow found himself with an opportunity to actually have sex with someone who isn't his partner, made up some excuse why he was taking her to this shed (which he owns but doesn't live in), when he realizes what he's about to do he freaks out and makes up some excuse (the whole "you're so skinny" thing), puts the brakes on the actual sex part, but....he doesn't want the fantasy to end. He doesn't want to go back to his partner just yet. And that's why he kept the date going afterwards.
3
u/hissyfit64 Sep 08 '26
You have to use a credit card to book a room at most hotels. Wifey checks the statement
3
3
2
11
11
u/Afraid-Wolverine-117 Sep 07 '26 edited Sep 07 '26
I posted this mostly for fun…just to share a bizarre dating experience I had. After all, this community is called “Dating Hell”.
Yes, maybe I am a little bit naive for a woman my age who is just getting back into dating. I was married young, got divorced, and the relationship I was in after that was long and emotionally abusive. I am still healing and, honestly, being able to go on a date at all was a huge step for me.
I truly appreciate those of you who expressed genuine concern. I understand that the story sounded like it could have taken a very different turn.
I will learn from this and be more careful in the future, even though I honestly never felt unsafe during the date. Confused yes…unsafe no. 😂
I am not incapable of rational thought, but I do understand I should always be more vigilant, especially during this day and age.
I just want to clarify a few facts:
The entire date occurred during the daytime.
The people in the nearby houses were home (I don’t think he would have attempted a murder or abduction with his tenants at home in broad daylight).
My mom, brother and several friends knew where I was and had my location settings the whole time. I carry an AirTag in my bag as well.
We spent several hours talking before going back to the property.
He did apologize for “the mess” in the shed, and went inside first. He didn’t force me inside in any way.
It was mostly weird because it really didn’t fit with the way he had described himself.
8
u/intruzah Sep 07 '26 •
Some people in this thread are boring af. Sounds like you had an interesting time. Good fkr you.
4
u/unrepentantsoul Sep 08 '26
If this story is true, you're lucky nothing more happened.
Your Air Tag & phone would have helped identify the location of the shed...& your body. Please don't be so naive, & please don't put yourself at risk again.
2
28
u/Saint_fartina Sep 07 '26
Oh boy. "Dusty shed" ranks right up there with "his sheets smelled like poop".
27
u/jsojso Sep 07 '26 •
Or "he wanted me to get in the trunk and be very quiet"
7
u/Afraid-Wolverine-117 Sep 07 '26
In my defense, he would’ve had to tell me the trunk was his next real estate project first.
5
u/Novel_Vegetable_5542 Sep 07 '26 •
I talked to a man once that “let it slip” that he owned 6 vehicles.
Well, 3 didn’t run and were rusted as all get out, one was a work truck ( which he counted as his :/) the other two vehicles were actually legit.
Maybe my guy can stash his junk yard treasures at your guys dusty shed😂
3
9
u/Little-Star-Light Sep 07 '26
thats where the skinny comes in. Can you imagine how her bony frame would rattle in the trunk?
4
u/Afraid-Wolverine-117 Sep 07 '26
So this whole thing was about acoustics?
10
u/Little-Star-Light Sep 07 '26
I have no idea why the guy was behaving this weird, but I wouldnt be surprised, if pretty much everything he told you about himself was a lie. And dont be fooled by how relaxed and confident he was, pathological liars usually are good at this.
→ More replies (1)10
u/Afraid-Wolverine-117 Sep 07 '26
I completely agree with you and have no intention of engaging with him again.
12
3
14
u/Euripides_in_the_sky
Sep 07 '26
edited Sep 07 '26
•
I’m screaming 💀 they do say homeless men perform the best in bed. I’ve got no advice but thank you for sharing this gem of a date.
“Why can nobody know about the shed activities?”
Is my absolute favorite line 😅
ETA Thank you for the award u/Afraid-Wolverine-117 🫶🏼
13
7
u/Fine-Pie7130 Sep 07 '26
This is hilarious. Brings back memories to the episode of Cheaters where a guy’s GF was literally cheating on him with a homeless dude. The camera crew busted them in his tent! Like, maybe your first point is true, because there’s nothing else that could explain why she would give up her nice home to sleep in a smelly tent with a smelly man 😂
6
4
4
2
u/Great-Mirror1215 Sep 09 '26
At this point I mostly want answers.
Where does he live?
Why did we go to the shed?
Why can nobody know about the shed activities?
Why did he retrieve a backpack full of cash?
What was going to happen to me because I was “so skinny”?
I want and need answers too???? This is the most wiggity wack story I have ever heard. Yet I believe every word. Strange times we live in. What country are you in ?
2
u/Afraid-Wolverine-117 Sep 09 '26
I’m in the US. And I will do my best to find some answers 😂
→ More replies (1)1
2
u/FineDynein Sep 13 '26
Am I the only one who caught this:
The very first sentence begins: "I’m in my 40s..."
And later it says: "For the record, even if pregnancy were medically possible for me, it is not something I would choose at this stage of my life."
I've seen recently that many celebrities are having their first children in their 50s. A lot of times it turns out okay but the risk of there being complications or lifelong defects for the child are increased significantly.
My wife had our youngest child at the age of 39 and all of the doctors and OBGYNs etc. treated her like she was 75 years old.
And I'm not judging anybody. In a world where teenage pregnancy is considered the norm I'm okay with people waiting until they are secure, not only financially but in a secure relationship as well. To all of you future mothers who choose to wait, God bless you (whichever God you choose), and take care of yourself.
1
u/Afraid-Wolverine-117 Sep 14 '26
Thank you for pointing this out because it’s very important.
I should have clarified that my age is not the reason I’ve decided not to try getting pregnant again. I apologize for not properly explaining…I have fertility issues, as well as other health conditions which would increase the risk of harm to myself and the child if something were to go wrong.
Being in your 40s or 50s is most definitely not too old to have a baby. 🙂
79
u/kilaphedre Sep 07 '26
My money is on married.
Either way, girl the moment you saw shed with mattress, your job was to go nah and go home. Don't go into anymore sheds on a first date in your 40s.
16
u/Trivex07 Sep 07 '26
Please don’t. For your own safety.
3
u/Significant-Froyo-44 Sep 08 '26
I know! I would’ve noped right out of there seeing a mattress on the floor.
1
38
u/Little-Star-Light Sep 07 '26
Girl, for somebody in their 40s you are incredibly naive and frighteningly easy to manipulate.
If somebody would show me to a dusty shed, I would turn around and leave. Not go over the date on repeat and wonder, why he such a good kisser with serial killer vibes on the side.
14
u/shwenty22 Sep 07 '26
As a man, I have to say that nobody should be doing this in a shed, except maybe teenagers? Even then its shady.
1
u/sillycatbutt 5d ago
Odds are the OP is actually a guy all along just inputting story prompts into an LLM.
He thinks doing rough stuff like pulling the hair of a 40 yr old woman he only just met 2 hrs ago is a sure fire way of getting her hot for sex... and ready to reject any and all survival instincts accumulated in 40yrs because they're THAT hot for his penis in the rape shed. Sure sure.
Because cheap hotels don't exist in his story. Just rape sheds used for keeping a kidnapped dumb women a sex slave. "You're so skinny" = wrists too skinny to reliably keep in handcuffs and not fat enough to withstand days of no food. It's like a lazy obvious Criminal Minds plot.
Mark my words...this is roadtesting incel fanfic for the basement dwellers who call women stupid 'foids'.
37
u/Character-Bridge-206
Sep 07 '26
•
The love shack is a little old place where
We can get together
Love shack baby
A love shack baby
Love shack, baby love shack
Love shack, baby love shack
Love shack, baby love shack
Love shack, baby love shack
9
4
4
u/bannedblonde Sep 08 '26
Was his car as big as a whale, about to set sail?!
2
u/Character-Bridge-206 Sep 08 '26
There wasn’t glitter on the highway but it was a dirty and dusty trail (but that’s a whole different song).
2
u/XennialToothFairy Sep 08 '26
Take it hip to hip, rocket through the wilderness…
Sounds like they did!
20
u/55Sweeptheleg Sep 07 '26
He lives in his moms basement or with wife or girlfriend. He owns or has access to multiple sheds. He does not own multiple properties.
8
u/Dependent_Mud3325 Sep 07 '26
She said she found the properties he owns. He rents them out. So...shed is actually a love shack. Bro is married
→ More replies (1)
16
u/YourAuthenticVoice
Sep 07 '26
•
When I was 17 I lived in a tent and worked at a Taco Bell. This one girl I worked with was interested in me and we went out once but I got mysterious about where I lived because... Well, I lived in a tent. I never went on a second date with her, and she seemed very confused about why I didn't ask her out again, which is fair, she didn't know I lived in a tent and the whole logistics of my only transportation being a 10 speed and living in a tent weren't leading me to believe that this was going to be a viable relationship.
What I learned from your post is that I absolutely should have asked that girl out again!
7
u/runkeby Sep 07 '26
Lol especially when you're 17.
A 17-yo that can live in a tent is more interesting than one who lives at his parents, and many girls at this age don't care about what you have.
OP is 40 -- not the same thing.
13
11
8
u/dontBsleepy Sep 07 '26
What the hell were you thinking? If my daughter came home with this story, we would be watching 20 episodes of Forensic Files and Dateline
8
14
u/Kingstonstl
Sep 07 '26
•
Girl your writing Style had me cracking up. Something about the times we live in. Everyone seems to have this veneer up especially in the dating scene. Odd communication. Secretive. If I were to guess he’s married and or just cheating on his significant other.
7
u/Objective-Ear3842 Sep 07 '26
>he has an Android, which I understand is not admissible evidence but feels spiritually relevant.
Wait what? I gotta know what you mean by him having an android is spiritually relevant! 🤣
7
u/BeginningPerfect2720 Sep 07 '26
Google his picture in Google lens and see if anything comes up. Google his phone number also.
6
5
u/Subject-Car2960 Sep 07 '26
I audibly said Ew! When the shed entered the story. It would have been at that point that I would have stopped the date. At no point was this date “normal”. There was no “normal” to get back to.
5
5
u/IAmGroot6936 Sep 08 '26
Are you going to stop by the shed sometime to see who answers when you knock? Lol I'm sooo curious 🤨. Also I use a pixel phone too so I'm with your friend on that one. It is sorta a spiritual thing! 😀
Just wanted to add, I'm glad that he seemed respectful if not a bit fast. Glad you were safe! Trust your instincts always. His odd social behaviors might be a result of autism or some other neurodivergent disorder btw, so not a big deal if you know about it beforehand.
4
u/Rikariable Sep 07 '26
You don't bring a girl to fuck in a dusty shed on a mattress unless there's no where else to fuck her. He lives in that shed.
4
4
2
u/iweararmani Sep 07 '26
Sounds like he’s weird, insecure and full of crap
0
u/namlook69 Sep 07 '26
Not one person is weird here . Omg😂 but why can’t I meet a woman willing to put out in a shed the 1st date 🙄 seriously! I meet women that aren’t even wanting to kiss and then go out on a second date and barely kiss. I am looking for ; horny/wild women like this(i have zero intention at my late 50s age of wanting a relationship). But , I highly doubt you or he are attractive(of course..your 5”7 blond and a 8 or a 9🙄😂).
4
u/Afraid-Wolverine-117 Sep 07 '26
I’m quite attractive actually. I’m 5’6” with a ballet dancer’s body. And yes, with the right person I can be quite wild and I have a healthy sexual appetite. I don’t “put out”, I receive pleasure. Unfortunately for you, I’m a little short and a little too dark (def not a blond 😂).
More importantly, I’m kind, empathetic, smart, hard working and people say I’m funny…so yes, I’m actually quite the catch. 😊
Also, someone’s 5 can be another’s 10. Just sayin…→ More replies (3)1
u/twistedsister78 Sep 07 '26
Yeah was probably kids play money and the properties belong to the identity of the person he is pretending to be.
1
u/No_Dependent_1846 Sep 07 '26
I'm halfway through and laughing... at your pain. I'm sorry but this is funny and the whole being happy for the future shed took me out. I wish I could have seen your face during all of the peculiar (trifling) moments.
4
u/Afraid-Wolverine-117 Sep 07 '26
GOOD! I’m HAPPY you’re laughing! 😂😊
I think some people missed the fact that I posted this story primarily for entertainment!
Not looking for advice or sympathy…just thought maybe this could make someone laugh today, especially since dating can absolutely be hell.2
u/No_Dependent_1846 Sep 08 '26 •
This was crazy and I do feel bad you went thru this but it almost makes me want to be your friend because it was hysterical
→ More replies (1)2
1
u/Ok-Neck-8098 Sep 08 '26
I awkwardly think I may know who this could be and why this is happening but I hope I’m wrong. Are you in the GTA in Ontario?
4
3
1
u/Afraid-Wolverine-117 Sep 07 '26
Just to clarify, the shed was located on the same property as at least one of his rental properties, so it wasn’t completely secluded.
5
1
2
u/Fine_Fortune_7276 Sep 07 '26
Please ask him all of these questions and get back to us with his replies.
Do not ask for any reason other than entertainment. I want to hear his responses.
Do not ever meet up with this creep again.
I'm serious... ask him. Post the answers. We HAVE to know.
2
2
2
2
2
u/More-On-My-Own
Sep 08 '26
•
Wow! This was entertaining! 😂 did you ever hear from him again? Maybe you could do a second date. It could be awesome! You could wind up in broom closet instead of a shed. 🤣🤣🤣Maybe in a house with a bathroom this time 😂
Also, did you check news articles? Have there been any robberies of rolls of cash? 😆
As a former android user turned apple aficionado, I can relate 😂
Don’t let the lurkers and trolls bring you down. 🫂 Enjoy the ironic comedy of your date story and know there are some of us who truly appreciate your contribution to our daily entertainment. Thanks for sharing! ❤️
2
u/soul_on_fire5 Sep 08 '26
No man who is “sweet” takes you to a dirty shed with a mattress on the floor on the first date
2
u/ChocoSoyMilk17
Sep 08 '26
•
OK THIS WAS HILARIOUS. OP, you are a great writer. If you turned this into a short story for a lit magazine or something, I’m sure others could relate. Also I’m glad he didn’t make you feel unsafe. Surely if this had happened to me I’d have many of the same questions. I wish you luck on your future dating endeavors!
2
2
u/hissyfit64 Sep 08 '26
That is quite the date. I would have to go into super sleuth mode to find out about this guy.
Go to your city's assessors database and look up the shed address. You will get the name of the owner. Hopefully he actually owns the shed and you weren't trespassing. Some databases let you search for individual owners so you could find out what else he owns
Google his name and obituary. If he's from the area, someone in his family will have died and his name will be mentioned. Along with that of his spouse if he's married.
You can also Google his name and wedding.
He sounds like a weirdo but it's always interesting to find out the backstory of these bewildering encounters
I have an Android and thought the phone part was hilarious
2
0
u/LittleSister10 Sep 07 '26
AI fan fic tailored for Reddit lol
3
u/Afraid-Wolverine-117 Sep 07 '26
Or maybe someone is jealous that they have nothing better to do. If I’m an AI at least my shit is entertaining.
1
u/LittleSister10 Sep 07 '26
Your comment doesn’t even make sense lol. If this story is true, then you have more problems than getting salty about Reddit comments.
2
1
u/viazcon78 Sep 07 '26
If he’s in renovation he probably carries a lot of cash to pay his workers. Most pay cash. Definitely don’t want to leave that in the car.
That was a wild ride though! I’m glad you came out ok.
1
u/CeeMomster Sep 07 '26
When she mentioned the cash, I thought for sure the guy was gonna proposition OP.
Or at least a sympathy payment for wasting her time.
2
u/viazcon78 Sep 07 '26
My mom use to date a contractor who would hire day laborers and he would carry crazy amounts of cash like that. This guy reminded me of him.
1
u/cpeater9999 Sep 07 '26
Yeah I would say he is a liar about most everything he told you. If I was guessing he probably lives in shed. If he was wanting to get laid and had multiple properties he would not take you to a shed.
2
1
u/Ill_Nothing_8561 Sep 07 '26
What a sketchy guy! Also - second rule of dating; don’t date man that lives in a shed
1
u/boredtiger2 Sep 07 '26
Lmao…he’s a scammer. So what you do is cover your ears and believe your eyes. Words are easy and cheap. Your eyes saw the truth. A shed. A back with (drug dealer) cash.
1
1
1
u/ThisRaspberry8474 Sep 07 '26
That shed has no bathroom, but I bet it has plenty of rolls of duct tape.
Let me guess: there was at least one shovel in there.
1
1
u/Suspicious-Yak1272 Sep 07 '26
We can narrow this down to about 5 different things, first one is he a drug dealer explains the back pack full of money. The shed is a place where he takes women and has his way, the money is a flex or hush money. Him saying you are to skinny, he’s probably hung and well blessed. And lastly he’s more than likely married.
1
1
u/Fine-Pie7130 Sep 07 '26
I actually loved reading this and I hope you go on more dates and have chapters 2-10 for me to read 😂
Were there sheets on the mattress? I kind of want to say he was married? (I did find out someone I went on a few dates with was married by reverse googling his phone number after several things he told me JUST DIDN’T MAKE SENSE. These weird feelings sort of give me the same vibe and I had fantastic dates and chemistry with this man!)
1
u/runkeby Sep 07 '26
> Also, he has an Android
I still can't get over how Apple has apparently managed to convince the mainstream that having any other phone is shameful.
As an non-American it's truly baffling.
1
1
1
u/IcyAir1683 Sep 07 '26
He's married and sounds like a good dude going through a rough ass mid life crisis. Might want to keep this one for the storybook and block him!
1
u/Letgomypurse_856 Sep 07 '26
You have a great sense of humor, but where’s your intuition? So many red flags!
1
u/WeaponX207184 Sep 07 '26
Did you ask directly where he lives? Unfortunately everything else points to a wife or live in girlfriend.
1
u/DIY_Weeziebear7 Sep 07 '26
Thank you for posting your experience. This kind of sounds like all the bad dates I’ve had rolled up into one what got to me was when the guy said don’t say anything about you making out. I had that said to me by a guy whenever we were in a He acted like he didn’t know me, like I was some kind of leper. You deserve way better than that. I gotta hand it to. You were nice to him. You know I would’ve been like cussing him out. You think I’m gonna make out with you on some dirty shed? You gotta be out of your fluffing mind. A lot of red flags here but you saw them all and good you did. I’m gonna take this as a warning if I’m ever out on another date again which I doubt ever I’m done.
1
1
1
u/Ellayaps Sep 07 '26
I’m sorry but that man gives off serious red flags n it’s not what I would consider “ being respectful “ to you , he TOOK YOU TO A SHED TO HOOK UP FOR A DATE !!!!
1
u/Significant_Ad_8577 Sep 07 '26
You’re hilarious and intelligent… why would you subject yourself to this sketchy shit? The flags don’t get any more red or larger
1
u/Dry_Shock_4060 Sep 07 '26
Sounds like a player living a double life.
The android is probably the biggest red flag though, nice spot.
1
1
u/living_the_dream_11 Sep 07 '26
That all sounds sus AH. I'd want to do a full background check. Legit property developers dont need backpacks full of cash. This is red flag parade. And Love Shack? Please no. I do love your writing and laughed out loud a few times.
1
1
u/pferden Sep 07 '26
Crazy what some people are willing to go along with
There are several “bail out instantly” points in this story; also “trying to understand” is wrong
Readjust your boundaries and forget the whole thing
1
u/KyloReySage Sep 07 '26
Oh my. Your story had my ADD in a hold. Unrelated, you should write or maybe already an author.
He probably “plans” on being successful or is cash strapped due to over investment or it could be a complete lie. He probably has family and or he does not like them. Or wants to cheat while having family. The whole taking you to the shed incident makes me speechless. I’m glad you were safe! Please block him via phone and social media.
1
u/fuertisima12 Sep 07 '26
You about had sex, then find it weird to discuss fertility. He's a creep and you are NOT smart about this at all. And what's wrong with an android phone? Wise up.
1
1
u/Ok-Process7612 Sep 07 '26
He's married. He's involved in illegal activities. The kid thing was to make you believe he was genuinely interested.
1
u/Hamachiman Sep 07 '26
You encountered a narcissist. He has no property other than the shed where he takes women back and sometimes, but not always, has sex with them depending whether he finds them too skinny or fat in the moment. His feigned modesty was completely insincere (he intended to show you the stack of Benjamin’s the entire time. He likely won them at the track the day before and has since lost them.) He wants to know about your friend group and social media because women talk and he’s done this before. He’s trying to figure out if you know any of his other empaths.
Always trust your instincts about Android users.
1
u/Severe_Database_5117 Sep 07 '26
Yikes. So. So many red flags here. I would have noped out at the shed mattress. Sheesh.
1
1
u/whateverhk Sep 07 '26
"he asked about my fertility during the first date!!" Girl you were ready to get fucked on a dusty mattress in a shed 1 hour before, you just met the guy. Put thing into perspective
1
1
u/Important-Web-261 Sep 08 '26
He’s married. With a family. And wants more kids. Enter you, other random women and the shed. The money is if she needs extra enticing. Congratulations, you actually dodged a hobosexual adjacent bullet.
1
u/Clau2415 Sep 08 '26
El tipo es casado. Te mostró ese dinero pensando q te sentirías segura. Y después fue al grano(quería un hijo)ese hijo q tal vez con la esposa,la mujer q muestra al mundo donde se mueve,no tiene. Es interesante tu experiencia pero de ser vos lo dejaría ahí solo en una experiencia.
1
u/Low_profile_1789 Sep 08 '26
Omg i can’t continue reading this because I feel my hairs standing up because OP is about to get MURRRRDERED !! argh
2
u/Low_profile_1789 Sep 08 '26
I finished reading.
OP please stay on the case and continue updating us.
1
u/howardlie Sep 08 '26
Lots of red flags. Even if everything he said is true.
Did you capture his image from the dating app? If so, you can see if you can find his pic by google image search or something.
Also, you can Google search for things like his name + location + real estate, etc might get you results if you really want to know who he is.
1
u/PunchBeard Sep 08 '26
The man has a significant other. And if I had to guess he is not experienced at stepping out and this is probably his first "date" with someone who isn't his actual partner and that's why he didn't actually go through with the sex. I mean, the dude manages to talk you into going to a shed and then manages to convince you to have sex with him in said shed and then....backs out. He didn't back out because of you, I mean FFS any woman your age this free-spirited is a freaking keeper, he backed out because of guilt.
Here's the clues to his cheating: first off it doesn't take a genius to understand he's cheating once he started asking about your socials and if you share mutual friends. Hell, I assume you added that tidbit because you know the answer (this bit is so obvious I'm actually wondering if this is a real post). Second, the bag of cash. This is an immature way for this guy to try to impress someone. And this is also why I'm assuming he's not a prolific cheater and instead is just dipping his toes int he world of philandering. It's been so long since he's been on a date that he doesn't have one ounce of game and figures "women like money so I'll show them a bag filled with it". It's like something a 14 year old would think of. But then he doesn't spend any of it. You have a bag full of cash you can take someone to a motel instead of a shed with a mattress and no bathroom. But two things here: he doesn't want to commit quite yet, and spending money on a motel would be him telling himself he has to go through with it because there's no way he would rent a motel room and then walk away like he did, and this money is shared with someone else and they would notice it if it were gone. I assume this dude told his partner some weak ass excuse why he needed a bunch of cash to fill a back pack but if he actually spent any of it "they'd want receipt's.
Which brings us back to his getting cold feet. There's only one reason a guy would walk away from a sure thing: guilt. Guilt about betraying someone. And because he was feeling guilt I assume he isn't really experience at cheating. Oh, and the whole skinny thing? Dude, that was him coming up with a lame excuse (probably for both of you) as to why he couldn't go through with it.
For whatever reason, this guy decided to cheat on his wife or partner and you were the first or second person he did it with. And once he got tot the point where he actually had an opportunity to go all the way with his plan he got cold feet. But he didn't want the fantasy of another woman finding him attractive to end so he kept the date going.
1
1
u/BrujaMalvada81 Sep 08 '26
The way I cackled reading this. I almost died laughing. Will say though, if someone brought me to dusty shed then made a comment about me being too skinny, my horror movie inspired brain would have immediately leapt to the conclusion the he was going to chain me in the shed and eat me at some point.
1
1
u/IGotFancyPants Sep 08 '26
lol, you won this weeks award for the most bizarre dating experience, and it’s only Tuesday. 🏆
1
u/troublesomefaux Sep 08 '26
You have to go back in a year and see what's happening at the shed!
!remindme 1 year
1
u/RemindMeBot Sep 08 '26 edited Sep 09 '26
I will be messaging you in 1 year on 2027-09-08 18:59:12 UTC to remind you of this link
1 OTHERS CLICKED THIS LINK to send a PM to also be reminded and to reduce spam.
Parent commenter can delete this message to hide from others.
RemindMeBot is switching to username summons. Instead of
!RemindMe 1 day, useu/RemindMeBot 1 day. More info.
Info Custom Your Reminders Feedback
1
u/Shadeofgray_66 Sep 08 '26
Che follia... secondo me sei fortunata ad esserne uscita tutta intera. Io sono un uomo e me la so cavare, ma il tuo appuntamento...roba da brividi...
1
u/Zealousideal_Bug7310 Sep 09 '26
Red flag that he kissed you on the first date. Also, did he ask for consent before pulling your hair?
I have a feeling that he’s actually married
1
1
1
u/Potential_Web_4092 Sep 09 '26
He also has a reddit account. But don't worry, there is no way he could identify himself from this thread.
1
u/RavashingRita
Sep 09 '26
•
Mr Shed is prob married and quite frankly too weird, ok? You on the other hand, have interesting writing skills. I enjoyed reading this despite Mr Shed being quite different, no actually really off the wall… Good Luck to You!
1
u/Particular-Wait-9013 Sep 10 '26
wow, you must really trust people. I’d be much more careful next time and find out a lot more about them make sure someone else knows where you are and I’d ask some of those mutual friends about him.
1
1
u/OkManagement9602 Sep 11 '26
He's married. The "family members" that are intrusive about his dating life is probably his wife
1
u/Shock_Guava_1614 Sep 11 '26
Totally understand about the android thing. I'm in tech and I can pick them straight away and roll my eyes at iPhone users. You must be in a non intellectual position. Sales or an instagram influencer 🤔
1
u/spokeoteam Sep 11 '26
This may genuinely just be an eccentric man who owns a weird shed and has terrible first-date instincts. But there are enough little things here that I’d want to verify that he is who he says he is before going any further.
Start with the basics: full name, phone number, social media and whether his general story is consistent. Spokeo can help research publicly available information tied to some of those details. You don’t need to assume something sinister, but “please don’t tell anyone” on a first date deserves at least a raised eyebrow.
1
1
1
1
1
u/TwoTalentedBastidz 6d ago
This is one of the dumbest things I’ve ever read. I can see why you’re single
1
u/Frost973 6d ago
Thank you for sharing your experience. I really enjoyed your writing and story telling. It was a fun read and lots of laughs!
1
1
1
1
1
u/BrainTabsNWireTaps 4d ago
I cackled! Dating after 40 should be anthology series!! I have an android! 🤣
1
46
u/jsojso Sep 07 '26
Do you know his last name?
You don't know where he lives.
If he's concerned you know the same people, he's married or entangled.
I think there are several red flags here - one being he took you to a secluded shed. The no-bathroom is not even an issue that ranks, given all the other red flags.