TIFU by making a bet with my college roommates

TIFU by making a bet with my college roommates

EDIT: Long story, but worth it.

This happened a few years ago....

College is that magical place in life where you can “start over.” Wipe the slate clean of all the shameful shit you’ve done up to this point and truly become a new person. ‘Spread your wings and fly’ they said. Talk to anyone and everyone. Rivy, Dan and myself were freshman year roommates, and we did just that.

The dorm hall was a long chain of newfound friends. Some of these people would fizzle out over the next four years, others I’m happy to say I can still call my best friends. We were a tight-knit hallway. Everyone liked everyone and we all got along.

Our room was in the dead center of the hall. We’d leave our door open and extend an invitation to all our hall mates to come and chill. Whether we were smoking pot, playing video games, watching TV or just kicking back, there was never a dull moment or a bad vibe.

Then Angelica moved in…

It was halfway through first semester when a bed opened up in our friend Brenda’s room. Angelica was on a transfer list. Brenda was a one of our closer friends, so we told her to bring Angelica over to hang for a night, as to welcome her into our little community.

Angelica was a zero-fucks-given half Italian half Lebanese girl with a crippling case of the crazies. She talked with a thick New York/Mona-Lisa Vito accent. Ya know, “Fuck you, fuck him, fuck her and fuck anybody that looks like her.”

“Do you smoke weed?” Dan asked.

“Yea,” she responded

“We were gonna go smoke if you wanna thrown down.”

“I ain't got anything.”

This wasn’t a problem at first. We were happy to welcome a ‘new friend’ and didn’t mind smoking her up. We went outside, sat in our favorite smoking spot and rotated a pair of spliffs. Angelica was one of those, ‘Never shuts the fuck up when their high,’ kind of people. I myself occasionally suffer from the same side effect, but we’ve all got our pitfalls.

Granted, everything she said was a little humorous. I’d shut my eyes and picture Marisa Tomei, but if Marisa Tomei had just packed a fresh lip of Copenhagen Wintergreen.

We ended up back in the dorm room, turned on our favorite ‘high’ channel, TruTV , and were happy to find that a new episode of Hardcore Pawn was airing. But oh wait, Angelica wouldn’t stop talking.

“This shit’s all fake. They stage everything. How can you watch this? This is gay. Let’s smoke more. Do you have any booze?”

Yea, I know the show is probably fake. But let me a pretend for a fucking minute, will ya? No, we aren't smoking again, it’s been 5 minutes, and no, you’re not having any of our booze.

The Hardcore Pawn marathon ended. A normal human being would take the hint that everybody crawling into bed and turning the lights off meant the party was over and to kindly get the fuck out. Angelica was not a normal human being. Brenda tried to get her to leave, but she insisted on staying. Rivy and I didn’t know how to handle the situation, so we just rolled over in bed and tried to fall asleep. Dan left the room to shit and brush his teeth and hoped that Angelica would be gone by the time he returned. But oh was he mistaken. Once Dan left the room, Angelica climbed up in his bed. Brenda admitted defeat and left.

Now, Dan and Rivy had bunk beds and Dan had the top bunk. My bed was across the room and elevated over my dresser. It was as if I had top bunk, but there was nobody under me. Basically, I could look to my right and see Dan’s bed.

Dan returned, climbed up to his bunk and laid down next to Angelica. Complete and utter silence ensued for the next twenty minutes. I’ll never forget the conversation Rivy and I texted each other.

‘Are they…’ –Rivy ‘What? – Me ‘Fucking?’ – Rivy ‘Nah, Dan’s got standards.’ – Me

That’s when Angelica hopped down from Dan’s bed and left without saying a word. Dan then hopped down and turned the lights on. The three of us clearly had way too much to say to each other, but Dan, standing in the middle of the room, had the floor.

“I fucked her,” he said with a wide grin.

“What the fuck?” Rivy and I exclaimed.

“Got her to leave, didn’t I?”

“Well, yea… but why?” I asked.

“Dinner was on my plate and I had to eat,” Dan responded. To this day, that is still in my top 5 quotes from college.

Angelica kept coming around. In her mind, we were best friends. I try to give everyone I meet a fair chance, but holy fucking shit was this girl annoying. We decided, okay, one more chance. Some friends of ours were throwing a party one weekend at a house off campus. We thought we’d bring Angelica along in the hopes that she would meet new people and make other friends.

The party was actually pretty fun. I was the only one in the group with a car so I usually ended up being the driver in these situations. I didn’t mind it thought. I was never one that had to be drunk to have fun. The same can’t be said for the others thought. Especially poor Brenda. I’ve never seen her as shit-housed drunk as she was that night. Brenda could usually hold her own, but it got to the point where I became concerned. I gathered the troops and said that the party bus was leaving. Rivy and Dan understood. Angelica though, insisted on staying. She said it was Brenda’s fault for getting too drunk and she wasn’t going to let her ruin the night. Now, she may have been right in the sense that it was Brenda’s fault, but you don’t treat your “friend”/roommate like that. I told her we’d leave her there if she didn’t come now. After a few more minutes of arguing she finally came with us. Poor Brenda was slouched over in the car in complete drunken misery. It was only a ten minute drive back to campus, but to her it must have felt like an eternity. We finally pulled up next to our building and Rivy and Dan helped Brenda out of the car. If you’ve ever tried to lift dead weight, you’d know that it’s not as easy at it sounds. Dan and Rivy ended up dropping Brenda on the ground. Thankfully she didn’t hit her head or anything. As for Angelica? She left and walked back into the building and offered no help with her roommate. We made it back to their room, but Brenda was too drunk to put her security code in. We knocked and knocked. We knew Angelica was in there, but she didn’t answer. Finally, she ripped the door open.

“What! I’m trying to go to bed!”

“Jesus Christ, Angelica, help us get Brenda in her bed!”, Rivy hollered.

“No, she’s going to puke and I can’t sleep if the room smells like vomit!”

“What the fuck is wrong with you?!” we answered back.

The three of us barged past her and put Brenda in her bed. Dan moved a trash bucket next to her and we left.

This was the last straw. No more chances. We didn’t know how to get a person like Angelica out of our lives without repercussions. How do you tell someone you don’t want to be their friend? Especially now-a-days when everyone’s got their safe spaces full of green grass and rainbows?

The three of us all felt the same way about Angelica. The three of us also felt the same way about Jack Daniels. We decided to make things interesting. A bottle of Jack would be awarded to the roommate that could go the longest without speaking to Angelica. The game was on.

We’d go to absurd lengths to avoid this girl. Our friends Mike and Brian lived at the other end of the hallway. In order to not risk Angelica walking out of her room as we passed by, we’d go up a flight of stairs, down the 2nd floor hallway and then down the stairs to the other side.. One time I was coming back from class and saw her approaching me from the other end of the hall. I knew I couldn’t make it back into my room without passing her. Now, I really wanted that Jack, so I improvised. I pulled out my phone and faked a conversation as I walked down the hallway. I made sure to sound invested so that when Angelica eventually said ‘Hi’, a simple head nod from me sufficed as a response. The high council allowed this “contact” to slide, as it did not break any bylaws of the bet.

Every so often, Brenda would fill us in about her time spent with Angelica. Not only did the girl drink almost 24/7, but she also had a gross dependence on prescription pills. Angelica would wake up and pretty much stick a straw in a bottle of bur-nasties (Burnett’s vodka) , and down pills like breath mints before going to class.

We made it 3 weeks until shit hit the fan.

One night, around 11:00pm, Angelica came pounding on our door.

“I know you guys are avoiding me! I told the RA’s you smoke pot and are bullying me! I told them about all the drugs and alcohol in your room!”

Great, she was once again ruining another new episode of Hardcore Pawn. We remained silent. I snuck up to the door and looked out the peephole. There she was, standing in front of our door, hollering and pouting, then hollering once again, followed by more pouting. We didn’t know what to make of her threats. Did she actually rat us out or were they just that, threats?

Then she texted Dan, ‘I was on antibiotics and you came inside me.’

He freaked the fuck out. She had assured him that she was on birth control that fateful night, but apparently she was on some kind of antibiotics that could potentially cancel out her semen slayers.

“Fuck this bet,” Dan said. He ripped the door open, but she was gone. He stormed out of the room and down the hall. Rivy and I just looked at each other.

“And then there were two,” he said.

Dan came back a few minutes later. He was pacing around the room, looking up different birth controls and antibiotics on his computer. I had never seen the poor kid so worked up. He certainly was not ready to be a father.

“Why the fuck wouldn’t she tell me she was on antibiotics! She’s fucking crazy!”

“What happened down there?” Rivy asked.

“She’s screaming at Brenda and Ashley (Ashley was their third roommate) about how she doesn’t have any friends. Somehow, it’s everyone else's fault that she’s fucking insane.”

Now, we liked Brenda and Ashley, after thinking about it for a few minutes, we decided that our silly bet wasn’t worth all this stress. We walked down to their room and thought it would be best to talk things out.

Talk was probably not the best word to use. We tried to ‘talk’, but Angelica and Ashley continued to scream and holler at each other. Ashley would tell Angelica how crazy she sounded and Angelica would counter with how everyone is always mean to her and everyone hates her.

I tried to step in simply said, “Look, it’s not that we hate you. We just aren’t destined to be friends. If we can just agree to leave each other alone then we’ll all be better off.” I thought that was a rational argument. I was wrong. My suggestion was met with more screaming and swearing. I could see a group of shadows outside of the door. I looked out the peephole to see our entire hallway gathered outside Angelica’s room. I opened the door and stepped outside.

“What the fuck is going on in there?” our friend Mike asked.

I told him as much as I could. A few people from upstairs had joined to see what all the fuss was about. I’m someone who believes that everyone’s business is their own, and these kids from upstairs didn’t need to know what was going on.

“So who won the bet?” Mike asked. I laughed and said it was off. We’d all be splitting the bottle that weekend.

I went back into the room to find that the argument had gone nowhere. Eventually, Dan, Rivy and I decided that this wasn’t worth our energy. It was 1 in the morning and we all had class the next day. We went back to our rooms and passed out.

The next day, after class, Brenda came knocking on our door. We let her in and made sure Angelica was nowhere in sight. She informed us that after we left, Angelica and Ashley continued to fight. Apparently while we were sleeping, Ashley’s boyfriend ended up driving down from the city and joined in the screaming match. Furniture began to be thrown, death threats made and police called. The boyfriend allegedly put his head through a mirror (because that’s one way to win an argument). Ashley moved out the next day and now, poor Brenda, was left to deal with Angelica, on her own, for the rest of the year.

Our RA came knocking on our door later that night. She said that she was informed of illegal substances in our room and was going to have to search it. I guess Angelica had ratted on us after all. We had thankfully smoked all the weed earlier that night, but our beloved bottle of Jack Daniels (and other booze) was ripped from us before we ever got to crack it open. The RA sat us down and questioned us about the whole situation. We explained to her that Angelica refused to leave us alone (There was obviously never any mention of the ‘bet’) and that she really isn’t a nice person. The RA lectured us about the dangers of bullying and we just had to sit there and pretend like we were the assholes. We were ultimately written up for alcohol possession, had to pay $100 each, were forced to take classes about the dangers of alcohol abuse and had to go in front of a residential board for conduct hearings. Our alcohol safety classes/hearings overlapped with our actual schedules and we ended up missing a handful of important classes because we were “alcoholic bullies”.

TL:DR A crazy girl moved into our dorm hallway. We made a bet to see who could go the longest without talking to her. She snaps and winds up ratting us out for weed and alcohol in our dorm room. In consequence, we were written up, paid a fine, had to go to alcohol safety classes, and conduct hearings which made us miss important class time

UPDATE Thank you all for appreciating this tale of fuckery! Most of you are asking what happened to Angelica? Well my friends, there is a part 2 to this story that following summer! Once I get all the facts collected, I will write it and post it to where it is appropriate!

No, Angelica did not become pregnant. Her spunk warriors tracked down the many squirming baby cells and slain them like the foul beasts they were!

Yes, we have TONS of crazy stories from college and our lives that we post at our own convenience. I must respect TIFU rules and not self-promote, but if you search around you will find a magical place filled to the gills with marvelous stories of mayhem, tomfoolery, and much more!

Thank you to the two kind souls who gilded us as if we were the Knights who thrashed the sperm goblins before they breached the Egg Kingdom! We are forever in your debt!

If anyone has any questions and need them answered fast, don't hesitate to PM me! I'm tying my best to reply to every comment but it is tough....tougher than trying to get back into Hardcore Pawn again!

Thank you everyone!

I've never read such a long TIFU. She sounds like a nut job.

EDIT: Still a great read, very entertaining.

Good read. But Honestly fuck Angelica

Just not when she's on antibiotics.

"Dinner was on my plate and I had to eat" Best quote I've heard in a while haha. Great story man

Sorry for the length. If I didn't really write it all out, it would have made it look like we were the assholes lol

It blows my mind that people think that they're being bullied just because others dont like them.

It's like me saying that Chris Pratt is a bully because I wasnt invited to his birthday.

And wear a fucking condom

i enjoyed reading this lol kept me on ur toes

Thanks! There is more to the story along with little side plots here and there. But I figured I'd save those for the comments.

$100 fine, each?!

Did the RA buy some nice weed for themselves or something?

Oh yea, she was nuts. You should have saw my friend Dan once he found out she was on antibiotics. Depending on what they are, it can interfere with contraception. Lucky for him, she was fine. I remember walking down the hallway and heard Angelica talking to her mom about it. She said, and I quote. "This kid keeps freaking out on my mom. I let (insert frat dudes name) cum in me 2 weeks ago and I'm fine! Dan should shut the fuck up about it!"

Who talks to their mother like that? lol

Moral of the story: Always wear a condom, especially if she says you don't have to.

We tried our best to give her a chance, but she obviously failed. Everyone should have seen the red-flag as soon as she transferred to our dorm. When we spoke with the RA we told her that we didn't like her and we had every right to not associate ourselves with her.

In my top 10 quotes!

Yeah antibiotics and birth control don't mix. Found that out the hard way and now have a 16 month old to show for it. His freak out level was completely appropriate.

I prefer love-making condoms.

The money goes to student conduct or something

The 'too much specific info' train left the station long ago.

i jus cant believe a pillhead called the RA on u lol so petty

I can't really divulge too much info, but she ended up dating one of my close friends that following summer. That's another story in itself!

I was lowkey thinking one of you crazy bastards were going to try to double down and win the bet by having sex with her and still refusing to talk to her the whole way. That'd have been something.

Nope, he didn't.

I'm surprised he's not a father of 7 with space aids.

This was a great TIFU. Might be a long read but very entertaining throughout. Thanks!

Want to know though, what happened to Angelica? Do you have to live with her through the conduct hearing and/or for the rest of the year? She sounds pretty crazy, that'd be aweful. Also do you have any idea how her life turned out?

Hey! You said it was in your top 5! OP is a phony!

So, more weed for the student conduct or something?

I stopped halfway through reading this because something was happening at work. I came back and finished reading and was like "where is the Revenge part" then I realized this was a TIFU and not a ProRevenge.

Great read though


It was quite the scene.

I live by those words

I wish you told me this years ago

Dinner's on my plate I have to eat

Having a close enough relationship that you can have frank conversations about sex is good. But, having to hear your daughter talk about a guy cumming inside her is ear bleach material. Class act!

It's in Gucci's top 5 lol

Oh boy, you know a story is going to be good when the main antagonist is named Megan.

You should wear a condom regardless of them being on birth control. #1: You have no way of knowing that they actually are on said birth control and #2: Birth Control doesn't prevent STIs. Hope that Dan took a lesson from all this!

Takes me back to my freshman year of college. So there was this girl named megan...

If it's his 3rd favorite quote, both are accurate.

This is the first time I ever read a TIFU this long.

Worth it

I love your friends quote, haha.

To be real tho, I think your fuck up was not being straight with her. Being ghosted can make a person go nutty even if they're otherwise normal. So, double nutty for Angelica. You probably should have just talked to her like normal but been curt... if she asked to hang out, tell her you're not interested. If she asked why, it's because of the way she treated a sick Brenda in her time of need.

We are cousins!

Your wife's name is fuck?

Nah, he pretty much kept raw dawgin'

What happened to her?

Ashley was the 3rd roommate. She was dealing with a bunch of emotional problems and the whole ordeal with Angelica was the last straw. She left the college the next day. Brenda and her were kinda like friends just because they were roommates, after freshman year, they both bounced their separate ways.

For the remainder of the year, everything kind of cooled down. My roommates and I never really held hard grudges at all, neither did she. I think that would be different if she knew that not talking to her for three weeks was based on trying to win a bottle of Jack! hahahaha

She isn't pregnant with your friends kid is she? Because lord knows this is why you don't stick your dick in crazy.

Yes, she was attractive.

You guys are such bestest friends that you share a reddit account? That is awesome

Entirely worth the read. Interested in those sub plots you teased in the comments.. how was Ashley involved in all this? Did Brenda and Angelica ever fight after all that? Did you just ignore Angelica the rest of the year? I need more details!

a bunch of squares I tell ya!

It blows my mind that people would want to hang out with others who don't like them...

I mean this isnt high school, this is college. There WILL be people who share the same interests as you

We mod a sub where my cousin and I post all of our crazy stories and encourage others to do the same. Check it out! We also write screenplays so hopefully one day you'll read something here and see it on the big screen!

"Dinner was on my plate and I had to eat."

Thank you for sharing this comment.

"I can't get pregnant mom I'm a semen dumpster, what's there to worry about?"

Who doesn't wear a condom when they have sex with strangers?


I'm still amazed underage drinking in college is even a thing.

This is the most insane part of the entire thread.

Episode 2 will come soon. I won't be able to post it here though so stay tuned lol

I'm amazed you didn't explain you'd been actively avoiding this young woman and that she had been sucking down alcohol and pills before classes.

Makes me wonder why she was on the antibiotics in the first place.


more money for the school execs...

Alright boys, close the thread down, we got what we came for.

So did Dan.

Oh thank God. I got to the end of the story and all I kept thinking is, "But what about Dan!?!? He broke the Cardinal rule of not sticking your dick in crazy! Does he have to pay the ultimate price?!?! Where's episode 2 of this crazy story!?"

Yes and no hehe

Why don"t you make a series out of this? You are a great writer. No business like show business, eh?

"If everyone smells like shit, chances are you are the asshole." I don't think she was aware of this.

Okay that all makes sense now, I was sort of messed up seeing how you were saying you were both Rivy but also in the story saying Rivy,Dan and myself

For weed?

Technically it could be both, but the consequence was heavier than the reward.

Okay dude...why did you never just tell her you don't like her? Before the 'bet' just be like "Listen I don't hate you but I don't want to be friends" I did this with my annoying person and after calmly explaining shit out we parted amicably and stopped hanging out.

Why drag that shit out and drive the other person up the wall? Especially someone you know has a crazy streak?

This is funny because a friend of mine is now on his 3rd girl named Megan, all getting progressively crazier.

Exactly! Way back in high school there was a new girl that came and a couple friends and I decided to befriend her even though our group was pretty tight knit. Long story short, we spend a ton of effort trying to include her, but every time she would come up with an excuse not to join us or leave because she was bored. A couple weeks later we are called to the principle's office because asking us why we are bullying her. Turns out she told her mom that we refused to be friends with her and shunned her for not wearing the same clothes as us...... what? Something like us wearing nice clothes (Abercrombie back in the day) and we judged people for not wearing the same. She was the one wearing Abercrombie, but said she only bought it to fit in with us.

Idk i guess I'm reminded of mac in sunny. Are you actually telling me you dont wear condoms when you have sex with strangers? "Why would i wear a condom if they are a stranger?"

As she at least hot? The Italian/Lebanese combo sounds intriguing...

Edit: fucking auto-correct

Oh, those fancy shmancy ones that have studs or ribs on them ya mean?

You call 'em "Love-making" condoms?

I like it. I guess you gotta love someone if you want them to have pleasure too. Makes sense I s'pose.


Oh good. Hopefully he used that moment as reason #1 as to wear protection. Or at least on his top 10 list for why

It's Rivy now and yes, space aids

A bottle of Jack would be awarded to the roommate that could go the longest without speaking to Angelica.

I've met my fair share of crazy, annoying people, but this is not the right way to handle them.

Wait are you Rivy? You friend is Rivy right. Ha space aids.


i enjoyed reading this lol kept me on ur toes

Get off his toes


She knew him for 1 day. How many other guys has she known for 1 day.

Even if you know for a fact 100% she has birth control wear it anyways. Pills don't protect against STDs

This story made me nostalgic for college life. A BUNCH of lines in this made me laugh out loud, and the whole story was well delivered. Very funny read man well done.

and then burned the station down!

Yeah antibiotics and birth control don't mix. Found that out the hard way and now have a 16 month old to show for it.

Oh snap. I'm sorry for you

wow lol

I couldn't even date one girl with the same name as my ex

My underage drinking ticket at college was $270.

He's fine and in a happy relationship with someone he loves. Great ending for Dan!

Fair enough, hope they got away unscathed :P

And whoever punished them for this like jesus is this how bad this whole fucking snowflake issue has gotten?

will you make a post on that too?

We share the account

Thank Dan!

Dan would say the same thing

You all sound like terrible people.

Just wait ;)

I've had the unpleasure of meeting many

You Are good

Fuck, that's my wife's name


There's always that one crazy person you meet in college.

I feel like you definitely were (also) the assholes there. Just because Angelica isn't a great person doesn't give you the right to bully her.

I also have to imagine that your description of her is maybe possibly probably slightly biased.

In consequence, we were written up, paid a fine, had to go to alcohol safety classes, and conduct hearings which made us miss important class time

No, you faced these consequences because you failed to clean your room of things you could be written up for before a search you were warned was coming. Idiots.


It was wild