Waiters Share The Most Awkward Dates They Have Ever Witnessed

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Things can go many ways when you’re dating; you could end up meeting the man or woman of your dreams, or it could go up in flames so bad that not even your local fire department can save it. More often than not, we go through some pretty bad dates before we meet someone we actually vibe with and it’s those horror stories that really entertain.

But can you imagine not actually being on a bad date, but seeing it play out first hand, while you’re at work? The people in this article have witnessed it all, and then some. These are the most awkward dates that waiters have witnessed while working.

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42. The Most Heartbreaking Proposal Ever!

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When I was a waitress, I witnessed the single most embarrassing thing to happen to a person. Right in the middle of their dinner (and in the middle of our Friday night dinner rush), this poor guy stood up, tapped his wine glass to get EVERYONE’S attention, and then proceeded to tell EVERYONE what a fantastic person his girlfriend was.

The whole time this is happening, she was just sitting there with the most bored look on her face. Then the poor guy pulled out a ring, got on one knee and asked her to marry him. She gave him the most disgusted look imaginable and said, “This is the ring you expect me to say yes to? Could you be any cheaper?”. She got up and walked out, leaving the poor guy just kneeling there. I didn’t charge him for the meal.

41. Family Affair

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I waited tables at Olive Garden 10 years ago. A guy and his wife sat down at a table and immediately started arguing. Something about his affair and how a baby from it was costing them money. Finally, it culminated as I was bringing out their salad.

As I walked away, I heard the wife say, “well, maybe if you hadn’t boned our son’s girlfriend and gotten her pregnant, we could afford to eat somewhere nicer than Olive Garden. Oh look, the highlight of my meals, UNLIMITED. BAGGED. SALAD. Maybe you could save up and we can go to Joe’s Crab Shack for our anniversary, jerk.”

 

40. Dine and Dashing

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There was a couple sitting at the bar together; it seemed like it was their first date. I was in the back rolling silverware and, after about 30 minutes of them sitting together, the dude came running into the back and asked, “There’s an exit back here, right?”

He then proceeded to bolt out of the back door. We were all flummoxed. The girl sat at the bar alone for AT LEAST another 45 minutes before she realized that the guy isn’t coming back anymore. She then PAID for their meal and left.

 

39. Serving Surprise

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I was working at a wine bar when a married couple sat down on a pretty slow night. I went over the specials and they ordered. Once appetizers came out, the man thought it would be a good idea to serve his wife divorce papers.

I did my best to avoid that side of the bar, but I did bring out tissues for the wife, who was breaking down. It was a complete surprise to her. I ended up boxing up their dinner. The guy paid, but I do not envy that ride home.

 

38.  At Least She Paid before She Left

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I was serving one night and was like 19 at the time. I was very awkward myself, and there were two ladies in their late 30s. One of the women came up to me and explained that she wanted to pay and leave without the other woman knowing. And she did. She even said the date wasn’t good for her.

But like… her date sat there for a long time waiting for her to come back and eventually I went and awkwardly told her “Hey…so your meal is paid for and you can leave if you want.” She seemed surprised, but she didn’t take it too terribly.

 

37. The Emergency Exit

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A gorgeous blonde woman in her late 20s was sitting with a very well-manicured looking man in his mid-40s. He’s dressed like he just left a high-dollar law firm. He was polite, talkative, and super into her, but you could tell that she wasn’t reciprocating the feelings. When the guy went to the bathroom, she quickly picked up her phone, frantically called someone, and begged for a pickup ASAP.

The gist of the call was the guy was her mother’s coworker and her mother had set the date up, and our girl really wasn’t feeling it. About 15 minutes later, a guy around her age came in, threw some cash on the table and excused them. She cited some vague emergency and was escorted out. The older guy continues drinking, trying to get the waitress’ number, fails, pays in exact change without tipping, and leaves.

 

36. My Love Don’t Cost A Thing

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A guy proposed to his girlfriend at Olive Garden. When he got down on one knee and opened the box, she was shaking her head and then just stared silently. It must’ve been a whole 30 seconds of pure silence, but it felt like an eternity.

Then, the guy proceeded to describe the ring, how expensive it cost, the different aspects of it, etc. Finally, the girl just went, “Noooo.” The guy sat back down and they tried to finish their dinner like nothing happened. I caught eyes with our server and he made the most perfect “holy hell that was bad” face. Geez, that was awkward.

 

35. You ain’t Very Talkative, Uh Huh?

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A couple sat down and from the girl’s body language, you could tell she was into him. However, as the date progressed, she closed off, sat pretty much sideways, and was playing on her phone.

Her body language shift occurred over an hour and a half because he didn’t stop talking the entire time. She gave some nods and “uh huhs” in response and even perked up a few times to try and contribute to the conversation, but his monologue never stopped.

 

34. Why Waste Time Dating, Eh?

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I waited tables in this fine-dining restaurant. It was pretty common for people to propose there, so much so that we had a system for the whole thing. One guy came in and wanted to do the ring in the champagne, but I talked him into doing a dessert alternative that doesn’t result in a sticky ring and champagne on the floor.

Anyway, I brought out the ring and the woman said, “Dammit, I’ve told you before I’m not marrying you!” He flipped, but she stayed super calm about it. He left, she ate the dessert, and he eventually came back, paid, and they left together.

 

33. My Boss’ Husband’s Mistress

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I was bartending a day shift at an upscale Italian place. This couple came in, started drinking, and were VERY flirty with each other. I wasn’t quite sure why, but the man seemed familiar. Midway through their lunch, the woman used his name and it dawned on me that the man was the husband of my previous boss.

I asked if he was “Mark” from “that restaurant on the way to the beach?” He said that he was NOT, but the woman he was with insisted on making it awkward and peppered me with questions like, “I’ve heard the owner of that place is crazy, did you know her?”. It turns out, she was purposely trash-talking ‘Mark’s’ wife.

 

32. That’s Why It’s Better to Ask First

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Some older couples have a habit where the elderly gentleman will order on behalf of his wife. I guess it might have been cute and romantic once, but it doesn’t work with younger couples. Basically, I was serving a younger couple (early 20s) who seemed pretty early in their relationship. They were ordering drinks and the guy ordered the girl’s drink for her.

Far from being dazzled by him knowing what she wanted, she said: “Well, I’d actually like a latte, not a coke…but fine, whatever, if I don’t get a say.” He responded angrily with, “Oh sorry, have what you want then!” She got her latte and he glared at me.

 

31. Does Ice Cream Make You Talkative?

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I worked at an ice cream parlor — it was kinda old-timey, with not much seating. Anyway, a guy came in with a girl; they paid for their own cones and took up two of the seven stools. The guy was talking and, at first, the girl was laughing and into it.

Cut to two hours later, the dude is still talking. The girl looked like she wanted to cry or punch him in the face. The guy never asked her a question and never let her say more than a few words before he’d stomp out her ‘rude interruptions.’ Finally, I said, “Hey guys, we close soon. I hope you have a nice day, but we need to mop.” I watched them walk down the street and he was STILL TALKING. Like, get a room with yourself, guy. You’re obviously the man of your dreams.

 

30. She’s Not Loving it!

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I worked at McDonald’s, and a couple came in. The woman sat down and the man tried to order. There was lots of ‘Uhmm’-ing and ‘Ahhh’-ing over what he wanted to buy, then he ordered two meals, we gave them to him, and he went to sit down.

What followed was a 10-minute shouting match about how he wouldn’t take the woman on a “proper date” and how messed up a McDonald’s date was. I guess he ordered the wrong thing? Or maybe one meal wasn’t enough for her?

 

29. Divorce Settlement

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I served a couple one time who had met up to discuss the terms of their divorce at the fancy-ish restaurant I worked at the time. They came before the dinner rush, so they were pretty much my only table, and every time I’d check in on them the wife was extremely angry/tearful and they were bickering about holiday schedules for their daughter/timeshares, etc.

It wasn’t the end of the world, but it was extremely awkward to butt-in to change out their forks or refill drinks while they were so emotionally-charged. As awkward as I felt in that moment, it was really nothing compared to what the couple was going through.

 

28. She’s in love…But with His Friend

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A couple comes into our restaurant for dinner and the guy then secretly tells me he has a ring and wants to propose to her and wants it to be all special. I was to wait until a specific time and come and ask if the table “needed anything else” and then he would say “I do…I need her…” And then get down on his knee, etc.

I thought it was cheesy, and since I wanted to be a part of something like that, I helped the guy. I get to the table and ask the question, he then pops the question and she burst into tears. But not good happy tears. She then blurts out that she wants to break up and that she was in love with another guy, apparently a friend of his. I just slowly backed away from the table as his entire world came crashing down on him.

 

27. Energy Vampires

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A couple came into the restaurant dressed very goth-like. They proclaimed to everyone that they were energy vampires, but we shouldn’t fear them because they won’t hurt us. They said they didn’t need our food for sustenance, but enjoyed the taste.

After ordering the meal, they then politely asked the waitress if she would stick around for a second so they could feed off her aura so they could have enough energy for the night. The waitress said OK and gave me a side glance over her shoulder that I knew meant “I better get a good tip for this.” The couple clasped each other’s hands, closed their eyes, and made sucking sounds for a solid minute before leaning back in the seats and sighing as if they had just had a turkey dinner. The waitress was indeed tipped well for her delicious energy.

 

26. So She Is Married

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It was a Sunday morning shift at the restaurant in town and it’s always so dead. But I’d bring homework, so it was mostly OK. Every other week, this couple would come in and order G&Ts and nachos and sit for hours talking about how attracted they were to each other, their bed life, and would joke about sneaking around and whatnot.

One day, I walked into the dining room from the kitchen and saw the lady had already been seated in a booth facing me. Her dude’s bald head was across from her, facing away from me. I approached the table, about to ask the love birds if they wanted their usual, when the dude turned around; it was a different person. The lady looked at me sheepishly as he mentioned to me it was his “wife’s” birthday and they had never been to my restaurant before.

 

25. The Club Dancer

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I was in a hotel breakfast restaurant where a drunk conference attendee had been coming to breakfast solo and drunk for about three days. He came down with a beautiful woman on his arm that I had seen him bring in the night before.

He then greeted me, in front of a crowd of guests with, “Hey! Have you met my date? She’s a club dancer! But isn’t she so pretty? I’m trying to convince her she doesn’t need to be a dancer!” She ate in miserable silence while he told the entire wait staff over and over about his beautiful hooker date. I gave her a free mimosa.

 

24. I Got My Eye On My Date

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I was at an Irish pub, and it was a couple’s first date. They are at an outside table getting to know each other having a pleasant conversation which seems to be going well. Then a drunk girl entered and she’s totally plastered. She takes a liking to the guy and decides to go over and join their date. She sits at the table slurring “Heeeey you’re cute!” proceeds to climb into his lap and try to grind on him.

Everyone’s watching this slow motion train wreck. He removes her and gently sets her down and continues paying attention to his date. She won’t give up, so he pulls the best move ever: he buys her a shot, she does it and promptly passes out on the table. They continue their date completely ignoring the drunk brat sleeping right next to them. I hope they worked out; I’d love to hear them tell their ‘how I met your mother’ story.

23. Together Or Separate?

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There was a couple, apparently on a first date. As I would come by with drinks and to take their order, etc., I noticed that they were hardly talking or looking at each other, at all; the girl was clearly not into it.

Finally, when they were finished with their meal, I asked if the ticket would be together or separate. The guy said “together,” and the girl said “separate” practically at the same time. It seems like they each had a different experience on this date. It was very cringy to hear.

 

22. The Song Of Confession

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I work at a dinner theater, and we usually do proposals where we set up a ‘random draw’ where the ‘winner’ comes up on the stage to win their prize, and are then surprised by their partner who proposes. It’s usually sweet and makes everybody in the room all fuzzy and warm. One guy requested to perform a song. We’re pretty easy going at this job, so we agree to let him do it.

We do the fake draw, the woman comes up on stage in front of a room of 400 people, and the music starts to play. Apparently, the guy was a little nervous and compensated by having a few drinks. So what follows is a slurred performance of a song he wrote, that seemed to focus on how he was sorry for cheating on this woman with her sister and at the end of it, he gets down on one knee and proposes. Usually, this gets a round of applause, encouraging the person to say yes; but not after that train-wreck of a performance. The poor woman was just holding her face the entire time and starts shaking her head and says “No, what’s wrong with you?” She storms off and leaves him and our stage manager on stage to a bunch of murmuring from the audience. The only thing our stage manager can think of to say on the mic is “Well, that’s that.” The guy ended up staying for the rest of the show and had many more drinks.

 

21. Proposal Went Bad

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A couple came in and the guy had pre-arranged with us to present an engagement ring with the chocolate course with melted chocolate on the plate spelling “Will you marry me?”, accompanied by roses and other embellishments on the plate. Apparently, the entire meal she was explaining to him how bad he was at being in a relationship; that he was too needy, too emotional, somehow also didn’t spend enough time with her and wasn’t connecting with her. It was basically an hour-long breakup speech.

We come around the corner with candles lit and the chocolate fondue and the engagement ring on the plate. The table next to them did everything they could to wave us off and I was holding a camera to capture the magical moment…which never came. He tried to get his prepared remarks out, but it was so bad we eventually left the dessert at the table and tried to act like nothing had happened. She left before the check came.

 

20. Pay Bill Fight

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I worked as a cashier at a self-service cafe. The cashier counter is in between two big glass display racks displaying desserts, etc. for sale on either side. I was taking their orders, mind you there were more customers behind them, when they started fighting about who was going to get the bill.

They both started shoving cash at me past the counter when a 20 dollar bill belonging to the girl fell in between the counter and the display rack. It was a really tight spot and neither of us could reach. The display rack is also really heavy and big. She then proceeded to ask me to get a knife and many other random things to get her 20 dollar note. The worst part was the other customers were clearly impatient.

 

19. Silent Couple Fight

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I served a deaf couple having a fight. They went from both of them signing furiously to her crying and signaling to me for a stack of napkins for, I assumed, her tears. She whips out a pen and starts writing paragraph angrily.

It was awkward because I kept having to come back to the table since they ordered multiple courses and he was just eating and signing while she was hunched over the table writing away while crying. When they finally left, they tipped me pretty well though so I guess it wasn’t too bad.

 

18. Caught In The Act

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I had a couple come in one night and everything seemed to be going fine. We just hired a new server who was training and I asked her if she had any questions. She was still nervous about greeting tables so I told her she could shadow me and watch what I do.

We go over to the couples table and all I hear from the new server is “You jerk! I knew you were cheating on me!” Turns out the guy was her boyfriend on a date with his side chick and he didn’t know she just got a job there. She didn’t get fired for what she said.

 

17. Date-saster

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A couple comes in right around peak hours; the guy looks annoyed and the girl looks really excited. The girl is trying to talk to this guy and he’s completely ignoring her. He gets a call and talks on the phone for a good 10 minutes, hangs up and starts talking to anyone around him. He’s getting more and more drunk and starts hitting on the female waitresses. The girl he’s on a date with has started crying at this point and once he actually notices, he yells at the bartender because it was obviously the restaurant’s fault for her being upset. She yells at him to stop yelling at the bartender because he’s been such an awful date and he goes off, tells her he didn’t even want to eat here, she should’ve picked a better place, and he isn’t paying for her food and drinks.

The girl is super upset and I tell her there’s a back door she can leave through and I can get her tab from the bartender. I go back out and the guy had already stormed out and refused to pay, leaving his date with a nearly $200 check. She didn’t have the money to pay so a couple of the bar regulars covered it. It made the whole night super awkward and stressful, but it was definitely one of the more memorable experiences of that place.

 

16. Scheduled Dating

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I worked at a fine dining place and there was a couple who would do lunch on weekdays since we were downtown. This one gray-haired bigwig of his company would come in with this young blonde. I was informed right away by the manager that she was the secretary/mistress. They would always sit in one back booth in the bar, together on the same side, laughing and giggling.

On weekends, he would sometimes bring the wife for dinner in the formal dining room, small two-top and very prim and proper. The wife was very particular about the quality of service and they always got the most senior server. It was so awkward.

 

15. Drama Series

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There was a couple that came to lunch everyday, and everyday, they went to the bathroom together for like 20-30 minutes, so we all assumed they were making love. It was inappropriate, but there was nothing we could do.

Then one day, the woman came to the restaurant with another man. That man was her husband, which made for a pretty awkward moment. She started to come to the restaurant with her husband in weekends. And one day, as usual, she came to us with her lover. They were arguing and as I’ve understood, they broke up. She was crying and so on and after that fight, I’ve never seen any of them.

 

14. Strange Couple Date

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A woman in her 40’s and a guy in his late 30’s came in. He was wearing a graphic, gory Happy Tree Friends shirt and she was in a full fur black coat with a mesh shirt underneath, straight up gothic Cruella De Vil. They didn’t speak a word to each other, except when I came to ask how their meal was going; they both started complaining that their wine suddenly tasted of soap even though they’d had the same bottle and glasses since they sat down.

Convenient that they start complaining about a free bottle when they’re reaching the end of their old one. Either way they literally just sat staring at each other in silence the whole meal, then paid, got up, and left. Seriously the strangest date I’d ever seen, and the most on-edge I’d ever felt serving customers.

 

13. The Last Date

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I had a couple come in one time that I waited on; the dude ordered so much food for them. I thought it was a little weird, and then he asked me to give them some time. So after about 20 minutes, I look over and see the girl hasn’t touched her plate at all, while the dude is almost done with everything on the table, and then he asks for the check.

Next thing I know, I see the girl still crying into a napkin and the dude bounced. It turns out that it was their break-up dinner. The dude didn’t pay the tab either; he left her with extra food and an $80 tab.

12. Soakin’ Date

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A couple, luckily not in my section, were clearly on a first date. She ordered a wine and he ordered a beer. The beer was meant to be served in a branded glass but the only clean ones had just come out the dishwasher. The waitress gave him one of these glasses and it must have warm still. She put the glass on the table and poured about half of the very cold beer into it.

This poor guy picked up the glass but the temperature difference made the bottom of the glass sheer off. So his whole glass of beer dropped straight down onto his lap. Obviously, the waitress and manager were all over him trying to help but they couldn’t exactly take his trousers and give him dry ones. So he spent the rest of his date soaked through and stinking of beer. They didn’t order starters or desserts, just had a main and left.

 

11. No Thanks!

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When I was bartending, this guy came into the bar on a ; he. He was an average-looking guy in his late twenties. He sat down and asked for a drink and told me he was nervous because it was his first date in three years and they had met on Tinder. He arrived 20 minutes before her expected arrival to get rid of some of his nerves.

Two hours passed and he waited for her with no text or call explaining she would be late. This woman walks in, walks up to the guy and I’m thinking “Wow! She really came!”. She looks at him and says “Are you Joe?”. The guy replies yes and gets up to properly greet her looking incredibly excited; she says “No thanks…” and just leaves.

 

10. Nightmare Girls

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These two nightmare girls come in with a guy and one kept saying he should sit with the other girl since he had been feeling her up at the mall earlier and he was supposed to be her date. They asked me my opinion and I’m just like yeah that’s not cool.

They come in a month later with two guys in the military and keep bringing up the other guy that was hitting on the wrong one. They also had manhood-shaped lollipops this time and were just sucking on like no one is supposed to question why they are eating them. They were very strange.

9. He’s Hitting On Me

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I had a middle-aged couple who seemed perfectly nice. The man asked me where he could go to smoke. I pointed him in the right direction and then started heading back to the kitchen which was in the same direction. He followed me and told me that the woman with him was his ex-wife. Not knowing how to respond, I said it was nice that they got along so well. He told me she just pretended to seem nice and was actually a terrible person.

I was feeling uncomfortable enough, but then he started to ask my age, if I had a boyfriend, what I was doing later. Thankfully, I could excuse myself to the kitchen. However, serving that table was awkward after that especially since she kept touching and complimenting him.

 

8. Looks Familiar

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I’m a bartender and saw a bad date go down: The girl seemed familiar to me and she kept glancing over at me every now and again. Then the guy started looking over at me too. Even when she was up ordering drinks, she was glancing at me and my co-worker noticed. It turned out she was a friend from years ago who just ghosted our friend group.

The couple had no chemistry at all either; there was little conversation and at a few points, both were on their phones at the same time. Eventually, the guy leaves and the girl’s left there alone for twenty minutes. So she pulls out her laptop and works on Photoshop for a good half hour before leaving.

 

7. Great Rub Awkwardness

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I was a bartender, and helped get two strangers chatting across the bar. They hit it off, talked a lot, clearly into each other. They moved closer, so I turned away and was helping other customers, not paying much notice.

Eventually, I realized that he was now standing behind her with his hands up the back of her shirt, giving her a sensual back rub while her eyes were closed and she’s moaning softly. This was at lunchtime. It went great for them, but was awkward as hell for everyone else in the bar.

 

6. Let’s Not Waste Time

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This awkward, middle-aged guy shows up 45 minutes early for his reservation, so he gets seated anyway since we weren’t busy. He brought a book with him and refused to order anything until his date arrived. His date arrived 15 minutes after the reservation. It’s clearly a blind date from a dating app, so she sits down, refuses to order anything.

I left them alone and for the next 15 minutes, she looks like she’s interrogating the guy. She eventually gets up and leaves. It appeared she was not wasting her time with a full date when she could rush the experience and get on with her life. The guy looked devastated, so we offered to buy him dinner. He declined and left the restaurant in the saddest way possible.

 

5. Hold That Table

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I worked at a higher end place and there was a guy who pulls in the lot in a new high-end BMW. He was a flashy guy; chains on/sunglasses inside type. A girl comes in with him and she’s classy. He walks to a corner table and she walks past him, saying she wants this booth over here. He’s not budging; he says if she wants to eat with him, it’s gonna be at this table.

Well, that doesn’t fly well. They end up leaving, he says to me hold that table, he’ll be back in a few. He drops her off somewhere and comes back 20 minutes later and has steak and lobster for one.

 

4. Orgy Invitation

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I was a manager at a restaurant where my then-girlfriend, now wife, was a server. One day, she came in to the kitchen red in the cheeks and flustered. She said I HAVE to go talk to table 55. I thought it would be a food complaint but when I arrived, the couple sitting there said “oh you must be our server’s boyfriend” which was weird because we normally didn’t talk about our relationship at work, at least to patrons. “We invited our server to a threesome and she said no thanks and that she is in a monogamous relationship, so we thought we would invite you too to make it an orgy.”

I look over at the back of house door to find my girlfriend busting a gut, knowing the awkward situation she just threw me into. It all sort of felt tongue-in-cheek but I could tell they were serious. I told them with a half smile that was not my jam. The man said, “Well, you can hold the camera if you want.” I also politely declined that offer. It turned out both of them were there cheating on their SO’s with each other.

 

3. Why Don’t You Love Me?

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I had a table once where the woman asked the man if he loved her and he said no. She got up crying and ran into the bathroom. This all happened as I’m stood there with a bowl of nachos for them. I asked him if he wanted me to leave them or bring them back when she came back and he said he’d just take them and just sat there casually eating his nachos while she cried in the bathroom.

She didn’t come out for over an hour. She then just sat there sobbing asking him why he didn’t love her and he just seemed so not bothered by the entire situation. It just got more and more painfully awkward; It was Valentine’s Day as well.

 

2. Food Massage…I mean Foot

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So this very nicely-dressed, 40s couple comes in with their teenage children. They tell me his parents will be joining. So everyone sits down and I notice the husband and wife sit where there is an empty chair between them. I thought it was kinda odd, but hey, whatever.

The parents arrive and I get drink orders. I go back to drop off drinks and take orders, and I’ll be damned if he doesn’t have his shoes off and she is massaging his feet. In our restaurant-during lunch rush! So I’m trying not to be grossed out while I’m asking what kind of vegetables everyone wants. It was so gross.

 

1. Order Arguments

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I had this married couple and their two older kids come in once. I gave them the normal spiel and when it came to what they wanted to eat, they argued back and forth about a bunch of things like what the actual price of the food was, how the food affects their bowels and why they shouldn’t eat it. The conversation just got louder and louder about how they couldn’t afford it and how someone was gonna gas up the family car.

All the while, the kids are apologizing for their parents but they get involved too. I kept trying to leave saying “I’ll give you a few more moments” but they kept saying they were ready and wouldn’t let me leave. What the?!

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Ariana Aufiero

Ariana Aufiero

I am an extremely verbal person who excels (and profusely enjoys) writing and/or talking about anything and everything! I love writing... Did I mention that?

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