"If You Hadn't Boned Our Son's Girlfriend And Gotten Her Pregnant, We Could Afford To Eat Somewhere Nicer Than Olive Garden": 17 On The Most Awkward Dates Servers Have Witnessed On The Clock

"If You Hadn't Boned Our Son's Girlfriend And Gotten Her Pregnant, We Could Afford To Eat Somewhere Nicer Than Olive Garden": 17 On The Most Awkward Dates Servers Have Witnessed On The Clock

As we all know, dating can get exacerbating. So, when I came across this Reddit thread where people who've worked in the food service industry were sharing the most awkward dates they've ever witnessed, I just had to share. So, sit back, sip some tea, and prepare to be entertained...

Elderly woman with glasses smiling, holding a teacup, seated indoors with books and a plant nearby
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1."A couple came into the restaurant dressed very goth. I wasn't their server but I was running the cash register just a few feet away. They proclaimed to everyone that they were energy vampires but not to fear them because they wouldn't hurt us. They said they didn't need our food for sustenance, but enjoyed the taste. After ordering the meal, they politely asked the waitress if she would stick around for a second so they could feed off of her aura and have enough energy for the night. The waitress said yes... 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 tipped well for her delicious energy."

Two people dressed in gothic attire, embracing and showing vampire fangs
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2."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, asshole.'"

Smartphone displaying Olive Garden logo with a blurred restaurant sign in the background

3."I witnessed a first date, I would estimate they were college age. They’re eating and the girl says, 'I’m having a really nice time but my friend just texted me and asked me if I wanted to hang out, and I said yes, so I actually have to go.'"

Person looking at a smartphone screen with text messages, indicative of modern communication in relationships
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4."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. I ended up boxing up their dinner. The guy paid, but I do not envy that ride home."

Two people holding hands over a table with wedding rings and documents, suggesting partnership or marriage
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5."I had a couple come in one night and everything seemed to be going fine. We just hired a new server who was training. 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 couple's table and all I hear from the new server is, 'YOU FUCKING BITCH 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."

Woman splashing water from glass onto man's face at a table, showing a heated argument
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6."Husband and wife fight. Wife cried. Husband got up and threw a pizza slice at her face."

Pepperoni pizza with slices removed, on a cardboard background
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7."When I was waitressing in college, 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."

Man proposing to a woman with a ring, both seated with champagne glasses on table. Woman is emotionally covering her face
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8."A girl brought two tinder dates and played them off each other game show style. They seemed to be unaware this was what would happen. Splitting the bill was hilarious."

Two people's hands on table with wedding rings and document, suggestive of marriage or partnership


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9."This couple sat down and, from the girl's body language, you could tell she was into him. As the date progressed she closed off, sat pretty much sideways, and played on her phone. The body language shift occurred over maybe one and a half hours. He didn't stop talking the entire time. She did give some nods and 'uh huhs' in response — she even perked up a few times to contribute...but his monologue never stopped."

Woman resting head on desk next to computer and foam cups, appearing exhausted or asleep


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10."Not a waiter, but I was working as a supervisor in a restaurant. There was a couple that came to lunch every day and, every day, they went to the bathroom together for like 20 to 30 minutes, so we all assumed they were having sex. 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."

Two people sitting across a table with glasses of water, appearing to have a conversation
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11."I've told this one here before. I worked in a resort hotel, high end, I waited tables in the fine dining restaurant. It was pretty common for people to propose there, so much so that I had a system for the whole thing. One guy came in and wanted to do the ring in the champagne thing, and I talked him into doing a dessert alternative that doesn't result in a sticky ring and champagne on the floor. Anyway, long story short. I bring the ring, she says "Dammit, I've told you before I'm not marrying you." He flips, she's super calm about it and basically treats him like a child having a tantrum, which to his credit he was not screaming or anything, just very upset. He left, she ate the fucking dessert, eventually he came back and paid and they left together. Super awkward."

A woman looks annoyed while talking to a man outside a cafe, hand raised in a questioning gesture
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12."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 asked me questions like, 'I’ve heard the owner of that place is crazy, did you know her?' Turns out, she was purposely trash-talking 'not-Mark's' wife."

A man and a woman flirt at a bar while another person watches
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13."There was a couple at my work having drinks, girl went to the toilet, came back, and admitted that she’d been sleeping with the guy's brother. Apparently, glasses were thrown across the room and they both got kicked out."

Man gesturing animatedly during a discussion with a woman at a restaurant table
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14."A guy proposed to his girlfriend at Olive Garden. When he got down on one knee and opened the box, she shook her head and 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 much it cost, the different aspects of it, etc. Finally, the girl just said, 'No.' The guy sat back down and they tried to finish their dinner."

Woman with blue hair looking directly at the camera with a neutral expression
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15."There was a couple sitting at the bar together, it seemed like it was a 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 left."

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16."An ex of mine came in to eat where I was working with his girlfriend, and she left crying halfway through. Apparently, he brought up that we dated, and he kept looking at me, which somehow caused that whole scene."

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17."This wasn’t so much as awkward but just unusual: Served a young couple at a high end Italian restaurant that came in wearing matching outfits. I asked them what the occasion was. They were celebrating their 3 month anniversary. I’m so glad they found each other."

Two people in matching festive sweaters holding wine glasses, smiling, with a winter-themed backdrop
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Have you ever witnessed or been on a really terrible date that tops these?! We wanna hear your horror story in the comments!