When Dates Go To $#!#
When it comes to matters of the heart, things tend to get a little messy. In honor of Valentine’s Day, we collected some of the best stories about the worst dates. And if you’re feeling lonely this Valentine’s Day, just be glad that you’re not one of these five people.
The Silent Treatment
When Carson’s friend bummed a cigarette off of a girl standing outside of Ginza, Carson* got to talking to the girl’s friend, Emily — and he was surprised at how well the conversation was going.
After all, 2 in the morning outside of a nightclub doesn’t often make for the best setting when it comes to scintillating conversation, but there they were, discussing their jobs — he’s a physical therapist and she’s an elementary school teacher — and their family backgrounds.
It was a good enough chat for Carson to want to text her the very next day.
“I was like, ‘I enjoyed meeting you, you are really cool, let’s hang out again soon,'” recalls Carson, 28.
So that’s why it was a surprise when, a few days later, the two went out for dinner and the conversation was not exactly flowing. In fact, there was barely a conversation at all.
As they entered the restaurant, Carson asked Emily a fun get-to-know-you question: If she could only eat one food for the rest of her life, what would it be? She responded, but then didn’t ask him for his answer. The trend continued throughout the night. He asked her what had inspired her to teach elementary school — she told him, and then nothing. Question after question, and nothing in return.
“It was just a lot of yes and no, or close-ended answers,” he says. “If I didn’t give an effort to it, I think we would have been silent the entire night, that’s how bad it was.”
Trapped in the confines of a sit-down dinner, though, Carson had nowhere to go. It went on for nearly two hours.
“There were a lot of awkward silences. Super awkward. I was like, I am running out of questions! Please ask me a question!”
After dinner, they headed to Beerworks to meet up with a group of Emily’s friends. He thought maybe things would be better there. Instead, he ended up talking to her friends more than her.
Carson’s not sure why the night took such a bad turn. But he speculates that perhaps it had something to do with the fact that he’s a traveling physical therapist who’s only on assignment in Hawaii through June — a detail she hadn’t been aware of initially — or maybe she was just really shy.
Whatever it was, he’ll probably never find out. After they parted ways that night, he hasn’t heard from her since.
“That was that,” he says. “I didn’t bother texting her, and she hasn’t texted me.”
Bethany, a 25-year-old school administrator, has been online dating for about a year, and as she aptly puts it, the messages you get on dating apps “can be miniature horror stories in themselves.”
So when Dave messaged her last summer, it seemed like a nice change of pace. Notably, he didn’t use the type of cheesy pick-up lines or lewd come-ons that tend to populate the apps.
“He seemed really sweet and nice,” recalls Bethany.
So even though there were things about him that normally would have given Bethany pause — he was eight years older and in the military (“I’m not really interested in the whole after three years they move away type of deal,” she says) — she decided to accept his offer to go on a Pokémon Go walking date.
“I figured it would be OK to give him a chance,” she says. “There is no harm in a first date.”
They spent the day walking around Kakaako, chatting about all kinds of things — their families, their childhood, their interests.
They made plans to see each other again soon, and during their second date, he asked her to come back to his place — just to meet his dogs, which was one of their shared interests. But when they got there, he suddenly became fixated on the trash in his kitchen … and the idea that Bethany should be the one to take it out.
“All of a sudden, he asks me, ‘You know when you are at a friend’s house and you notice that their trash is full, don’t you take it out for them?'” Bethany recalls.
“I realized he was actually expecting me to take the trash bag in his kitchen, tie it up, walk it out to the dumpster, and put a new trash bag in the trash can,” Bethany says. “He was expecting me to do that, and it was my first day of being at his house. And I was just shocked.”
Suggesting that a house guest take out the trash — let alone on the second date — felt rude enough, but things got worse when he became angry that Bethany still wasn’t offering.
“He was like, ‘When I am at a friend’s house, I would do that for them. I don’t understand why you’re not doing that for me.’
“This is also when I found out that he smokes because he had to walk outside and smoke because he was so frustrated that I didn’t take his trash out.”
When he returned, he sat down and turned on the TV, not saying a word. The silence lasted for a while.
Bethany felt awkward, but she stayed, clinging to the thought that their interactions up until that point had been so positive — and she started to wonder if maybe she should take out his trash. Was that a normal thing to do? Was she doing something wrong?
Ultimately, though, she realized that the whole thing was a big red flag: If he was this irrationally angry about such a small thing, how would he react when a real problem came up?
When Bethany left that day, that was the last time she ever intended to have contact with him. But soon after, he added her on Snapchat and Face-book, and messaged her suggesting that they be friends with benefits.
She’s since blocked him.
Sitting across from Tiffany at Cheesecake Factory, 22-year-old Brian remembers the point at which things started to seem a little off: It was toward the end of the meal, and all of a sudden, the conversation got a little bit heavy.
Brian had met Tiffany just a few days prior while dancing at a bar in Waikiki, and this was their first date. The early part of the meal was fine, but then Tiffany started detailing her litany of family troubles. It wasn’t your typical first-date fodder.
Maybe the conversation had upset her. But whatever it was, Brian, who’s in the military, was not prepared for what happened next.
After leaving the restaurant, they decided to go for a walk on the beach. But first, Tiffany wanted to stop into 7-Eleven to get an after-dinner drink. She emerged with a fifth of Jack Daniel’s — and then proceeded to chug the entire thing.
“She chugged it as soon as we left the store,” Brian recalls.
They strolled down to the beach, and by the time they stopped at a pavilion near the water, Tiffany was belligerent.
“She started talking really loud about people when they were standing right there. Then she was yelling at people.”
She seemed to unleash on any passerby.
“She started yelling at random people that they were fat, and then she was yelling at people to watch their kid, and he wasn’t doing anything.
“When people told her to be quiet, she said, ‘It’s a free country, I can do what I want.'”
After his own failed attempts to get her to calm down, Brian called a cab and took her home, where he dropped her off with her roommate.
The next day, though, Tiffany texted Brian, saying what a great time she’d had that night.
“I asked her, ‘I just got a new number, do I know you?’ And she never replied.”
Leilani had the perfect plan to celebrate her 23rd birthday: She and her girlfriend of two years were going on a surfing trip for the weekend with all of their friends.
But things quickly went awry. Not long after they all hunkered down at the campsite, Leilani’s girlfriend, Stephanie, began arguing with her about why Leilani had barred her co-worker — a man whom Stephanie had cheated with just six months earlier — from joining them that weekend.
“I guess in her head, it was enough time for me to be able to be OK with it,” Leilani recalls. “But it was my birthday camping trip, and I didn’t want that at my celebration.”
Leilani told her as much, but Stephanie persisted, insisting that Leilani should be over it by now.
“I was surprised that she was arguing with me about it at that time,” Leilani says. “I said this is my birthday, and if you want to invite him, you can go surf with him elsewhere.
“And then she said if I am not OK with who she hangs out with, then she doesn’t want to be with me and that it is done.”
But despite that she just broke up with the birthday girl, Stephanie decided to stay and camp for the rest of the weekend.
“It was just really awkward,” says Leilani. “There was a definite split — my ex and her friends on that side, and then me and my friends on the other.
“I don’t remember too much after that — there was a lot of alcohol involved in the rest of the trip.”
While Leilani was upset, this type of thing wasn’t exactly unexpected — by then, she and Stephanie had broken up and gotten back together more times than she could count. So she kind of shrugged it off — that is, until the next morning. As Leilani came out of her tent for an early-morning surf, she saw her ex — exiting another girl’s tent.
“I ended up in a tent alone, left to cuddle a bottle of Crown, while my now-ex went to cuddle up with one of her new friends. For the next two days and one night, I celebrated my birthday with swollen Asian eyes from crying and a bottle of any alcohol within my clench.”
In the months before starting college, Clarice and Rick connected quickly over their similar music tastes, and when they started school, they happened to have a bunch of classes together.
Clarice suspected that Rick might like her, but she was never romantically interested. He was handsome, she admits, and he was always doing super sweet gestures for her — like once, he came back from a trip with a set of bootleg albums by some of her favorite artists. But there was just that certain spark missing.
In the middle of sophomore year, though, they were both single and Clarice figured she’d try and see if there was something beyond friendship there.
“I was like, eh, whatever, you never know, maybe I should give it a try,” Clarice recalls thinking. “He had been so persistent, maybe I was missing something.”
So, one night, Clarice went to his house, and talking and listening to music soon turned into, well, a little more than talking. He was on top of her, they were kissing, and suddenly, he pulled back and lifted himself up to look into her eyes … and then deliberately spit on her, right into her mouth.
“I didn’t understand, I was like what the f*&^!,” Clarice says.
She had heard of other fetishes, but spitting in someone’s mouth? Was that a thing?
“It was just gross. I was in disbelief. I cringe every time I think about it.”
Clarice wiped her mouth and immediately told him that she wasn’t feeling well and wanted to go home. He offered to take her downstairs and pay for her cab, but she brushed him off. She lived about 30 minutes from his house — meaning a cab ride could run her about $60 — but she didn’t care.
“I could not have gotten out of there faster,” she says.
Afterward, Rick tried to talk to her — they still had to see each other in class, after all.
“He would text me, like, ‘Hey, let’s hang out, I want to take you out,'” Clarice says. “I was just not having it.”
But he never did ask her what was wrong, so Clarice suspects that he knew she was disgusted.
“I think he wanted another chance, but I just could not have a date with this guy who spit in my mouth.”