The 8 Most Awkward Coffee Dates Baristas Have Witnessed

9 min readNov 29, 2020

PHOTOGRAPHED BY NICOLAS BLOISE.

Once upon a time, a friend told me that no one really takes people out on coffee dates. But I (ever the least fun person at a party) proved her wrong. Because I almost exclusively ask first dates to meet me at a coffee shop. Something about the atmosphere just makes me feel relaxed. Somehow, chatting over a latte or a cup of tea on Saturday afternoon feels way less loaded than sipping on a glass of wine at 9 p.m. on Friday night.

I can’t pretend that most of my coffee dates weren’t awkward, as first dates tend to be. But, they did and do still happen. I’ve actually witnessed several other people on awkward coffee dates just by popping into Starbucks for a black tea. So, in the spirit of continuing to prove my friend wrong, I asked baristas to spill the beans (pun intended) about the most awkward coffee dates they’ve witnessed. Ahead, eight baristas spin some of the saddest and most cringe-worthy tales you’ll ever read.

Rebecca, 24

“This isn’t awkward! Just sad. I saw a girl sit down and wait for at least two hours for someone to show up. She sat in my section, and ordered coffee after coffee, just waiting. Eventually, I stopped by to see if she needed anything else. And she just started crying. She said, ‘I guess he’s not coming after all.’ I gave her a cookie on the house, but she didn’t eat it.”

Hanna, 17

“This guy waited three hours for his date to show up, and once she finally did show up she was very rude to him and kept getting mad that he wasn’t talking much. She proceeds to leave after about five minutes there. He comes up and says to us, ‘Well that was the most awkward first date ever.’”

Molly, 23

“I was working front register when a girl walked in, clearly dressed up for a date, and sat in the cafe immediately. A few moments later, a man I’d gone to high school with who was a complete jerk walked in and sat with her. They’d obviously never met before.

“I could hear him talking about how much of a player he was back then, and how he’d turned his life around to respect women. The girl’s face went from horrified to bored while he said, ‘Oh I love women so much! Women are how this society gets going. Men wouldn’t be anywhere without their wives to have children!’ I’ve never seen someone book it from a date as fast as she did. He didn’t even look concerned, just stood up, ordered a black coffee from me, and went on his way.”

Keely, 20

“Oh god, so this is what happened: He went up and ordered this giant-ass drink, which came to like $7 and change. She ordered a small latte. When I read the total, she looked at him and he wouldn’t look up from his phone. She pulled out her debit card, looked at me, and started laughing. We made their drinks, she took his giant one and left.”

Jordan, 23

“One time, a younger regular (guy, mid-20s, athletic and conventionally attractive) came into my café all dressed up, which I complimented him on when he ordered (he usually stopped in for iced tea and a chat after hitting the gym, still dripping sweat), and he thanked me and told me he was going on a Tinder date with the ‘girl of his dreams’ that he had been chatting with for the past two months.

“After an hour, I checked in on him and he told me his date was running late and asked me for a phone charger. Being in a ‘Tinder success story’ relationship myself, I happily let him borrow my charger and got back to work, knowing all too well how he was feeling. Two more hours go by, and it’s time to close up. It’s been three hours since his date was supposed to arrive, and I had developed a sinking feeling he got ghosted since our prior conversation. I think he knew, too, because his entire demeanour had changed from nervous to utter despair in the time since he sat down.

“I finished cleaning out our pastry display and offered him a croissant and a large cup of coffee for free before informing him he had to go since it was time to close up. He looked at me with the biggest, saddest eyes (I could tell he was barely holding back tears at this point) and whispered, ‘Oh… okay… thanks,’ and walked out. It was the worst I’d ever felt telling someone they had to leave, and we never spoke about that night again. I heard he’s in a very happy relationship now, though. So it looks like it all worked out in the end.”

Kat, 26

“I once saw a girl and guy make out outside for a solid 20 minutes, then come into the store. They paid for their drinks separately, sat down, and talked for what was like a half hour more. Apparently, the guy was breaking up with the girl, judging from the fact that by the end of it she was crying and they left separately.”

Alison, 22

“A former male barista that we considered a cool surfer dude and a blonde girl were sitting in the café, and you could tell from the moment they walked in that date was a nope. The girl looked uncomfortable, as he was staring at her like a lion planning to chase a baby gazelle, barely blinking. And she looked at us as if communicating with her eyes that she couldn’t wait to leave.

“The date lasted 30 minutes, and my coworkers and I kept an eye on the girl to ensure she was okay. Then he said to her, ‘Are we going over to your place or…’ She replied as fast as she possibly could, ‘NO. I have to go.’ He proceeded to attempt several times to guilt-trip her as if she owed him time in a sexual manner. The more he talked and talked about how much he wanted to have sex with her, the more the girl, my coworkers, and every woman in the cafe felt disgusting and made signals for the girl to realise that it was definitely time to go. As she stood to leave, he decided to follow her out, and both got into their own cars. Neither one of them left the parking lot for 15 minutes, until he decided to accept that he failed and drove away. Minutes later, she went home.

“After that, my shift on duty came in and said, ‘Oh I missed my crushtumer, isn’t he cute?’ And all of us looked at each other and answered, ‘Hell no.’”

Sarah, 18

“A teen came in to meet up with a girl from school. Girl never showed up and was crying in the bathroom for a good 30 minutes. She got a Frappuccino and left. About 20 minutes later, a girl came in asking for the teen who had just left.”