Food & Drink

The Worst Dates Portland Waiters and Bartenders Have Ever Witnessed


Valentine's Day is a holiday purposely manufactured to make single people feel depressed and lonely. But before you fire up your dating apps in a last-minute attempt to find a date for the gruesome holiday, read these stories of the worst dates bartenders and servers have witnessed. There are worse things than being single on Valentine's Day.

The slap heard 'round the room

"This is back when I was working at the Library. I was having a great shift, I remember; I had sold a shot of The John Walker, which is like $800, and I was feeling good. There was a couple at the communal table, two young men, sipping cocktails, snuggling, sharing a few kisses… Normally I'm pretty anti-PDA, but they were too cute. Eventually, they finished their drinks and closed out. One of them left, but the other went back to the front desk and asked for a different table for two. When his new guest arrived -- another young guy -- he greeted him with a kiss. I was like, 'Oh, shit.'

"They ended up in my section this time, so I greeted them and got their orders. But, when I went back to the bar, I heard a slap from across the room. I brought them their drinks, but the slapper, [who was] the new guest, was bawling with his head in his hands. The other one was sitting rigidly, blank-faced. I presented the whiskeys, as we do at the Library, and poured them. The one who was obviously just dumped for a new boy took both drinks, downed them, and ran out of the bar. I looked to the other one, who was still just sitting there, and offered him his bill." -- Alise Moffat at the Multnomah Whisk{e}y Library

Here comes a (shitty) regular

"A couple was on a date at Aalto during happy hour, and it was busy. I recognized the guy (bright blonde hair) and I thought I recognized them as a couple who always made out at the bar. My suspicions were confirmed when at some point, right in front of my well, they started eating one another's face. I'd had enough. I approached them, asked them to stop, and told them nobody wanted to see that and that I was tired of watching them dry hump week after week. The girl instantly looked pissed and told me she'd never been in before. Turns out, the guy was a cheap fucker and always brought his Tinder dates in. When it went well, he'd make out with them. They were always new girls. I'm happy to report that I never saw him in again and I hope that girl walked the hell away." -- Kate Wood at Aalto Lounge

The OkCupid two-timer

"I used to have a regular that would schedule back-to-back OkCupid dates. He would close out, walk them to their car, and then come back to meet the next one and start a new tab. He always capped off the night with hitting on me until last call.

"Friday was date night for him, and I was always hoping to see it blow up in his face in a rom-com sort of way. Once, one of his dates showed up early while he was still with date No.2. He ended up just never saying anything to her. She was sitting in a corner turned away from the bar so he walked his second date out inconspicuously and then just bailed. It was so sad -- she ordered two drinks waiting for him to show and then dejectedly closed out. I still wish I had said something to her but I just couldn't think of anything to say that would help in the slightest.

"He was such a douche. I always wondered what his motivation was, as he rarely-to-never took a date home and spent countless dollars on them. Maybe it was part of a D.E.N.N.I.S. System." -- Eleysha Nutt at Free House

"Just small talk"

"I was working as a general manager and bartender at Davis Street Tavern, so by the time Saturday would roll in, I would already be exhausted. One such night, this couple walks in and takes a seat at the bar, right in front of where I make drinks. They seem pretty normal to me... at first. At one point, she interrupts the conversation and excuses herself to use the restroom. As soon as she turns the corner, he tells me she's cheating on him. He's been going through her phone and he knows it, but he doesn't know how to confront her, or where to even begin. He tells me he's just so in love with her and is planning on proposing.

"I stand there and nod, awkwardly, while he's unloading this on me. It's all I can do, as I'm mentally drained from him just spitting up all of this. And I'm trapped: I have tickets coming in and he's sitting right in front of my station. She comes back and immediately asks him what we're talking about. He tells her, 'Nothing, just small talk about beer.' She isn't buying it. She goes from being super-friendly to me to immediately thinking I've betrayed her. Things have gotten deeply awkward.

"I leave for a minute to run some food, but I have to quickly return as the damn drink tickets are still flooding in. Mercifully, she eventually demands they leave. He hands me a card to pay, but as I hand it back, she swipes it from him to sign. She doesn't tip, but I don't even care at this point, I just want her to leave me the fuck alone. They leave, with him trailing a few behind her, defeated." -- Adriana Alvarez at Davis Street Tavern

The date 'n' ditch

"I had a couple sit directly in front of my well one night at the Multnomah Whisk{e}y Library. It didn't take long for me to figure out that they had most likely met online and were only a couple dates into having met each other based on their conversation. I remember not being too fond of the guy from the get-go, probably because each time he ordered, he had a condescending tone to make sure I knew that he didn't need my assistance in ordering. This played out to his advantage of getting his ego stroked by his date since she didn't know anything about liquor, thus he was able to educate her and seem real cool. Happens all the time.

"After their first round of cocktails, he chose some whiskey -- slightly lesser-known, but not so great, I might add. I didn't see any indications that the date was going poorly except for maybe that he wasn't as into her and she was into him, but I just chalked that up to nerves. He then gets up after finishing his whiskey to go for a smoke break. He tells her to order another round of the same, which I go ahead and pour since I didn't think he would be too long. I proceed to take care of the rest of my guests at the bar, somewhat forgetting about the couple.  

"I'd like to think she knew that she had nothing to do with the fact that this guy had no class… or balls."

"About 15 minutes later, I notice she starts nervously looking at the front door and then down at her phone, which was full of unanswered texts to him. I casually go over to top off her water and ask how she is doing. She defensively tells me that he had to take a call. Another 30 minutes goes by before I go back to her, hoping that she isn’t still in denial.

"Embarrassed to say it too loud, she tells me she thinks he left. As she's pulling out her wallet to settle up the tab that creep had left her with, I walk around the bar to sit next to her and hopefully offer her a hug. I couldn't help thinking that she might not get one at all tonight. Before I even had a chance to say anything to her, she threw her arms around me and pulled me in. I didn't know this woman at all, but looked her in the eye and told her she was beautiful. She left a little teary-eyed, but I'd like to think she knew that she had nothing to do with the fact that this guy had no class… or balls." -- Ariana at the Multnomah Whisk{e}y Library

A less-than-subtle hint

"It was just a random night, not Valentine's Day or anything. It was a young couple, and as they headed to the table I overheard them talking about what to do in the next year: get a pet, go on vacation, etc. I remember dropping off their food, they said thanks, and then she asked him, 'Don't you want to get engaged in the next year?'

"There was silence for about five minutes as they stared at each other. They moved food around on their plates, picked at it a bit. I refilled their waters but didn't ask any questions -- server instincts kept me away.

"Next thing I knew, she was crying into her food, sobs echoing across the room. I felt for her, this was clearly not the way she wanted this night to go. Her napkins were ripped to shreds, so I dropped off a stack. He kept asking her to calm down, that they might talk about this later. It was heartbreaking; they didn't even touch their food, just paid and quickly left. The whole thing must have taken about eight minutes. He seemed affectionate when they left. I hope they're OK. Maybe they're engaged now!" -- Elena Fort at Fino

The lingering conversation

"It was a Wednesday or Thursday at Racion, not too busy that night. An older couple came in, maybe mid-to-late 70s, and the woman happened to be in a wheelchair. This was about 8:30pm and we closed at 10, but we certainly weren't going to kick them out or anything.

"10pm rolled around, and they were the only ones left in the restaurant. We'd broken down the bar and the kitchen after we checked they didn't want anything else, so we were just waiting for them to pay and leave. They were starting to get more argumentative, though; we could just feel that the vibe was off. The restaurant was quiet, and we could overhear their whole conversation: He's cheating on her. She understands why, because in her state she can't perform as she used to, but she wants an arrangement, rather than have him going around her back with it. Plus, it sounds like his affair is starting to be something more than just sex.

"It got to be 11:30, and we had brought the lights up, we got on our Racion T-shirts, and had had our shift drinks… and probably a few more than that, but we couldn't clock out until the night was officially over, and we couldn't technically ask them to leave. I guess that's the joy of being old: You just don't have to give a shit anymore. Eventually around midnight they finally got the message and left. On one hand, it was super-sad. On the other hand, you know, please get out so we can get food and a drink." -- Justin Siemer at Racion


"Since our bar closed earlier than the legally mandated time, when we did last call our standard was to gratuitously wait for our guests to leave, staying attentive to their needs until the very end. The trickling out of late guests was almost through, except for one couple who sat at the large community table in the middle of the room. We quietly went about finishing as many closing duties as possible, patiently waiting for the couple to realize they were the last, service was over, and it was time to move on. Our manager assured us that it was a sign of great hospitality that our guests were able to lose themselves in their experience and have no awareness of the diligent service we were giving... but that was before the heavy petting started. The woman began kissing the man between conversation -- we barbacks took turns watering them, polishing tables nearby, slowly bussing items to the back, and any other passive thing we could do to get this couple to realize we were waiting on them. The whole experience started to feel a little voyeuristic, especially when the woman decided to straddle the man on the chair.

"The whole experience started to feel a little voyeuristic, especially when the woman decided to straddle the man on the chair."

“As we all stood behind the bar at a loss for how to stop this impending performance without inflicting embarrassment upon them, our manager finally took action. He grabbed their coats from the armoire and began slowly raising the house lights, then cut the music. Honestly I don't think they realized what was happening so much as they decided they needed a bed promptly. In the moments that they finally separated themselves and walked to the exit there wasn't a sound in the room. Typically there would be an enthusiastic, albeit sarcastic, ring of "Thank you, have a goodnight," but even a friendly smile toward them felt wrong. As soon as they were outside and out of earshot we broke out in applause and nervous laughter. "Well that wasn't awkward!" -- Jeanette Connor at the Multnomah Whisk{e}y Library

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Alex Frane is a Portland native who still loves his city. He likes cocktails and wine more than beer. Follow him @franiacdrinks.