It’s the debate of the century: Who should pay on the first date? It used to be very obvious: The man. And if he didn’t, he’d be the talk of ladies-who-lunch date across the city. Chivalry is something many of us hold near and dear to our hearts, and often it’s not about the actual financial aspect, but more so about the guy showing an investment. About the guy showing us ‘We’re worth it.’ About the guy showing us that chivalry is not dead.

But with millennials going on dates every damn day, and women truly embracing equality, the lines are now blurred about the right end-of-date payment etiquette. Do you reach for your wallet to fake offer? Or worse, to real offer? Do you insist on splitting half? Do you leave for the washroom when you know the bill is expected to come to avoid the whole awkwardness? Or do you sit there, mum, as you wait for him to reach for his wallet like a true gent, knowing that if he doesn’t cover the bill, you likely won’t see him again?

No matter what your payment (or lack thereof) method of choice, here are some of the most cringeworthy stories we’ve heard from daters in Toronto when it comes to the bill arriving on a first date. Perhaps these sitch’s will make you feel better, but perhaps, maybe worse.

Tit for tat (minus the tit)

They met for drinks on but a Saturday night at a bar in her area. She wanted to keep it close to home because he was best friends with a boy she bedded/had, had “a thing” with but a month prior, and wasn’t sure how she felt about this whole arrangement. They matched on Bumble earlier that day so she thought she’d give it (and potentially him) a go. They took back a few stiff ones, shared a plate of frites and got their flirt on… Hard. Conversation and chemistry were there, so they decided to ask for the bill so they could head to a more private bar downtown for a nightcap, before calling it a night.

She was impressed when – after he asked for the bill – she noticed he had his Visa out and ready to hand to their server. That is until, after he paid, and said, “You can grab the next one.” The date suddenly turned into a business arrangement. They got to the next spot, and her sobering sips killed her love buzz, knowing that this half of the date was on her. She would have offered to grab it anyways, but it was the fact that he demanded it that was the issue.

The life and times of a bachelor

After sending suggestive messages back and forth on Instagram, they decided to meet for drinks (re: sex) on the Ossington strip near his bachelor apartment. He insisted she meet him somewhere close to his home (that should have been her first red flag, but rosy-shade glasses tend to mislead the tenacious.) They had a few drinks each at the dive bar, and when the $50 bill came to the table, he took out a $20 and tossed it down, leaving her to cover the rest, plus the tip.

Just for a second. Just to see how it feels. Thrown and turned off, yet still finding him hella attractive, she asked if he wanted to accompany her to an open-bar event she had. She figured she could at least get a cab ride to the event and free booze, since clearly he wasn’t the type to treat and the night was still young. After he took back a good seven or so free beers, and her tipsiness made her momentarily forget his cheapness and lack of chicness, she asked if he wanted to get out of there and head back to his. “Sure, but you need to get the cab,” he insisted, “I got the one here.” Cheque, please.

Two weeks later she was horny and though the sex was meh, her Instagram crush on him went on for so long she thought she’d hit it one more time. They met at another dive bar near his place for eats and drinks. She ordered a wrap and a few vodka sodas during the two hours (too many) that they were there. He ordered water. Needless to say, that’s the last time they saw each other.

Out of towner/out of mind

He landed in from the airport for a few day stint to visit her and stay at her place. He opened up Uber and was quoted around $50 for the ride to meet her for a drink by her place. He called her, surprised at how much it was, though she reassured him that it’s way cheaper than a cab and actually rather reasonable. “Ok, well you’re paying for our drinks tonight then,” he said, before hanging up and heading to meet her. A freelancer who lives paycheque to paycheque she nervously awaited and made sure to keep her drinking to a minimum. He racked up an almost $100 bill (hungry after the flight, thirsty AF,) and she nervously got out her card to pay when the bill came, half hoping it wouldn’t be declined, half hoping it would be because she didn’t know how to tell him she couldn’t afford it – after all he did come to see her. He did Uber to her. The card went through. He didn’t say thank you.

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