Date Stories, J

J: Revenge is a drink best served free

Context: I matched with ‘Pessimist’ on Tinder, after noticing he looked like a guy my friend A had gone on a date with. He also had the same name… and worked at the same company… and had gone to the same school… a quick screenshot exchange confirmed that it was, in fact, the same guy! We agreed to meet at La Tasca (classic) on a Friday after work.

Who should pay on a date? It is an oft-debated topic that has been tearing families and villages (and wallets) apart for centuries. It seems like a simple matter, does it not? One little check, two (ideally) rational humans? So WHY is it the year 2016 and this has yet to be resolved? ALSO, why are people still inviting me to play Farmville?!? IT’S NOT A REAL FARM!! EVERYTHING IS A LIE!


…whew, sorry about that! I’m just really, really passionate about not paying for my dates, ok? I’d say, out of the ~56 first dates I’ve gone on since beginning this journey in Summer 2015, I’ve paid for two. In one case, the boy was two years younger than me and using a fake ID. With a different name than his credit card. He had to pay in cash. There are SO many things wrong with this situation.

The other time, it was the guy’s birthday, and I wasn’t about to let him pay for my shit on his birthday. We still split it, though. Do I look like I’m made of money? Ha. Hahahaha. Haha.


My idea is, if you ask me out, and you are interested in going on a 2nd date with me, you should pay. I will do a courtesy pump fake so I don’t look like a total twat, but you should still pay. I might excuse myself around check time to go to the bathroom. Take this chance to pay. I will always offer to pay on the second date, insist on the third, and offer on all subsequent dates. But first dates are full of charm and chivalry and jitters and such, PLEASE don’t get me all worked up about the bill, JUST PAY.

‘Pessimist’ broke that rule for my friend, A. I was here to get revenge. Let’s back it up like the Cha Cha Slide.

cha cha

A had never been on a dating-app date, so when she scheduled one with ‘Pessimist,’ I was there to help her prepare. My advice was as follows:

  • Go in for the hug first. This shows that you’re happy to see him and makes you appear less nervous than you are.
  • In case of awkward silence, ask him personal questions that aren’t too deep, but will make him think and get the conversation flowing again
  • And, whatever you do, do NOT pay. Don’t do it.


So, A went on her date with Pessimist, and it was all going well until the waitress dropped off the check. The $20 check. Just drinks, no food, pretty cheap. Now, Pessimist works in a pretty well-paying line of work, so this should be no skin off his nose. Which is why it was strange when he just let the check sit there and continued talking. A was suspicious, but figured he was just enjoying the conversation, so she kept going. When the waitress came back to pick up the check, Pessimist waved her off.
P – Ahh, we haven’t put a card in yet, sorry!
W – Oh, no worries, take your time!

The waitress walked away, and Pessimist still did not make any moves to pay the check. The waitress came back around again, and Pessimist waved her off once again. The conversation was becoming stale, and A was about ready to head out, so she addressed the elephant in the room.
A – So, I guess we should pay…
P – *shifty eyes* Oh, yeah. I mean, I guess we should… do that…
A –
P –
A – …so, I guess I can pay for half…. *takes out credit card*
P – Oh, I mean, are you sure?!
A – ….I guess….

And so, A paid her $10 share and left. She only spoke to Pessimist one more time, to deny his booty call. GOOD A.


So, when I came across Pessimist, I was determined to make him pay… literally. Now, mind you, I’m still dating the same guy I was way back when I last posted on the blog, so I had NO intention of forming a romantic connection. Just of exacting revenge.

When I arrived at La Tasca at 6:30, Pessimist was already seated at the bar. My first impression was that he was kind of gross. Definitely heavier than in his pictures, not particularly cute, and very gruff. Still, I put on my brightest smile and dove into making the date as great as possible – asking about his family, his vacations, his job, and more while batting my eyelashes and throwing in the occasional hair flip. He fell for it hook, line, and sinker, rotating his body from fully facing the bar when the date started, to facing me, legs spread wide open, even before our hour and a half was up. He even offered me his leftover malaria pills for my upcoming trip to South America (which I politely declined, because accepting leftover drugs from strangers is frowned upon in most social circles).


And we can’t forget about the drinks! When I first sat down, he had asked me what my favorite thing was:
J – Well, all of the sangria is good, but my favorite is the blackberry-mango. Want to get a pitcher?
P – I don’t know about a pitcher… I would probably drink a lot more than you and gip you of your share…
J – *Gip? So he DOES expect me to pay… and he also has no idea how much I can drink… interesting*
J – Haha, you don’t know me. Let’s get a pitcher.

So, we proceeded to order a pitcher, and got to talking. An hour and a half later, I was ready to peace, so my date asked for the check. As the bartender went to print it, he turned to me and valiantly said “Don’t worry, I’ve got this,” and then proceeded to dramatically unsheath his credit card from his wallet as if he was removing Excalibur from the stone. I guess his mom finally paid him his allowance or something?!

The Sword in the Stone (1963) Directed by Wolfgang Reitherman


After he signed the check, he asked me if I wanted to go grab a drink elsewhere. I politely declined, saying that I “needed to get home and do important things.” Clearly my interest level was through the roof! He walked me home, and then texted me the next day, a text that will never get a response. You know what Buddha says – “Once a fuckboy, always a fuckboy.”


I’m still thinking about asking him for those malaria pills, though…


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