To Pay Or Not To Pay?

“To be or not to be? That is the question.” Hamlet ponders this existential question while deeply immersed in decisions regarding betrayal and revenge. Ultimately Shakespeare shows us that revenge results in coldness and loss for all involved.

I teach Hamlet every fall to a group of hesitant and doubtful seniors who are preparing for some version of independence in their near future. We talk about what betrayal means and how and why revenge is never the answer. I hope that they also apply that lesson to their future endeavors. I hope that I can too. I definitely need the annual reminder.

One moment that I truly dread about a date, especially a first one, is the moment when you know it is ending. When the bill arrives. While I do believe in and enjoy chivalry, I do not believe that men should be the only one paying for first dates. Chivalry is much tougher to achieve than simply paying for a drink or a meal. So “to pay or to not pay” becomes the (not always existential but more often) quintessential question.

Yes, I sometimes wish for the opportunity to ponder the much more fun end of the evening question, “to go home with or not to not go home with?” But that fun, sassy quandary has never been the [first date] question. Never. Sad, huh?

Anyway, back to the much more boring and logistics question. The bill arrival is awkward so I dread it. That is just one reason why I prefer and usually suggest a coffee for a first date. Coffee is cheap. I can get my own cup, if I am early enough, and avoid any type of bill boggling. I can leave quickly if I want to, without even needing to await the arrival of the bumbling bill.

But I have been on enough dates that are at bars or restaurants where escaping the bumbling bill just isn’t that simple. Here would be my preferred method:

But I have never been able to bring that awesome plan to fruition. Not yet anyway.

I recently met a man at a bar for happy hour. What does that mean to you? A couple of drinks and maybe even an appetizer or two. Spontaneous conversation?

I arrived at the same time as him so we headed to the bar, him carrying a 3×3 black skinny case of some sort with him. I was curious. He slid it between his feet and the bar, sort of what a woman would do if the bar had hooks, but his case was tall and slender and leaned perfectly up against the wall of the bar. I supposed he had it for another engagement and that it had nothing to do with our time together. I was wrong.

We each ordered a beer and began chatting about one of my least favorite first date topics: how emotionally unavailable and disappointing all of his prior dates have been. He complained, “Why don’t women want to go on real dates? Why just coffee? Just coffee is no fun.”

Not wanting to betray an entire gender by pretending to know their minds, I said, “Well, I do not feel qualified to speak on behalf of all women, but I happen to suggest coffee often because it is a simple and quick way to see if there is a connection. If there is a connection, then I would be more willing to make a bigger commitment on the next date.”

“Ok, so we do the first coffee date and that goes well. Then we do dinner and that goes well and then they are done and just can’t seem to go any further for a third date. Women are so afraid to go deeper. Why? What is wrong with women today?”

Wow. He really knows how to charm a woman with this kind of talk, huh? I wonder what additional research he has done to feel confident enough to sum up all women. And just what is he doing on that second date??

Just as I was about to suggest, “Maybe these women didn’t feel a connection you,” he piped in with, “Or maybe they just want a free meal. Women just expect men to pay.

OMG, did he just make the bumbling bill situation even more awkward?

But I didn’t wonder enough to ask. I changed the subject by asking to see the bar menu.

While I perused the menu for a great share item, he pulled up from the ground his 3×3 black thing. He is an artist by trade and thought I might enjoy seeing and hearing about his work. For forty pages.

Now, at first I was intrigued and would have actually enjoyed quickly scrolling through it, asking questions if I had any. But I got background info on inspiration, on location, and on all kinds of other tidbits regarding all 40 pages. Obviously, I had to order another beer. But I still wanted that appetizer too because I was ravenous. So around page 32, I attempted to turn my attention back to the menu. No luck. My distracting tactics work well on babies and high school students, but not on this passionate artist.

Once he completed his artwork sales pitch, he suggested that we get a table. I suggested that we stay right where we were. First of all, I am a bar girl and prefer that scene. And second of all, women’s soccer was on the tv. When does that ever happen? Not that I was glued to it, but I thought it was really cool to have as a background. He said, “Nah, let’s get a table and make this a real date.”

Does agreeing to meet for happy hour mean getting a table? Does it mean a dissertation on artwork? No, of course not. I should have left after the beer. But, like I said, I was starving!!

So the bumbling bill arrived. Damn it, am I going to have to bumble with the bill two times tonight? Yes.

The total for our four beers, two each, was $17.84. So $22 with a tip, right? Well, he pulls out a few bills right away and lays down a tenner and says, as he shuffles the remaining bills, “I know I owe more than this but I do not have any smaller bills.” Bumbling at its best.

I said, “No worries, (even though I just suffered through a dissertation on his artwork and facilitated a therapy session about his online dating experiences) I will pitch in the extra for the tip.” I had a red flag waving…he is seeking revenge for all of the previous times he has to pay…but it was low and faint, pink even, so I shooed it away, mostly because I felt famished.

We got our table and ordered a skillet of fajitas to share. We also shared a couple of laughs and the conversation wasn’t bad. Much better than the black case art lecture that I suffered through.

Turns out he also makes icons. He showed me his icon pictures on his phone as he doesn’t include this type work in his portfolio because most of his dates do not know what they are. Turns out I do. I am Greek and actually display two of these icons, depictions of key players from the Orthodox faith, in my home, for decorative and nostalgic purposes. I also wrote a paper on the history and function of icons. For fun and out of curiosity. 🤓 So while we did bond over that commonality, I felt tricked, just moments later, as his quest for revenge became crystal clear.

When the second bumbling bill arrived, which was a whopping $25, so $30 with a tip. That MF’er started doing the ten dollar bill shuffle again. “Well I only have tens and if I put in two, then I will be paying $20.”

Thanks for the math. So, let me get this straight, you don’t want to pay more than your half (again) but it is fine for me to (again)? But what about our shared love for icons? Want to arm wrestle for it?

I can be witty in my head but not quick with the tongue. Why didn’t I suggest he ask for change? No I felt betrayed and so naturally went for the jugular with hopes for my own vengeance powered by guilt.

“Why don’t you keep your money? I’ve got it.” That will really get him, right? He should be feeling really guilty now, ready to right his wrongs and end the evening on a leveled playing field.

No, of course not. My passive aggressive tactics, like my ineffective distraction tactics, backfired on this artist, and now I am the idiot because he says, “Oh, ok. Thanks!”

Revenge. Like Shakespeare proposes in Hamlet, everybody loses. I lost a few dollars and he lost the shot at a second date.

By the way, I totally could have taken him in the arm wrestling contest.

11 thoughts on “To Pay Or Not To Pay?

  1. Great read Dorothy…i truly enjoyed it…never knew you to be so funny!!!

    Anthony “Tony” Washington


  2. Love and respect your independence your perspective and the levity that you bring.
    I’m going to have both of my daughters (Junior and Senior in College) read your blog. Wishing you well always


  3. Wow, I can’t believe there are guys like this out there. And here I thought dating was rough for men. I want to reach through the screen, back in time, over to that bar and slap that guy.


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