Dating Story: He Did This When The Bill Came

Dating Story: He Did This When The Bill Came

I was recently on a date that was going quite well actually... until the bill came. The waitress quietly slipped us the bill and it popped up as a reminder that we had been on the date for well over an hour; time goes fast when you’re having fun. My date, which we will refer to as Tom (mainly because of the foolery he provided) examined the bill with the precision of an HR Block Tax accountant for what felt like 2 whole minutes. Things got a bit awkward when he pulled out a calculation! Bruh. How much math is required here. From my vantage point the calculator app looked more like the TI-83 calculator that I used in 8th grade. After what felt like 5 minutes of long division, solving a quadratic equation and solving for M in the Y=MX+B of the linear equation he concluded that his share of the $98 bill was about $60. Let’s pause here.


This was a bit awkward for me because he asked me out. He picked the restaurant, which was a really nice slightly pricey Cuban restaurant. And call me old fashion but I expected him to pay or at least give me a heads up that we were going dutch, which I have no problems doing. Thankfully for me I never go out without having some money. 

Let’s resume. Once we decided how much of the bill we were each paying he also decided that we should split the tip. I obliged. “Pulls out credit card.” The waitress returns with the receipts and I tipped and waited for him to finish. Phase two of awkwardness commences. The suggested tip listed at the bottom of the receipt was about $14 so my half would have been $7 but I decided to tip her $10. Apparently this was a problem. He claimed that I tipped too much! HOLD UP BRUH! One thing you wont do is tell me how to spent my own money! God was working on my that day because the monologue of a respond that I had prepared in my head decided to stay there. Thank you Sweet baby Jesus for being with me at that time and helping me avoid an angry black women embarrassment. 


Side bar, this restaurant put the bill in cute little cigar boxes so Tom had to reach in order to see how much I tipped, adding to the awkwardness.

Again this situation made me think about exactly what the proper etiquette for paying for dates was. Should the payment arrangement be discussed prior to the date? After this and several other similar dates I think the first date (especially if you met virtually) should be deferred to a coffee shop a local bar/pub or even a park where you can just meet up and chat to test the chemistry. I’m not one to judge someone based on their tax bracket or financial flexibility, so it’s cool to pick an affordable spot of the 1st date or to plan a free date. I spoke to several of my male friends and there is a fear amongst some them of spending on a woman you may never see again, or becoming the a top tier meal plan. I fully understand that concern. My answer to that is to pick a place that is very affordable or look for cheap or free dates, which is really not hard in urban areas. 

Did you go on a date recently and had an awkward bill moment? Please share below.