Bad Date Files: My Worst First Date

I originally typed that title as The Worst First Date when I realized that is too bold to universally declare. My is much better. This is about my worst first date – a big distinction considering I may run low on material this month and eventually get to sharing some of the worst dates that were not first-time meetings. After multiple stints of online dating I really thought there would be greater contenders over the years, but in my mind this still holds title rank.

It remains the only bad first date I have ever abruptly put an end to before the natural conclusion. This came up recently with Stef, and despite some bad dates on this last go-around for, I am again reminded my all-time worst first date did not even last 20 minutes.

Despite accusations of a steel trap mind, I am having trouble recalling exactly when this date took place, but roughly in the decade ago timeframe. (definite downfall of multiple breakups and re-connections with same guy, the timeline can blur.) It doesn’t matter a ton and for purposes of storytelling I will declare I was 21+ and it was in a period when college boyfriend Mooch and I had broken up, again. In this period of singleness I was on the receiving end of much pressure to move on and get out there on the dating scene again. One day the morning show I listen to decided to play the dating game over the radio while I was tuned in. This radio station is known more for 60s/70s/80s classic rock and its main fan base skews a little older than my peers. I was listening for entertainment and not thinking there would be any potential interest for me. They requested folks to call in and talk about themselves and the DJs would help prompt if needed. Anyone listening could call in and get phone numbers/leave their number/go on the air themselves.

Most callers were in their 40s but then GA came on the air. 26, (age appropriate, check) 5’11” 160 lbs with brown hair and blue eyes, (I’m interested) likes basketball and baseball, (check and check) and works in I.T. for a famous non-profit (very admirable). Surprising myself, I pulled over and called the radio station to get his number. The producer wanted me to go on the air as well, but since one of the lead DJs is a family friend I thought that would be way too awkward. Their rules were to only give out guys’ numbers, which seemed strange rule in an age of caller ID, but I guess if I was super paranoid I could have called from a blocked/different number. I had already gotten to this point, what could go wrong calling a random stranger from the radio?

It took me 3 days to get up the nerve to call GA and another day to have him respond to my super awkward answering machine message. (A welcome change from the online fellows that get crazy if you don’t immediately respond to a message.) We chatted for a bit about some local news and a little of our background/interests but I needed to get somewhere so it was a pretty brief, maybe 10-minute call. He asked to talk again and seemed interested in meeting up. We talked the next day for more than an hour about our shared love for the Milwaukee area and agreed to meet for a drink later the next week.

Based on our respective locations I suggested Von Trier’s would be convenient, with the plus side of it being my favorite it having a great selection of tap beer and free popcorn. Due to having to circle for a spot and parallel park (Ugh, how I suck at parallel parking) I was about 5 minutes late when I walked in. There were not a ton of people there and as soon as I entered and scanned the room he stood up from a table and we mouthed name inquiries to each other. Let me continue setting the scene by adding he was wearing a baseball cap backwards. Now 26 is young and I have nothing against hats, but on a first date, really? I am known to let a lot slide, and yet that bothered me.

GA already had a beer and the waitress brought popcorn (YES) and I ordered a frambiose lambic. We had a few minutes of some general chit chat about our respective days and started talking about work and school. Here is where things began to run foul. He did not really like his job, but was staying there as they contributed to his grad school tuition and his parents would not chip in. You see, he went to fancy private university and they felt shelling out for that degree was enough. His parents also bought a rental property so he (and other siblings) could live near campus with friends (and where he continued to live cheaply after graduation). Since his parents were not covering his graduate degree, he had to “slum it” at the local state college (ahem, where I had gone to college).

It is right about this point when it occurred to me I was on a date with a stereotypical, overprivileged,  frat boy douche canoe. Then I was ashamed for making such a harsh, snap judgment (judgement? GAH why are both acceptable spellings?) I tried to steer the conversation to a less exasperating topic, but we only got into a petty argument over the NCAA exploiting college athletes.

The waitress refilled our popcorn and brought the little black book with our tab. I got out my wallet (I have never been convinced a guy should HAVE to pay, first date or not) and was told to put it away and that he had it. Then he opened the book and looked at the tab and got angry that my beer was $7. (From a guy that milked his parents for private school tuition!) I was so taken aback and defensively explained I was fully aware it was $7 when I ordered it and reminded him I had offered to pay for it.  Hell, I specifically chose the location so I could order this particular beer. It didn’t end there. I was on the receiving end of a crazy tirade about being “high maintenance and how all chicks have unreasonable standards.” Let me reiterate this flip out was not teasing in jest, and THIS WAS ALL DUE TO ORDERING A TAP BEER. Yes, it was certainly one of the fancier beers offered, but I just as easily could have ordered a $15 martini. I contemplated pulling out some cash just to stop the arguing, but I didn’t. I slammed the rest of the beer (not difficult considering it was a small glass) got up, told him he was being an asshole and left. The 20-minute date I never saw coming was over.

For the record, my dad is the only man allowed to call me high maintenance and I still turn off the radio whenever the morning show plays the dating game.



Filed under (I Like Parentheses), A Whole MONTH, Fine Red Whine

4 responses to “Bad Date Files: My Worst First Date

  1. WOW. Quelle fucking douche! (Also, $7 is not even remotely expensive for a beer, douche-nozzle.) I have no first date story that comes close to this one; congrats?

  2. My question is, why did the waitress bring your tab 20 minutes in? Maybe she could tell it was not going well? $7 may have been a little pricey ten years ago, but yes, dude is still a douche canoe.

    Do you remember the date I had where, when I offered to split the tab, he actually had the nerve to say, “Oh, you had one more glass of wine than I did…”? Yes, I did, sir, because you were late, and I PAID for that first glass at the bar, before we were even seated. It’s not on the fucking tab that you’re nickel and diming me about. Dumbass.

    Ugh. Dating. Yes.

    • Bars here often bring tab right away, if you order another round they just adjust and bring you a new tab. (left out of the story – the waitress did bring it and ask us to settle then as there was a shift change and they were trying to close out a drawer.) $7 was pretty pricey 10 years ago, but I refuse to offer any defense to that fuckwit (see I really like using that word now.) I will never understand how a guy thinks arguing over a tab is attractive whatsoever.

Agree? Disagree? Love the attention either way. First time commenters are moderated. I think. Or maybe the blog just eats comments. I haven't really figured this all out yet.

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