Anne Hunting Love: 5 Worst Dates

Dating is a Battlefield

In my last post, I presented you with 5 dates that were just plain boring. Today, I go one step further – five truly BAD dates. You cannot expect every date to be good or even boring. And let’s be honest, every heroine or hero of a romcom has a low moment where they learn an important lesson and come out better on the other side.  In the quest for love, you’ll inevitably find a “Failure to Launch” when looking for a “How to Lose a Guy in 10 Days.” (Matthew McConaughey stars in both – If you haven’t seen the first movie, don’t waste your time. If you have not seen the second, stop reading, go and watch, and come back. No yellow dress in history has been more impactful.)  

Without further ado, the countdown of the 5 worst first dates I went on: 

 
 

#5 Mr. Wineglass

Mr. Wineglass was the first of the 21 dates and I was excited (and nervous) to start. He had suggested our first date be a weekend wine trip in Baja California (ummmmmm, am I secretly on the Bachelor?), but the beer on a Tuesday evening I suggested. Unfortunately, he let me decide little else. He ordered food and a second beer I had not wanted or asked for, commented on my lack of interest in the food and drink with annoyance, and spent our time together talking about his drinking escapades around the world. NO THANK YOU. 

LESSON: Chivalry is acknowledging I have my own thoughts and opinions, and, in fact, know my own hunger levels.

#4 Mr. 8 Ball 

I had a hard time setting a date with this gentleman – I did not want a drink and he does not drink coffee (or apparently like coffee shops which, in fact, do not only serve coffee). In the end, we met up at a pool hall, my first activity date of the challenge and I was excited. Unfortunately, my skills were rusty and I lost the first two games quickly as he told me he had never been in a relationship and had a horrible history with female Geminis (whoops – proud astrological twin here). Before the third game, he wanted to make a bet: if he won, he got a kiss. I was NOT down with that because no matter what, I had a choice in the matter, and was honestly not feeling it. Mr. 8 Ball got pretty upset when he realized I was not going to take up the bet, which was not a good look. Ironically, it was the only game that night I won. 

LESSON: Winning is fun. 


#3 Mr. Stopwatch

This man said on his profile that he appreciates when his date shows up on time and then proceeded to be 15 minutes late. He commented negatively on my decision to only have one glass of wine on a Wednesday, while he chugged down four beers. An hour into our date, he suggested I spend the night with him and I responded in the negative, claiming my kindergarten students would SURELY notice me wearing the same outfit (they noted when I wore the same earrings two days in a row - an entire outfit would not slip by them). This man, not taking the hint, suggested we find an open Old Navy or order something on Amazon Prime. YIKES – if this does not scream desperate, I do not know what does. He texted me MINUTES after I got in my own uber saying he hoped he did not seem like someone who was only looking to hook up – if the shoe fits, Mr. Stopwatch. 

LESSON: Amazon Prime does not have all of the solutions.

#2 Mr. Gorilla

This date was the second date of the day on a Thursday, and the first date had been extraordinarily fun. Mr. Gorilla heard my academic and personal history and felt the need to prove his intelligence, delving into topics I knew intimately. When I tried to explain my recent graduate thesis on elementary education in the Korean peninsula, he lectured me for fifteen minutes about the history of the peninsula, after which, I asked for his sources – videos on YouTube. When he went into a deep discussion (again from YouTube clips) on slavery in the United States, I had to beg exhaustion and leave: I just couldn’t. 

LESSON: Mansplaining is exhausting and unnecessary. Dudes dating out there: if she says she knows, believe her and shut up.  


#1 Mr. Circus Tent

Get ready, readers. This one is a DOOZY

Some truths: 

1. Attending an opera, while seemingly romantic, is a terrible date idea because it essentially has you sitting silently next to a stranger for four hours. 

2. Operas about an emotionally abusive man slipping into insanity ending in a double suicide are even worse for dates. 

3. Men who ask you to search “CBT” on incognito mode (which does not stand for Cognitive Behavioral Therapy like I thought) are not men you should go on dates with. 

Against all of these truths, though, I agreed to this opera date and tried to go in with an open mind. We met for brunch before the opera and once again, this man was uncomfortable with my advanced degrees and would not let me speak. After trying to insert myself into the conversation, I gave up and sat calculating how long I had before we were seated in the theater where he would not be able to talk.

The joke, though, was on me. The program listed the run time: 3 hours and 45 minutes with two twenty-five minute intermissions. You best believe I spent all of those fifty minutes in the bathroom, avoiding my date at all costs, especially after he did not recognize that the main character singing, “If you say you don’t love me, I’ll kill myself” (again this was a VERY dark opera) as emotional abuse. You best believe I essentially RAN out of the Lyric Opera of Chicago, not even letting him walk me to my car. 

LESSON: Trust your instincts: if all signs point to a poor date before you meet someone, it most likely will not be better once you meet in person.   


WOW. We survived and still believe in a thing called love. As I said at the beginning, the bad and boring are necessary stops on the quest for love and I was lucky at the level of “bad” date I experienced. Being a single person (particularly a woman) and meeting a stranger for a drink or dinner is physically scary – a lot can happen. Thankfully, none of the men I went on the 21 dates with posed a physical threat with me. That being said, please be safe out there as you seek out your own love stories, everyone.

Now with the boring and bad are officially out of the way, and we can talk about the good stuff: the five dates that gave me hope. Readers, they exist and I cannot wait to tell you all about them! 



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Anne Huntington