Two weekends ago, my boyfriend went out of town, so I had a girl’s night. This consisted of going to an incredible sushi restaurant and then going out for drinks after.
My girlfriends picked me up for dinner, and we took a shot before heading in; it felt like I was a teenager again.
We only had a cocktail each at the sushi restaurant, and they had a time limit, so we left, stopped by the gas station for a chaser, and went to our next destination. A hip mansion converted into a dance/lounge area serving food and drinks.
With no time limit on our hands and several shots and cocktails later, we started talking about the worst dates we’ve ever been on.
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The 5-year relationship that turned out to be gay.
Tess had been in a relationship for over 5 years with the same guy. I met him briefly; he was quiet and didn’t say much. They shared a house with 4 other people and lived in the attic they renovated into a bedroom.
Tess and I worked together at The Olive Garden when she was dating him, and one evening she broke down and told me how frustrated she was with her boyfriend. “We never go out anymore; he’s such a homebody. He doesn’t want to do anything.”
I encouraged her to tell him how she felt; they had been together for over 5 years, after all. She nodded in agreement and sent him a message that very night, telling him she wanted to go out on a romantic date night with him.
A week later, they broke up, and nobody knew why. “Irreconcilable differences,” she told everyone.
Years later, sipping on her fourth cocktail of the night, she opened up to us and said, “I was so excited for that date, I was ready to open up to him and tell him how much I missed him and how I wanted us to be more involved in our relationship. He responded with, Tess, I’m gay.”
They’re no longer friends, but they ended things off on good terms.
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The time I flew out to Florida.
When I was 16, I went on a cruise with my family. I met an incredibly gorgeous guy there, he was a few years older than me, and he lived in Orlando.
We had an epic few days together, he took me to a prom that the cruise was hosting for the younger people, we went to the upper deck holding hands and listening to the ocean, we hung out the next day and went swimming, and we made out several times. Nothing more than that, I was only 16, and it was a family trip after all.
He was a total rockstar, he was even in a band, and I was utterly obsessed. My heart was broken when I went back home.”
So you could only imagine the excitement I felt when we reconnected a few years later, and he begged to fly me out to Florida. He wanted to finally take me on a date. I thought, “why not? what if this is fate?”
A few days later, I was on a plane to Orlando. After several hiccups along the way, I finally laid eyes on him in person. He was sexy as ever. Long hair, rockstar outfit (ripped shirt, ripped skinny jeans, rings on his fingers, etc.), and the sweetest smile on his face.
He took me to the country club, “my parents are members here, and this is the best place to watch the sunset, ” he told me firmly. I knew he was trying to impress me.
Moments later, he received a facetime. Panic was on his face. He immediately made a U-turn; I watched the video on his phone.
Long story short, his dog died. His dad, the pastor that he was, immediately started praying in tongues over the dog to revive it and giving it mouth-to-mouth resuscitation. I watched in horror, unsure if this was actually happening or if it was some sort of sick joke.
Listen, if I come off heartless, my sincerest apologies. I love dogs; I don’t love adults thinking they could raise animals from the dead.
We drove to his mansion of a house, and 6+ hours later, my phone was dead, and I was sitting on the couch wondering how the heck I had gotten into the mess I was in. Neighbors had come to help pray for the dog; my rockstar guy was crying so hard you’d think he lost a limb.
I flew back home that evening.
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The one where he made her pay for dinner.
Jessica had finally decided to go on a date with a guy who had been pursuing her for months.
The restaurant he picked out was extremely nice, and Jessica was pleased with her outfit choice because of this. She hated being underdressed.
However, when he commented how she looked like she was trying too hard, she started to feel a little insecure and got quiet.
Moments later, the waiter arrived, but Jessica’s date said since he’s been there several times, he knew what all the good options were, so he asked if it would be okay if he ordered for them. Jessica agreed, feeling a little excited about him taking initiative after the insult he made earlier.
Jessica tried to be optimistic, but throughout the course of the evening, she couldn’t help but wonder why he had asked her out in the first place. She felt like every other word that came out of his mouth was an insult to either her appearance or her drink choice.
The food arrived, and not only did he order enough food for a small family, but he ordered zero vegan options, whilst knowing that Jessica was vegan.
When the bill came, he asked her if she could spot him; he’d misplaced his credit card.
Jessica never saw him again.
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I’m a firm believer that everyone has to go on a few bad dates to get to the good ones. I’m very curious to hear yours.
Let’s stay in touch. Subscribe to my YouTube channel for lifestyle and relationship content.
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This post was previously published on medium.com.
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