Dating Disasters: ‘I doubted whether he was interested in me until I received a message in the middle of the night’

In Dating Disasters anonymous readers share their most embarrassing, cringeworthy, and dramatic dates. This week: the Romeo among millennials.

I had known him for years. He was the hottest guy at our high school. Every boy wanted to be him, every girl wanted to be with him, and I... I was just there. I was one of those girls who blended into the crowd and did everything to stand out as little as possible. I don't think he was even aware of my existence until the moment I added him on Instagram years later. By then, I was well into my twenties, completely out of my shell, and quite fun to be around. He, in turn, was still a dream to look at.

He followed me back almost immediately and quickly developed the habit of responding to a large part of my Instagram Stories, so I developed the habit of posting Stories that I knew he would respond to. Oh, love in modern times. Shakespeare must be turning in his grave if he knew what had become of our hopeless romantics.

After weeks of back-and-forth messaging, I thought it was time to meet up with my high school crush. After all, we weren't 14 anymore, so an internet relationship wasn't exactly the goal I had in mind. Unfortunately, for some reason, we just couldn't seem to set a date. He was so evasive that I wondered if he was even interested in me, but he kept appearing in my inbox constantly. What was his problem?

That answer came sooner than expected. One evening, I was completely fed up with his vague behavior and challenged him one last time to come over. He said he couldn't, his friends were waiting for him. Unbeknownst to me and fed up with his vague behavior, I flopped onto the couch and started a movie marathon until I received a message from him around 3:00 AM: ’I'm at your door.‘

This had to be a joke. It was the middle of the night and it was pouring rain. I walked to my balcony and sure enough, there he was: Romeo himself. Soaked and, from what I could see, dead drunk. I opened the door for him and he drunkenly slalomed towards my couch. This was the first time I experienced the saying ‘only children and drunk people tell the truth’ in real life, because even before I could sit next to him, he finally admitted the reason for his delay: he had a girlfriend.

Sorry? What are you doing under my balcony in the middle of the night? On my couch? I didn't even have time to respond to this confession. He thought this was a good moment to lean in for a kiss that I expertly avoided. For a brief moment, I felt sorry for him. There he was, wet and drunk, about to throw away his relationship.

Not long after, I sent him home and the next day I saw that he had removed me from Instagram. Ha, as if I was the problem in this situation. I saw him one more time walking with his girlfriend on his arm. Whether he ever told her about his nocturnal escapade, I don't know, but I'm glad we both got something out of it. He gained some renewed respect for his relationship and I got a good story for the Friday drinks.

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