Rocky Love Emily?

We're back with Date Night Fridays and you're not going to want to miss this one...and it's from a guy! 

I’ve never really been that into Halloween, so in 2005 when one of my best friends invited me to a Halloween party with a bunch of his soon-to-be dentist friends, I was somewhat reluctant. But I went, probably donning some stupid wig that was indicative of my perennial laziness about the ‘holiday’. Fast forward a couple of hours after some beer pong and flip cup, I was having a great time! Not only that, I was eyeing a girl from across the room, in the back of my mind hoping I hadn’t unknowingly added beer goggles to my costume. By the end of the night I was introduced to Emily, had her number, and had all but put an appointment in my calendar to call her on Tuesday, waiting the requisite number of days to not seem too interested, but not disinterested. Side note – I will not forget her name since throughout the following week my friend, and office mate at the time, would randomly chant Rocky loves Emily, a la Three Ninjas.

Tuesday had come, we spoke, and scheduled a date for Friday. Now, this was only a few months after graduating from college so I had not yet moved to NYC, but rather was still living out in the suburbs with my parents. This meant that on weekends and especially when going on dates, I needed either to arrange to stay with one of my few friends who already did live in the city, or that I had to do everything I could to make sure the date went really well. We went to a restaurant near her apartment on the upper east side. This was before I had established my ‘drinks only’ rule for first dates, and in hindsight this night was probably a key ingredient in the generation of that self-imposed rule. The vibes were pretty good, decent conversation, limited awkward silences. After the plates were cleared I excused myself to use the restroom.

When I got back to the table, she was putting her phone back in her bag and looked at me as if to say, ‘well I had to entertain myself somehow while you were gone’. Conversation continued and at this point, I was pretty sure this date was going to continue and I was ready to cancel my reservation at my friend’s apartment, opting for Emily’s instead. Back at her place we had another drink and I was fairly certain that this night was, and was going to continue to be, a success. In fact, it even got to the point where it was discovered that I did not have protection (I never thought it was right to be that presumptuous on a first date). Bummer. But what a great night. I knew I’d have another chance.

Emily got up to go to the bathroom and I checked my phone and was going to write a message to my friend confirming that I would not need him to leave a key with the doorman. But I had a message. And it was from Emily! Had she found a condom in the bathroom? Then I read it and was immediately confused. Then it dawned on me. Remember when she was putting her phone away at the dinner table when I was coming back from the bathroom? A text message she had clearly meant to send to a friend found its way to my inbox instead. Not a big deal, the date went so well, it couldn’t say anything bad, right? WRONG.

 "At dinner, then my place. Don’t know if I like him. Want to die…"

WHAT! Here I was half naked in her bed and she didn’t know if she liked me?? I didn’t know what to do. Should I tell her? Should I just leave? Then I remembered I had nowhere to go because my buddy was asleep by now and had not left a key for me. I was also not sober so getting in the car and heading back to the suburbs was out of the question. So, I awkwardly stayed, awkwardly slept, and awkwardly left as early as I could in the morning. I had to make sure she knew what she did. So, that afternoon, I forwarded the message back to her and she tried to play it off. Needless to say, Rocky had no love for Emily. This tale of dating discomfort comes from Dan, 30, New York.

If you have a dating disaster to share, email me!

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