As anyone who’s tried can attest, the dating scene in the Keys can be, shall we say, rough. For every good date, it seems that there are 10 bad ones. With Valentine’s Day serving as a reminder of love and all that was meant to be, sometimes all we can do is laugh as we also look back on the connections that were most certainly not meant to be. With that in mind, Keys Weekly presents some of our readers’ most comical dates. And in the interest of preserving the last scrap of mystery in our tiny island community, these were better left anonymous.
“I was set up on a blind date. The day before the big night, I looked him up on the MCSO website. At the bottom of his arrest record, there was a button that said ‘next.’ He had a whole second page of arrests! Anyway, we’ve been together for seven years now.”
“Many moons ago, I head-butted a guy at Irish Kevin’s. I ended up marrying him.”
“On one of my first dates after moving down here, I was hanging out with a girl and we were at dinner having a good time. She asked me what my zodiac sign was. I didn’t have a clue. So she asked me for my birthday and looked it up. Apparently I was an Aries. Based on that alone, she said we weren’t compatible. I split the check.”
“This was the first, and only, time I ever asked someone out while I was at work. I worked at a tourist attraction, and she was in one of my tour groups. Afterwards, it was pretty obvious she was hanging around to talk to me more. I asked if she wanted to get dinner later that night, and we went out and had a great time. We went from dinner to the beach and back to hanging out at my apartment. During dinner she mentioned that she recently split up with her boyfriend. When she left, she mentioned that she’d be pretty busy when she got back home and probably couldn’t keep in touch. I was okay with that, and just enjoyed the time spent together. At 2 a.m., I got a phone call from her. She was extremely upset, and told me her boyfriend – apparently not an ex, like she had told me – had tracked her phone and was now furious with her. She ended the call by saying, ‘So, I guess I can keep in touch with you after all.’ I hung up pretty quick.”
“I once took a girl to the sandbar on a date. The problem was … she wouldn’t walk on the sand.”
“Once upon a time, I accidentally ended up with three dates to my best friend’s wedding, and they all showed up. My first date was a woman I had liked for a long time, but who always had a boyfriend. When she became single, I asked her to come to the wedding as my date. About three months before the wedding, she messaged me to say she had a new boyfriend and would be bringing him to town with her, so needless to say, it wouldn’t be appropriate to go together. About a month after this, I met a new local woman and slowly started dating her. About a month into dating, I asked her to be my wedding date. She wanted to, but couldn’t get her work shift covered. Since I still had a plus one to the wedding and was the best man, I decided to ask one of my best female friends to go with me, as she was planning to come to the reception later anyway. About three hours before the wedding, my girlfriend called to tell me she was able to get out of work and go to the wedding. She was extremely happy, but my third date was, understandably, not. My third date almost refused to come because she wouldn’t have a dance partner, but did eventually end up showing up. Needless to say, when the three mixed together, nothing good happened. Word to the wise: if you’re going to have a wedding date, there’s a reason the card says ‘plus ONE.’”
“I had been trying to set a date with a woman in Key West for a couple of weeks. We had texted back and forth quite a bit, and she told me how excited she was to see me and get away from her friend group, including her ex-boyfriend. We set a date to meet at a bar in Key West, but when I drove down there and walked in, I found her shooting pool with all her friends. I stayed for one round, but near the end of the game she let slip that one of the guys I was playing against, was, you guessed it, the very same ex-boyfriend. As soon as the 8-ball sank, I left.”
“A guy asked me to go to the high school football game on our first date. I told him I could go, but my dad was going to drive me and pick me up as soon as the game ended. We’re at the game, and everything is going fine. Towards the end, I see him talking to another girl. When I asked him why, he said ‘Well, she’s my date for later because you have to go home.’ I never went out with him again.”
