This article was originally published on the website Rocky Parenting. I was a finalist in their Valentine’s Day humor writing competition, “Awkward Love.” I think we can all relate to the frustrations and disappointments of dating, whether recent, long ago, single or divorced.

I was determined to be proactive about improving my romantic life. Since I was not meeting many men “organically” I decided I would give online dating another shot. This time I would be lenient on the looks and focus more on finding a nice, sweet guy.

During a brief pre-date phone call with my potential match, he mentioned that he sometimes wore glasses and sometimes did not. His hair could be straight or spiked, his dress style casual or cool. He would surprise me. And that he did…standing on the corner sporting yellow khakis, pink polo shirt and feathered, chin-length hair reminiscent of Shaun Cassidy. With one elbow propped up against the building in a Sears catalogue pose, he was nerdy for sure, but maybe nice and sweet. So I tried not to be judgmental.

My rule on a first semi-blind date is to meet for drinks, and maybe a quick appetizer. That way, one, you are drinking, and two, you can escape after a very short commitment of time. Since wine can be considered classy and not a blatant attempt to numb the nerves, we both agreed on a cute Italian café that had a “great selection of wines.”

We were seated at a small table for two and started looking over the drink menu. That night he had decided not to wear glasses, which is a logical move if contact lenses are substituted, or if you are able to see without glasses. The menu was written in at least font size forty, and still he couldn’t even make out the titles – so I had read the options and order for him. Despite the geriatric ordering, our conversation over the wine was pleasant. And I was pretty sure he could at least make out the features on my face.

Telling what I thought was a riveting story, I could see he was losing interest and even looked disturbed. He excused himself from the table and was absent for quite some time. When he returned, his easy-going 70’s sitcom demeanor was replaced with the look of a scared little boy who just broke one of your good vases. He informed me he had been to the dentist the day before to get a tooth fixed, and said tooth had fallen out while he was eating the appetizer I had ordered for him. “Don’t worry,” he said. “I put the tooth back in.”

Once the red blotches on his face faded, he suggested we continue the date to another location. I felt badly for him and actually admired his strangely chivalrous attempt to make it work. So I agreed to go.

He chose a romantic Spanish tapas bar, because I guess he was feeling pretty sexy. Another glass of red wine was too much for his 110 pound frame, and he started giggling uncontrollably. Okay, maybe I was enjoying the idea that everything I was saying was hilarious to him. One literally too funny of a joke and the tooth popped out of his mouth, arching over the table and sliding across the Spanish mosaic floor.

“Oh my God, my tooth!” he said, no longer giggling, and ran to the general vicinity where it had landed. Patting the floor feeling for the object like the visually impaired man he chose to be that night, he wasn’t even close. I could easily see the tooth from the table and guided him along.  “No, more to the left. Now up. Nope, too far.” Barely affected by the wine (and nowhere near 110 pounds) I soberly stood up and stretched over him to grab the slimy tooth as fast as I could. He was clearly humiliated, and the date was clearly over.

Walking me to my car in the parking garage, he informed me what a great time he had had and asked if I would like to go out again (?!). As I tried to come up with the right way to say Hell NO, he handed me the millennium version of a mixed tape – a CD collection of original techno music he had produced specifically for me. Apparently he was waiting to see how the date went before he decided if I was worthy. Before I could answer, he planted his missing-tooth mouth on mine. Unshaken by the mishap, he tossed back his feathered hair, and like a wanna-be teenage heart throb on Tiger Beat magazine, gave me a wink and scampered out of sight.















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