Dating dilemmas


Being a tall person, I have had my share of dates who were much shorter than me. I have even dated a few women who were under 5 feet tall. But, those height differences are very manageable and provide interesting stories. The dating dilemmas occur when something surprising happens.

Here are a few I encountered, some funny some not so.

Why must you be so rude? – the first example occurred when I took a date to Disneyworld for the day driving from my home 3 hours away. The dilemma is she was rude to other people, cutting lines, being curt, impatient, etc. I was captive while there, but could not wait for the date to end.

We really must pray before the meal – one of the funniest blind dates occurred when a friend set me up with a minister without telling me. I was not expecting the answer that she gave me when I asked what she did. She was a nice woman, but I was too immature to get past thinking it was a sin to imagine carnal knowledge with a minister.

Prom dates need to pace themselves – I think many of us have had prom dates where too much drinking occurred. But, our double date before the prom started consisted of far too many Screwdrivers. When we arrived first to the prom, my date waved with a big gesture to the other couple when they arrived. When she did she fell backwards and for some unknown reason, I was able to catch her with one arm, six inches from the ground and straighten her up. Talk about scared.

Did you like how I parked my car?  – when dating a college friend, I offended her when I suggested we use her car, so a friend could use mine. She broke our date after I arrived, so I tried to back down a long, hilly and angled driveway. I drove off into a rock garden and my car got stuck. My last sight of her was as she watched from a large window as her father towed my car off his rock garden. 

Where did that horse come from? – as I was sneaking out of my girlfriend’s parent’s house after she moved into their basement apartment, I was unaware her horse was in the field next to the driveway. At 3 am, while pitch black dark, as I edged toward my car, the horse snorted and scared the bejesus out of me. If a horse could laugh…

I guess my audition failed – this actually occurred with the above horse owner. We went to a community play where folded chairs were placed on raised platforms. When we returned from intermission, unbeknownst to me, one of my chair legs moved off the back of the platform. As I took a sip of wine, I noticed my date moving forward in slow motion. In actuality, I was falling and made a huge crash when I hit the floor on my chair. It was indeed funny and the only thing hurt was my ego.

Tell me your funny or surprising date stories. I am sure you can top mine.

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22 thoughts on “Dating dilemmas

  1. My sister set me up on a blind date. I drove, just so I had a getaway car if needed. Looks do not matter, but not looking like a slob does. That was the first sign. He asked me to come in while he got his things together. Strike 2. He asked if I wanted to see his watch collection, which seemed interesting so I followed him …. (never do that) only to be shown his Bong collection. Thank GOD I had a getaway car!! To think I still speak to my sister … seriously.

    • Blair, I thought so, too. My first reaction was “you could not have told me that before I drove 45 minutes to get here?” She would not have gone out with me again if I asked, but I really did not feel like asking after that. I did not want to bump into her father again, although I am sure it made quite the family story. Do you remember that guy….? Thanks, Keith

  2. These are GREAT Keith!!! Loved them!!! Mine is; 14yrs old, lst date, climbing over schools gates to go sneaking out, dress got caught on fences wipped over head and hung me. Had to be torn down, half aphixiated dress in 3 pieces and worst, no bra, and pink Scooby Doo panties. He never spoke to me again!! What? You don’t like Scoobie??? 😉

  3. That is scary and I am sure it was aggravating to a bold fourteen year old, even with the Scoobies. Definitely a rut-ro quoting the famous pooch.

    The horse story involves me climbing a gate as well. Thoughts of falling did pass through my mind. No Scoobies, though.

  4. Note to Readers: A date that did would work out is when my future wife asked me to meet her for a drink with her brother and his wife. We knew each other as her company sublet space from my company and she had been talking with a female co-worker about me – more on that below. Only her brother could make it and they had worked out a signal that if it was working, he would leave early. It must have, because he left and we had dinner. And, the rest is history.

    As for the co-worker, she had suggested to my wife that she would eat me alive and did not think it was a good match. After we began dating, the co-worker told me “I am so glad I got you together.”

    • The crazier ones stand out. I had many blind dates with little chemistry and I am sure the other person would say likewise. Sometimes, I think back and wish I was more mature than I was at the time.

  5. Note to Readers: I mentioned dating 4’11” or less women. At 6’5″ this provides an interesting visual for dancing. I was dating such a person during a college reunion weekend and created a few chuckles. Also, on kiss good nights, I would ask my shorter dates to stand on the first step.

  6. A fellow who had a crush on me kept pestering me for a date. I really wasn’t very interested, but he was nice and he finally convinced me to come over for his home cooked lasagne dinner. He was Italian so I knew I’d be in for a treat. I arrived at his small apartment at the agreed upon time. It took quite a while for him to get to the door and when he did, his hair was wet and he had a towel wrapped around his ample girth. That was the beginning of a very long night. He had not even started cooking yet. To shorten a very long story, we didn’t even begin to eat till around 11:30 at night. (And I had to be at work at 6:30 the next morning.) It was the best lasagne I’ve ever eaten. 😉

    • I hope you had good conversation while cooking for so long. I am glad it was good. My wife was invited once for a homemade Italian dinner and it was frozen lasagna from a package. Sounds like your newly clean date at least could cook.

      • Yeah, he was a fabulous cook and a nice guy, but we just didn’t click. I think the poor guy ended up eating himself to an early death. Oddly, he married a woman called Linda! Last time I saw him, he could barely get out of his huge easy chair.

      • It breaks your heart when you see someone who has made bad decisions that will impact his or her life. You would presume his wife Linda cajoled him to exercise and eat better. Keith

      • Linda, a computer expert today would be a catch. But, you would hope he would be more in shape, with his worst flaw being carpal tunnel in his mouse wrist. Keith

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