The 15 Minute Dating Blog

by Gregory Smith.

As a single person, we all make mistakes out in the dating world. If you are freshly single, you tend to make some fairly stupid mistakes related to etiquette – like assuming too much about a woman or a relationship, or being nervous, or not really knowing what you are doing, etc. For those of us who have been around the block once or twice (ha), being someone’s WORST DATE EVER takes on a whole new meaning. Although it can be quite an accidental art form, in most cases it is just flat out stupid. Part of the majesty of being single is one’s ability to go out and make dumb mistakes … not repeat them … and hopefully laugh about them later. As long as you learn from your mistakes, you’re fine.

I’ve lived with my present girlfriend for several years – and I’d say this relationship (among other things) brings me stability. Prior to her, however, I went through phases where I found myself in various highly entertaining situations … not all of which turned out well. For example, what I’m about to describe is an evening where I’m quite positive I turned out to be THE WORST DATE EVER for the woman I was out with. I, myself, have been out with different women who could compete for being MY worst date … but I thought it would be fun today (New Year’s Day) to write something critical about myself. ;o)

Cindy was a tall good-looking redhead – several inches taller than me, in fact. I had known Cindy for roughly ten years … and for quite some time our relationship consisted of us hooking up maybe once or twice a year for a date which almost always ended up in screaming hot sex. I didn’t see her more than maybe twice a year because she lived in Santa Barbara – which made her “geographically undesirable” in terms of being a regular girlfriend or lover. Neither of us wanted to trade in our respective jobs and move – as we just weren’t that interested in one another. We had sex … great sex … but that was where our mutual interest ended. She was also pretty fun to party with – we’d usually go out to a restaurant or club, and party pretty well before the real entertainment got started at either her place, or at my hotel.

So on one such six-month-ish encounter, we were out at some high-end Mexican restaurant in Santa Barbara that I had never been to – and Cindy insisted we order a pitcher of margaritas. I love margaritas so I was all for it. We sat there for several hours having dinner, and downing margarita after margarita. Now for whatever reason – that night we both drank way too much … especially me. I remember telling Cindy that I was too drunk to continue going to different places – and her outstanding solution was for us to go back to her place, and get naked.

Cindy rented what is known as a “granny cottage” … which is a tiny little separate house located on the same lot as her landlord’s house. As we were walking up to her cottage, she told me she wanted to have a cigarette … and so we sat outside while she lit one up. Now don’t ask me why I did this (because I absolutely detest smoking) but she got me to take several hits off of her cigarette – and being a non-smoker who was really, really drunk … it gave me the spins. Several minutes later I found myself throwing up on her lawn. [Throwing up is not a very attractive thing to do on a date.] She sat with me for a while until I was done barfing … and then she brought me inside. I rinsed out my mouth … borrowed her toothbrush … gargled … but I’m quite sure that I still smelled like an ashtray-vomit combo.

To Cindy’s credit, she was still in the mood for me to work some magic on her. I remember her telling me that she was going to take a quick shower, and that she’d be out in five minutes … and that I should take off all my clothes, and wait for her in her “bed”. Her “bed” was not really a bed … it was like this six-foot couch that had an armrest on one end. [She lived in this dinky little granny cottage, and there was no room for a bed … her bedroom was her living room.] I was still hammered at this point – and Cindy was now in the shower. I remember taking off my clothes, and looking at the couch-type thing … wondering which end our heads were supposed to be at. I thought to myself, “let me lie down for a bit and rest while she showers …” and so I did - I put my head at the end of the one-sided couch where there was no armrest. Of course, as soon as I put my head down – I completely passed out.

For whatever reason, I woke up at 4 a.m. – and looked next to me, and saw Cindy’s feet. I had picked the wrong direction to lie down. My head was pounding, and I had to be back at my hotel by 6 a.m. to meet up with people from my work. I woke Cindy up, and asked her if she wanted to fool around. She told me I must be fucking kidding. I told her I had to go – and she said, “Well then go!” … so I threw on my clothes, and out the door I went. The hotel was about six miles away, and I was almost there when I realized that I had left my fairly new $700 leather jacket at Cindy’s. I knew that Cindy was really pissed off at me – and I calculated that she would never send me the jacket … so I turned the car around, and drove right back to her house. It was 4:30 a.m., and I was pounding on her front door. She finally swung open the door, and screamed something like, “WHAT THE FUCK DO YOU WANT?” … and I told her I left my jacket inside. She went and retrieved it – and threw it out the door at me. I went back to my hotel, and got an hour’s worth of sleep before getting up for my work day.

My colleague that I was meeting with for breakfast at 6 a.m. knew that I was going out with a live wire the night before. When he saw me, the first thing out of his mouth was something like, “Wow – you look like a train wreck … how did it go last night?” My response was something like, “Not exactly as planned – I believe I was her WORST DATE EVER.” At the end of the day, I started the long drive back to the Los Angeles area … and I rang Cindy. She didn’t (or wouldn’t) answer her phone … so I left her a message that said something like, “Hey – I’m really sorry about last night. I’d really like to make that up to you.” … but I never did hear back from her. I did talk to her some nine months later … I called her at work, and she told me that she had met a really rich local Santa Barbara man, and was engaged. I never tried calling her or heard from her after that ;o)

Okay – so that was my story … what did you think? My take has always been that it is fine to make mistakes, as long as you learn from them and do not repeat them. I discuss this concept at length in the Periodic Re-evaluation subsection of the Develop a Strategy for Midlife Bachelor Success section … all under Midlife Dating Advice. My lessons from this incident were obviously:

1. Don’t drink too much on a date
2. Don’t smoke ever – as it disagrees with me
3. Don’t throw-up on a date
4. If you think you might pass out while you are waiting for your date to take a shower, then don’t lie down!
5. Don’t expect to have sex at 4 a.m. if you’ve previously violated items 1) through 4)
6. Write off whatever personal belongings you left behind during your drunken maneuver

So that’s it – I had to be Cindy’s WORST DATE EVER. If you have ever been someone’s WORST DATE EVER, I’d love to hear about it!

About the author: Gregory Smith is a forty-three year old divorced midlife bachelor who founded midlifebachelor.com - a website dedicated to various midlife issues, especially dating.

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