Dating Isn’t Funny Business

Samantha Rice
6 min readMay 3, 2021

Many years ago I found myself back in the dating scene. The climate and networking tools had changed significantly since my lasting dating endeavors. While separated from my first husband I met my boyfriend of almost four years somewhat accidentally. I was at a bar, smacked him on the bum and handed him my business card. However, I was quite a dysfunctional girlfriend to him and that relationship ended.

So, in our present dating environment (almost three years ago) I found myself learning new networking skills and meeting quite a few new people. I suffer from a bit of co-dependency and haven’t been outside of a relationship for most of my adult life. The separation from “Cliff” was difficult. I convinced myself that I was not impacted by it and immediately posted profiles on a few dating sites.

My first date was a huge disaster. We messaged each other for a week before having lunch. He would send me absurd surveys about my likes and dislikes. This seemed a bit sophomoric to me; however, I was willing to engage in this “get to know you,” banter. Upon seeing one another it was obvious neither of us found the other attractive in person. He ushered me up to the counter to place my order first and pay for it as well. I’m still old school and while I wasn’t fishing for a free lunch, I also appreciate a bit of chivalry. He proceeded to criticize all my words and once the torture ended agreed we would reach out again soon. There was no reaching out again.

An important lesson was learned. Do not under any circumstance commit to anything more than coffee on the first meeting. I proceeded to set up my next date. We met for drinks (although I don’t drink) and had a nice evening. He was nice, funny and relatively sane. We agreed to have dinner the following Sunday.

That Sunday afternoon I left my purse at our weekend place. I needed it for the week but also had my “big date.” I decided I would pose the option to drive to my house, grab my purse and get dinner. This would be a great opportunity to chat and get to know each other. It was also another opportunity for me to flounder through another dating mistake.

He drove and we had a nice conversation on the way to my house. When we arrived he kissed me. Suddenly, I realized this was not a good idea. Not just the kiss but the entire date. I was foolish to think after almost four years with someone I could just move on after a week or two. With that kiss I felt riddled with guilt as if I were cheating on my ex-boyfriend. I wanted this date to end. I was also forty-five minutes away from my car.

I decided to fess up and tell him this isn’t working. Another lesson learned here. Don’t tell someone twenty minutes from your car the date isn’t working. He was kind and took me to my car. Later that evening I received a very long e-mail detailing how awful I was and how I should never be that cruel to someone. I felt miserable. I took down all the dating pages and decided I needed time to heal and enjoy alone time before muddling through dating.

Two weeks passed; I was healed. I put the sites back up and started the dating marathon. One evening I had three dates lined up. They were all coffee dates and I executing them like Kung foo fighting, you know, with expert timing. I noticed one very, very interesting thing about most of my dates though. They were not funny. Nope, they did not possess one little shred of comedy. I spent four years with a hilarious man and date after date after date I didn’t crack a smile. This wasn’t funny business at all. Not funny on a variety of levels.

Making it less funny literally is all the channels of communication. Technology is a critical beast. You must text, instant message, e-mail, etc. and rarely talk on the phone. Hundreds of electronic messages are exchanged before the first meeting. I didn’t have an instant message account, other than Facebook. So, I would use Facebook messenger. Ahh, yet another painful mistake.

I friended one fellow and we chatted all morning. We agreed to meet for coffee. I preferred the local mom and pop coffees shop. I prefer their coffee. He insisted on Starbucks. That coffee is too strong although I agreed. He arrived in July on a sweltering day in long pants, a shirt and a tweed jacket. He iced down his coffee three times. He went on and on about how he facilitates club (bar) promotions and has a profitable resale business. I was dying to end this date. After an hour and a half it finally ended. He rode away on his bicycle. Hello, that is why we had to go to Starbucks. My coffee shop was on the other side of a busy intersection. The Starbucks was closer. This also solved the mystery about why, on the dating site check off list, you had to indicate whether or not you own a car. I found out many eligible bachelors do not own cars.

During our conversation I mentioned I would be driving to my cabin later that day. He, in a rather pitiful way, begged to join me. There was no way he would be joining me. I drove down alone and enjoyed a quite weekend to myself. When I arrived home, I logged into Facebook and this fellow had posted he spent a relaxing weekend meditating at his cabin. Remember, he didn’t own a car. He fabricated the story about meditating. I unfriended him.

The next day he sent me a text message. “So, you don’t want to go out again”? I replied, in a very kind tone, while he was very nice I would like to pursue other opportunities. I received many more texts following my lovely reply. One of which said, “I wouldn’t want to date you either. Your eyes are bug-eyed and you have disgusting man hands. I wouldn’t f*ck you so you can go f*ck yourself with your own dick.” I walked over to a co-worker, asked her if my eyes were buggy and she replied, “No, you just have really big eyes.” I did not reply to this fellow and fortunately, after he released his rage, he made no attempt to contact me again.

It is a damn good thing dating wasn’t my profession. If it was I would have been fired. I decided to just have fun with it and spend more time with my girlfriends. It just so happened on one of these occasions my girlfriend decided to set me up. We arranged to meet at her house and her boyfriend happened to have one of his friends over too. In all honesty I was a bit miffed at her for the set up. I was supposed to be enjoying girl time. However, the friend, Chris, and I hit it off instantly.

We set up a date the following weekend. I am very strict and serious about my rule that my children don’t meet anyone I’m dating until I’m serious about that person. However, this one felt different. We agreed to meet at the cabin with all of our kids. It was the best date of my life. The following week I had to travel for business. I talked to Chris nightly for hours. I am not a huge fan of talking on the phone so clearly this was serious.

I’m rather certain I fell in love with him in the first week. Within a month I knew I wanted to marry him. I took my dating profiles down the first week I met him. Within a year we were engaged and two years later we married. Like many other things in life I found when you stop looking for them, they find you. Chris is the funniest man I know and he completely took the unfunny out of dating.

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Samantha Rice

I'm a mother of four young adults and six fabulous canine furbabies. My career is in Market Research. I am an avid volunteer.