Last Saturday I broke all my previous dating records and went out with my oldest guy yet! The Old Man was 43 so that makes him 11 years my senior. People have been telling me for years to “date older”. As if once guys hit a certain age, they magically aren’t asshole douche hats anymore and thus all my problems will be solved! I have never subscribed to this notion. And when I started thinking about it more, all the people telling me to date older had all married or were dating people barely a year or two older than them. So practice what you preach, people! But, I still wanted to know what going on a date with an older man would be like so when The Old Man messaged me a few weeks ago I took the bait and agreed to a Saturday night date.
The Old Man’s age was apparent early on. He used somewhat archaic dating phrases like “let’s paint the town red” and “come hang out and let’s have an evening!”. Once we traded numbers, the first text I got from him was written like a letter and he signed it. Like – “Can’t wait to see you on Saturday. Signed, The Old Man”. But I was willing to give it a shot. If anything older men at least have money and probably have the chivalry stuff down and really nothing makes a date better than a good dash of chivalry!
I was happy to find that The Old Man had planned our whole date – how refreshing! Someone who knows how to date. So Saturday night I rolled up to the bar where we were having pre-dinner drinks at and was relieved to find that The Old Man didn’t look too too old. If I had to guess, I would put him at late 30s. He still had all his hair and was a pretty snappy dresser. We had two cocktails and chatted about random stuff. He was a pretty good conversationalist though I started to see some wiffs of arrogance which will come into play later. I also learned he did not like any condiments! Weird? We had been talking about onion rings and I sort of wondered out loud what the correct condiment for onion rings is. He shared that he hated ketchup and then I asked him about all condiments and he was blah about all those! Mustard? No. Mayonnaise? No. Relish? No. Man, what a dry life he must lead!
Next, we went to a restaurant for dinner next door. Overall conversation was good but I continued to learn about his picky diet and that really gave me pause. Lately I have been on dates with guys with seriously weird diets! I can’t totally judge. I have a food allergy so my diet is a bit limited but it’s not by choice and if eating gluten didn’t give me the shits for three days I would eat it with abandonment! But what is with these dudes? The Old Man claimed to not really like food and was content eating a dry chicken breast every night for dinner unless he was out to eat at restaurant where he would splurge as he did that night where he had a plain cheeseburger. Really living it up! I don’t know if he used to be fat or just being older he really has to watch his waist line but as a real foodie it just blows my mind when other people don’t like food as much as I do!
Food can be a big foundation of lots of relationship. Half of dates revolve around eating and drinking! So to be with someone who was so picky and had no real interest in food? Ehhhhh. We ended up getting dessert which ended up being this wicked delicious banana, pb, chocolate, and marshmallow layer thing and I only suggested we order it thinking we’d share it. One dessert, two spoons! But he wouldn’t eat even one tiny spoonful! He claimed he was soooo full and couldn’t stomach it. Or more likely he was worried about the carbs! So I proceeded to eat 3/4 of the dessert solo. Carbs schmarbs.
During dinner and then post dinner, as we grabbed a few more drinks at another bar, I began to feel that The Old Man was really just an arrogant jerk. On the way to our post dinner bar, he basically lectured to our cab driver about how he really should switch to being an Uber driver. I don’t know if it was his tone or what but what started as conversation turned into almost an argument between him and this random cab driver. My date being stubborn and sort of rude and the cab driver just trying to defend the fact that he didn’t want to drive for Uber. Once we got to the bar he did the same thing to me. Instead of listening to what I had to say, he would counteract and refute things I was saying. It was infuriating! His attitude just came across as oh, you obviously don’t know what you’re talking about. You’re too young to understand, etc. He was also obsessed with pointing out young people around us! He noticed a somewhat young looking bar back at our first bar and he had to say “Wow, that guy looks 12!”. The diners next to us at dinner “Those kids are probably 21!”. Why did he care? Insecure that he was an older man?
I think The Old Man could tell I was getting a little bit ruffled by his weird conversational ways. I think he knew he was like that but being The Old Man was also probably set in his ways and just was looking for some dim girl to think he was like the smartest person in the world and not question anything he ever said. The Old Man did pay for all our drinks and dinner that night and paid for my Uber home so I will give him that. I gave him a small kiss when he put me in the cab and then texted him when I got home to thank him – not necessarily for the good time – but more for paying for everything. He replied that night but I have heard nothing from him since so I think we can safely say not a match. Thank god!
Will I continue to try to date older men? The verdict is still out. Age is only a number but sometimes it does create a huge chasm between people, especially if it’s something that one person is clearly insecure on.
The Cat Lady 