He called the next day and chatted me up, complimenting me on everything from my dress to my skills with my Wacom tablet. I didn’t even have to ask him many questions. He voluntarily spoke heavily about himself and it took up most of our conversation. He did want to know how old I was and I dodged the question in a ladylike manner. He was 25 with two children and the aspirations of an astronaut. I nearly laughed out loud. He promised his last girlfriend was 35 and that he was used to “older women”. I knew I could never take him seriously, besides his optimistic attitude was exhausting. But I couldn’t pass up the opportunity to get my Cougar wings in going out with a 25 year old. I’d just turned 40 and was looking for a little excitement added to the mix. How cool would it be if one of my 3 was 25 years old? That would put a whole new spin on the plan. I did not realize how my approach would have to be tailored to this new breed of man.
He called nearly every day and finally “set up” a night out, which would begin at the coffee shop where we’d met. By the time that day rolled around, I’d forgotten and he called me the next day and asked if we’d missed a date. I apologized and rebooked the outing. But (I was about to get schooled on going out with children) when that day came up, no confirmation call and when I called the phone was disconnected. Figured. 3 weeks later, he called and apologized and explained his drama filled situation. I blew it off (I was actually no more interested in seeing him as I was in seeing a show at 6 Flags – it was just something you did to pass the time). He spoke at length about some of his motion graphic gigs and a movie he wanted to shoot. I listened, looked up his stuff and let him see some of my work. He again promised we’d get together.
By this time, I’d grown tired of the show and BF#3 and BF#1 kept me plenty occupied. So the morning calls with his extensive discussions about himself and his plans with the random question or two about how to do something thrown in, were getting old. After a couple more weeks, I stopped answering. Imagine my surprise when the phone number changed and I was once again on the morning chat list.
That’s all there was to that, folks. He could never get his situation together and I had smelled BS the second time I’d spoken to him. By this time I was swimming in it every phone call and I racked it up to at least taking my Cougar test – I just didn’t finish.
What I did learn though was that “talking to” a younger man was exhausting. He spoke with an energy that I wasn’t used to. It was uncertain but relentlessly hopeful. He had the energy to keep at something even though it wasn’t working well because he just knew it would change. Though I was young at heart, I’d come to accept certain things and knew to pick my battles. I was eager still and rambunctious but I was pretty clear of my limit and knew when to stop (kind of). It was a bit invigorating to hear his artistic aspirations – it made me think back to my college days when I just knew I could conquer the world. But, I had already made my mark and I was happy with it so he couldn’t talk me into going out on any more limbs. Oh well, good for me.
Here’s where the game changes, ya’ll.
I mentioned at the outset that this was not my life previously. I’d never been homecoming queen or Miss Popular in school. I’d never had a boyfriend every year of my life since I turned 15. I was the bookworm, the weird girl, and quite frankly, the fat ugly chick in a lot of my contemporaries lives. So with this newfound popularity and keeping up the conquest – after this BF#4 situation – I was physically and mentally exhausted.
It took a lot of time to psych myself up to go “shopping”. It took time and effort to dress like I wanted to be approached, to always have something ready to say, to be ready to hold conversations and remember things men said. I was very good at blending into the woodwork and to take a break, I decided to dress in my house clothes/pjs that I’d always dressed in and actually go to my coffee shop to relax and work on some of my personal projects that had fallen by the wayside since I’d begun my quest.

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Please don't be mean but be candid. These are just my experiences - feel free to share (Oh wait, that sounds very support group-ish, ugh!)