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Jonathan - Dating a Younger Man

Post date: 2008-12-04

When I returned from my trip alone to Europe, a seasoned wiser woman, I didn’t know what I was going to do with myself. How could I top the adventures I had just experienced? Well, I still didn’t know who I was entirely or what I had to offer in a relationship but in any case, I continued to chat with Mr. Italy and France and also maintained my friendship with my chat buddy the 19-year-old younger man and American, Jon.

I did some casual dating here and there and had some adventures with all sorts of different men; A Karate instructor, a cello player, a pilot and even a lawyer. Each time I learned one new lesson from each man and I got closer to understanding a little about myself and how I was in relationships. I didn’t sleep with any of them but I did have one exclusive FWB (friends with benefits). That, lasted for a while but we mutually ended if after a few months because things got “weird” between us. We had been friends since elementary school but as soon as we got sex involved, it all went awry.

Throughout it all, I maintained my “online” friendship with Jon and turned our Internet chatting into telephone chatting. I loved listening to his Air force stories and was really intrigued about how he was still a Virgin! How could this be? I guess my fascination with his “pure as the untracked snow” image led me into flirting with him on a regular basis.

There was also something “dirty” about him being only 19. Almost 6 years older than him, I felt naughty, I felt bad. What a dirty old pervert!!! I didn’t really know what I was getting myself into, he was “just a baby” in my eyes and it was innocent to just flirt with him on the phone but somehow…I started to develop real feelings for this “baby.”

We exchanged photos, talked on the phone and talked online almost every single day for months and months! I watched him on webcam and we spent countless nights on the phone laughing. Finally, came the day when it was decided he would come to Canada to visit. I wasn’t sure what to expect but when he arrived there was quite a bit of “uncomfortableness” between us. We had practically had an entire relationship over the phone and the computer but now he looked so young to me, I felt guilty and like a total dirty old woman.

Just before Jon arrived I had spent an evening with my ex boyfriend Ewan though. Yes Ewan, the first man I truly gave myself to and whom I thought I was still madly in love with. Once again, I “gave” myself to him and had a beautiful night of lovemaking. It was a moment of weakness he said and left without any mention of him still loving me or us ever getting back together. I could have kicked myself for letting that happen. Of course, this only confused me more and fucked me up beyond belief but I tried to console myself by knowing that soon this American young’un would be arriving to chase the blues away.

So here I was with this American visitor now that I had no idea what do with and a he was a Virgin no less! Feeling rejected by Ewan and confused about my emotions around him, I thought about my whirlwind romances in Europe and my “friends with benefits” relationship with my friend from elementary school. I was in absolutely NO shape to get into a relationship so naturally; I walked right into the young, strong arms of Mr. US Air Force.

Yup, I deflowered the young’un. I took his Virginity and I’m sure he loved every second of it. There was plenty of exciting sex over the next two weeks and the high of being with a new lover overtook us both. It was fun to lie around in bed with a new man. He said the most powerful things to me and made me feel in love. I felt beautiful again, I felt desired. How exciting it was to be with a younger man…how exciting it must have been for him to be with an older woman!

The challenge came however when he announced his feelings of love for ME. We had a magnificent two weeks together while he visited but now that he had gone back to the US and I never got to see him so I didn’t have those “lovey dovey” feelings anymore and the “high” was gone. LOVE? He LOVED me? He told me how he had fallen deeply in love with me and wanted to marry me. I was shocked but at the same time happy in a weird kinda way just because I felt I had finally “won” the love of another man. Maybe I wasn’t so unlovable; maybe I could love another man again. Perhaps Jon was the key to me getting over Ewan once and for all.

We continued our long distance relationship over the phone and the Internet and the next time he visited he arrived with a ring. Not an engagement ring but rather his old school ring that he wanted me to have to remember him by until he could buy me a “proper” ring. I accepted his ring with both happiness and apprehension at the same time. He told me what it would be like to be married to a man in “the force”. It actually seemed kind of exciting. He showed me the sexy uniform he would wear for the wedding if I decided to marry him and I thought about how great he would look in it. A man in uniform isn’t that what all women loved????

Jon really knew how to take care of me. He was smart, loving, kind and very generous. He was an attentive lover and treated me like a queen. Whenever he came down to visit, he cooked, cleaned and was great with my family. Jon really was a good catch and I think it was around that time I finally realized that I was never going to get back together with Ewan. Everyone else really seemed to like Jon. There was no reason for me to still be hung up on my ex; it was time to move on indefinitely. But how? I finally thought to myself that maybe leaving Canada and moving to the US with my American cutie was exactly what I needed. I was tired of pining over Ewan and so…I finally did it and agreed to marry Jon.

Jon was thrilled and excited and I even received a call from his mother congratulating us. I started looking at wedding gowns and making plans half-heartedly. I thought about Ewan a lot; I thought about the men in Europe and sometimes I cried at night at what my future was going to be like. I cried because I would be leaving home. I cried because I wasn’t in love with my future husband and I cried because I was running away from my feelings for my ex boyfriend. I was a wreck. How could I possibly marry a man while still having feelings for another? I did love Jon. I cared about him, I knew he was a good catch and we did have good times together but… was that going to be enough?

In the end, it wasn’t enough and obviously I didn’t marry Jon. I broke it off with him and cried myself to sleep for many nights. He insisted I keep his old school ring and thankfully we both recovered and have maintained contact throughout the years. He was the first man I was ever engaged to and it lasted less than a year. I felt like a failure and cruel bitch for breaking a good man’s heart. What stings most? He always has and always will be willing to talk to me and listen to me whenever we’ve caught each other online. He’ll make a great husband one day, only not to me, some other lucky lady.

LESSON LEARNED: “A good catch” doesn’t necessarily mean a good catch for me. A “rebound” guy is not meant to be your future husband, he is meant to be just that, a “rebound” guy and there is nothing wrong with that. Don’t be a fool and think you can use one guy to get over another, yes it will work but it won’t be the meaningful long-term relationship or marriage you desire. Whenever you first get together with a guy it will be exciting. You might even SWEAR that he is THE ONE and dream of marrying him but hold on there sista, is it the marriage that you are dreaming of? Or is it just the idea of being a bride? Do you want to get into a relationship just to get over a broken heart? Are you looking to marry this guy to run away from something? Marriage is a huge commitment that should not be taken lightly so be clear! Oh and I know you won’t listen to me but please, please try to NOT have sex with your exes.
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