Dating & disappointment

“Everybody deserves somebody who makes them look forward to tomorrow.” ~ Orebela Gbenga

One of the biggest obstacles I’ve faced when trying to break back into the dating world hasn’t been my career or my son – it’s timing.

I’ve never had great timing. I can look back over the years and see the pattern. In high school, I wasn’t confident enough and this led to much disappointment because I would talk myself out of even going after a guy I had a crush. I would use excuses as a defense mechanism. Then when those excuses turned out to be even partially true, I used them as a brick to build a wall around myself and my heart. By the time I was to the point where I’d work up the courage to ask the guy out, he was already dating someone.

In college, I tried a different approach. I entered the world of online dating. This ultimately ended in failure after several attempts off and on through the years. I would see a guy who met my list of criteria, and then he wouldn’t live close enough to me, or wasn’t interested. I eventually met my husband through a mutual friend, and after dating for almost a year, we got married and had a son.

I can look back now and see all the ways that marriage wasn’t going to work. We lasted 13 months, and I have a beautiful son. I also learned some valuable lessons about myself. When grieving, you shouldn’t make life altering decisions – like marriage. You also can’t make someone change who they are, no matter how much effort you put into the other person.

I met someone a few years back while I was working as an education/sports reporter for a weekly publication. At that time, he was with his on-again-off-again girlfriend. It didn’t bother me because while I was looking to date, it wasn’t a priority. Then in the fall of 2013, he and his girlfriend called it quits. It was around this same time that I lost my job, so I kept tabs on his situation through a mutual friend, but was more focused on getting another job and exploring different career opportunities presented to me. I explained to this friend that all I really want is just a guy friend I can take it slow with and have it lead to something more in the future. She laughed and said if I get the chance, go after this guy.

When she and I worked together, she had attempted to set us up. However, the timing was never there. He was either dating his girlfriend, or when they broke, I was busy with my son or something else that had cropped up. Then in July, I decided to take a course with my life that put me back in contact with him. We hung out a few more times, and he would flirt with me, so I was just trying to figure out when the right time to ask him out would be.

Long story short, I asked him out a few days ago because I was able to shift some things around in my work schedule. It turns out that he recently got back together with his girlfriend after being single for almost a year. And 56 hours later, the disappointment of it still stings.

Sure, I’ve gone out on dates over this past year with different guys, but I never let them in. I also never entertained the possibility that I might like these guys enough to have a relationship with. I kept my guard up. But not with him.

So, while the disappointment stings, he and I will still have a professional relationship. And I know that I can let my guard down and survive the sting of disappointment. Who knows, maybe he’ll call me for coffee, but in the meantime, I’ll focus on other pursuits.

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