Have you ever made one of your fantasies become a reality? Let me tell you about a time that I did…

Over my holiday break from work this past year, The New Guy and I made a trip down the South Carolina to see The Kid. Naturally I posted photos of the 3 of us together on social media. As expected, pictures of the kids garnered more of a response than anything else I post on social media. Even online acquaintances will come out of the proverbial woodwork to give a “thumbs up” or even. “heart” when it come to kids.

So it’s not surprising when online friends of the female variety post a random comment as well. Typically these comments consist of “nice pic” or “cute kids”. But every now and then, some comments will include some kind of question: a non- rhetorical, open ended question that warrants a responseoften times, these questions can be quickly answered, and one simply moves on. But every once in a while you realize at the question is an opportunity to engage in a conversation. You follow up with them, and you hope that they follow up with you. Before you realize it, she’s writing you and you’re writing her. The next thing you know it, it’s a full-on conversation.

That’s how it started with Boss Lady.

Before I go any further, I have to provide some background: I was what many might consider to be a dork in high school. I was relatively antisocial, I didn’t have a lot of friends, and I spent more time looking at my feet as I walk in the hallways as opposed to the eyes of my friends and girls whom I’d like. I bring up high school because this is where I had my first run in with Boas Lady, although she probably didn’t even know it

Boss Lady is one year my senior; And she was quite literally that beautiful girl that I’d see in the hall every day at school but never had the guts to talk to. She was so far out of my league, that I am not sure her and I were even playing the same sport. She had cool friends, she wore cooler clothes, and she carried her self like she was so comfortable, so laid-back, in every situation. She exuded confidence and sexuality. She was hot and she knew it. She had that smile, that swagger, that air about her that she knew that she was THE hottest girl in the room. I was about as likely of talking to this girl in high school as I was of walking on the moon. Twice.

Fast forward now to more recent times. By the time everybody had already friended all of their real life friends on social media, as well as all of their work contacts, many of us got to a point where we would get “suggested friends”. Sometimes these are not so much people you know as they are people you “know of”. Often times, they are the friend of a mutual friend. Thinking back to my high school, it was just large that even if you didn’t necessarily know a person, you could usually at least connect their face to their name; or the very least you at least heard of them.

Like many of you, I have been guilty in the past of friending some of these people who I didn’t necessarily know. Maybe they were friends of a friend of mine. Maybe I would see them making comments on another friends post and I thought we seem to have a lot in common. And occasionally some of those are just people who you wish that you knew in high school and wanted to get to know better. Boss Lady is the latter.

Through our own version of “Six Degrees of Kevin Bacon” Boss Lady and I have been Facebook friends for several years. Some people tend to lose are used for good luxe as they get older. Others are lucky enough to become better looking, more mature versions of their younger selves. Boss Lady definitely falls into the latter! It’s not as if I made a point to try and talk to her at the time or anything. Becoming Facebook friends with her was fulfilling enough.

Overtime, I noticed she would like one of my profile pics here and there. Mostly it was likes of photos of the boys. And there does seem to be some kind of universal code amongst people that we like pictures of each other‘s children, just because. So again, I didn’t really think a whole lot of it. it was only gratifying in the manner in which we get gratification from the number of likes we receive on our posts. And yes, it’s true, even those of us who like to act like we don’t care about that do like to get a lot of likes on social media.

To bring things back full circle: while I was down in SC with the boys, this past Christmastime, Boss Lady commented in my Facebook post that included photos of me & the boys. Not only did she “like” the post; she also commented on it. in social media, just like in real life, sometimes a comment is simply a comment. Other times it is a conversation starter. This one was the latter, so I decided to respond. New Year’s Eve came up, since we were on vacation that week. We both joked around about how we had no plans for New Year’s Eve. At that point, I decided that I would follow up with her after I was back home. “So how was your NYE?” I asked her in Facebook messenger.

That was three months ago. Since then we’ve seen each other a couple of times for dinner, and we eventually slept together. I don’t know that we have a future together. We have some common interests, like music. Obviously, going to high school together, we have some common experiences from growing up. The truth is, I think we have different approaches to life. She has a daughter in her early twenties, so I know she’s in a different place in life than I am right now. Another big thing is that we have different political views. I don’t mean in the way that we can have friendly discourse in see where the other person is coming from, or even in a way that we would just sit and argue with one another. It’s one of those conversations that, when it comes up, we usually try to steer clear of it.

We still talk every now and then, but not like we did before. I asked her once what happened with us. She said that she thought she was just so used to being alone that she just kind of reverted back to her regular day-to-day tendencies. I can understand that. She’s been single a long time. But I also think that if you like somebody enough – enough, you just start throwing caution to the wind and you just want to see them and talk to them as much as you can.

I have a friend and fellow baseball fan who is originally from Boston. He and I once talked about what it was like there in 2004 when the Red Sox beat the Yankees for the AL pennant, and ultimately went on to win their first World Series in 88 years. He had said that for many Bostonians (himself included) beating the Yankees that year was the real treat. The World Series, he said, was just icing on the proverbial cake. That is how I feel about my experience with Boss Lady.

If her and I never dated again, it wouldn’t break my heart The truth is, there is still an under-sexed, 15-year-old adolescent living inside me; and he is basking in the glory of what 47-year-old Rob accomplished. I don’t feel that I used Boss Lady; nor was that my intent. We never really “broke up“ nor were we ever really an item. You’re still on speaking terms. Sometimes, I worry that maybe I wasn’t “good nothing “in bed, and that’s why things stalled out. But even if that’s the case, I don’t really care.

I literally made one of my adolescent fantasies become a reality, and I became my own hero in the process. How many recovering geeks can say that they’ve done that?