Professional Friendships vs. THAT Guy

Where’s the line?

Specifically, where’s the line when it comes to your personal and professional relationships with other people? Can you make personal friends in a professional setting or should you keep the two firmly separate?

I have a good friend at my office. I helped plan her wedding and even threw her bachelorette party. The party was a damn good night!

There should be nothing wrong with friends in the workplace!!

The women at my company constantly exchange new family pictures or briefly talk about our weekends. We’re all friendly and cordial, but there is a professional line. No one is showing up at each other’s doors uninvited.

But then this happened....

Our janitor came to my indoor soccer game last night. Seriously. This man, though he owns his own company and is obviously successful, can best be described as “creepy.” While I was working late and he was cleaning up, he started asking about soccer and the next thing I knew I had told him where the indoor place was. I honestly thought that he was interested in joining a team himself or something of that sort.

Stupid on my part, I know. And naïve.

So now what? Should I be concerned that this 60-year-old creepster (who has also confessed that he wants to ask out my boss… and he’s married!) is a problem or is this just a one-time experience?

I’ve been asking around and these are the responses I’ve received:

1. It’s my fault for speaking with him about any aspect my personal life in the first place. This is obviously an untrustworthy man looking for information.
     - They’re right.

2. I should inform my boss that he came to the game, uninvited, and make sure that this doesn’t happen again.
     - But, I’m no longer playing on Tuesday nights for a while—is it worth getting my boss involved? I feel like this whole situation was preventable if I had paid more attention.

3. Make sure that I don’t work late when he’s supposed to clean (on Tuesday and Saturday nights). And, especially, don’t be here alone.
     - Yes, this all makes sense, but doesn’t it seem a little drastic? He’s not a stalker… yet.

Is all this worry and hooplah necessary? Even on my own part? It’s all creepy and slightly disconcerting, yes, but I made the mistake of giving him even the slightest amount of information. Besides, I don’t feel like his actions are specifically geared towards me. He’s just THAT guy.

Then again, maybe I should tell my boss… he does a crap-ass job of cleaning as it is.