I've written about my work situation on here before... so here is another one...

I work in a small office and privacy is limited. My male boss who is as old as my dad thinks that drives around the block to talk to employees about sensitive issues is appropriate. He emailed me saying he wanted to take a drive with me today. I flat out refused. He is basically a stranger, and I am not getting in a car with him. I told him back in an email that I thought a drive would be unprofessional and inappropriate given I am a young woman and he is my older male superior and anything he had to say to me he could in the office given the professionalism of the staff. He keeps pushing for these secret meetings and I am uncomfortable. Ideas?

If you feel uncomfortable, follow your instincts. It may be that he genuinly wants to talk and not try anything, but even so, this is inappropriate. If he becomes angry at the fact that you do not wish to be alone with him, then that is definitely a red flag. If he respects your concerns, then you may be able to continue work without an issue.

But really, trust your gut. If it gets to be unbearable, look for a new job or ask to be relocated... these are difficult changes but nothing is worth more than your safety and well being

Of course there are issues that deal with records, pay, benefits and other issues that can not be discussed in front of others. So there has to be a private place at work to meet if there is no private area.

My suggestion would be to offer to meet him somewhere public but away from anyone that would care about your discussion. Starbucks, a local restaurant or something similar would be appropriate. That way you can discuss the issues openly but still have the comfort of witnesses.

Tell him you would be happy to step outside the front of the building and discuss the issue while enjoying the fresh air.
Ber