Dear Emily,

I was only 23 when I got widowed. My husband of two years died suddenly of a massive heart attack at 25. We had no children. I moved on with my life, finished my masters degree, and lived as a single woman for 30 years.

The men I met then were not marriage material. Some thought I was just in need of fun, others were looking for a mother. A year ago, a young guy doing low-level work in the office was assigned to work as one of my research assistants. Soon he was my go-to person, becoming indispensable in this project. He was always respectful and deferential and was never unprofessional or familiar.

I am embarrassed to admit that working together so close this past year year has affected me physically and emotionally, something I haven’t felt for a long time. I miss him when the week is over, and can’t wait to go back to work on Monday. He had a shotgun marriage, but immediately separated from his wife after the birth of their child 10 years ago.

I have not heard any rumor of a male or female being associated with him. He is 21 years younger and working with him day in and day out is becoming an ordeal for me. —EMBARRASSED

Tough, isn’t it, to be shackled by the norms of society? The freedom to express one’s feelings is frowned upon, more so when the age difference is deemed objectionable in the case of an older woman falling for a much younger man, but not between a young woman and a grandfather-ish man. It’s okay to have a sugar daddy, but sugar mommies are judged harshly.

In your ordeal, tread carefully. With a project at hand and surrounded by co-workers who have eyes and ears in the pores of their skin, all set to monitor your nuances, have a benign attitude toward them. Treat them all alike. Joke with one as you would the other, go on outings in groups of two or more, regularly—if only to set the stage and not raise anyone’s hackles later on, should you and this guy be seen together.

It’s truly a bummer that you, a mature woman, cannot go out with whomever you want. But you’re not in a normal setting. You are the boss and he is a subordinate whose feelings for you are as clear as cardboard. It would have been easier had he showed some interest, no matter the differences in your status.

Start a friendship he won’t feel caged in—and see what happens. Go with the flow. Trust that water will seek it’s own path. If it’s meant to be, well… And, don’t be hard too on yourself. You’re only human, after all.

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