I am a single woman in my mid-30s and have worked for a private company for almost a decade. A few months ago, I took on a new role, working for a partner, “Tom,” who is a few years older than I am. He is notoriously volatile but has always been very nice and professional toward me. A few months ago, Tom and I were working late on a project, and he kissed me. I was shocked. Our interactions had always been strictly professional. We are both single, but I never considered him a dating option because he’s brought a series of different glamorous girlfriends to social events. Tom confessed that he’s liked me for years. We have been seeing each other secretly since then. In private, he is gentle, soft-spoken, calm, and fun—a 180 from his rough and short-tempered work personality. He is also extremely wealthy, which brings with it all the benefits you would expect—travel, luxury gifts, fancy restaurants, etc. Tom recently broached the subject of reporting our relationship to work. We think the other partners would want me to switch out of his group if we report, and that would be a bad move for my career. (I would need to switch companies to keep doing the same type of work.) He told that me it’s up to me but that he’d love not to have to see each other in secret anymore. He’s a partial owner so his career won’t be negatively affected. I like Tom. A lot. But all of my friends think something is fishy—they don’t think it’s normal that he has such vastly different work and private personalities, and they also think it’s unprofessional and sketchy that he pursued someone who reports to him. I guess I have similar reservations, but I am having so much fun with this fairy tale relationship that I am afraid to address them. What do you think?
—Confused ... but Having Fun