Hot for Boss

Dear Dr. Sadie,

I am in my mid-20s, and I work in a small start-up with a small group of people who are all in their mid-20s to early 30s. We work very long hours. There are even cots in the office, in case we need to sleep there. Everyone is very dedicated, but our social lives have taken a serious hit. 

I have developed the hots for my boss. She's nice, supportive, attractive and intelligent. She's perfect for me. If I had a social life outside of work, I would never consider dating someone from work, but because I'm in the office 80 to 140 hours a week, I really have no other opportunities, and I'm feeling a little lonely.

I am worried that if I ask her out, and she refuses me, it might change the dynamics in the office (which are very good). I am also worried that if we do start dating, it will also change the office. I am also worried that if we start dating, and it doesn't work out, I'll have to leave the company.

What should I do?

- Nervous, but lonely

When I get to be your age, I will date with you, so we can be friends, and we can go to the beach, and we can both get hot dogs and lemonade. You shouldn't ask your boss out.

Until I get to be that age, we can invite you over to our house for dinner. You can have leftovers with us. We had chili last night, and it was good. You can help us know what time it is, and you can help us keep a watch out for bad guys.

If you come over, I'll give you hot dogs and marshmallows in your hot chocolate. You can stay in our guest room.