I guess the answer to the question depends on what he’s saying.
However, the real issue here is about setting appropriate boundaries between your work and your bosses expectations of your job description.
1. Prioritise your own life
You need to ensure that you are not encouraging this behaviour by replying and that means you should be logged off of your work email outside of work. Yes, it’s difficult to do in our ‘always on’ work culture but you have your own life and this should be prioritised over your work.
2. You are not a therapist
You are not your bosses therapist or close friend. Although you are friendly, this doesn’t mean he has a right to invade your privacy with random requests for attention – just because he can.
3. Stop answering non-work related emails
If your boss is sending these emails when you are at work and he is off. Don’t answer them. His emails are not work-related and you should be concentrating on delivering your work tasks. If he asks why you didn’t respond say you didn’t have time as you were busy with your own work.
4. Involve HR if you can’t resolve the problem yourself
If you are uncomfortable with the working relationship as a whole, then you should bring this matter up with HR. Many bosses take advantage of the relationships with their subordinates because the subordinate is in a position where they are scared of losing their job so end up complying with unreasonable behaviour.
5. Set clear boundaries
The other point I would like to make here is that if you do not want your boss to flirt with you. Ensure that you don’t give him the opportunity. Keep the tone of your relationship professional, stay on safe work topics or areas of conversation that you would normally have with the rest of your colleagues.
Some of our most important relationships are forged at work but if you feel uncomfortable about what is going on here. You should make it clear to your boss that work is work and that you won’t be available to engage in anything else. Hopefully, he will get the message.
This post is adapted from a question answered by WorkWisdom on http://www.quora.com