I Have A Crush On My Boss. He Is Handsome And Single. Should I Propose To Him?

Firstly you need to be sure about the workplace romance policy and secondly you need to be sure of the fact that if the feelings are mutual in reality and not just from your point of view. If the other party is interested to get into the relationship then things can be worked out collectively. You don't have to go all out and propose him, subtle hints from your side will reveal his interest in you.

From HR point of view this is strictly your personal matter and HR does not have any recommendation on it. What needs to be ensured is that there should be no impact in present or in future on the KRAs that you are expected to deliver as part of your work. In case of a scenario wherein you firm up your relationship then also it should not lead to any conflict of interest. This means that you are required to disclose the status of your relationship to HR because you can no longer be in a direct or indirect reporting relationship with your boss.

Proximity has a weird way of precipitating scenarios that ideally would not have come to fruition. More often than not when you work closely with someone and travel with them, a forced intimacy develops if you are not careful which could also be a possibility in your situation too (please do not construe this as me being judgmental or berating the intensity of your emotions). Workplace romances can have unpleasant repercussions. Hierarchical issues can bring forth an ugly power play in your relationship. Colleagues can get disgruntled or misconstrue your successes as sexual favours. Above all else if you have great conviction about your feelings towards him then be absolutely sure that the feelings are mutual or you will find yourself in an embarrassing situation. In all, honestly, I would still recommend not mixing business and pleasure.