My boss made an inappropriate and offensive comment towards me

My boss has a habit of making inappropriate comments and he stays quite late every day after work (until 8pm) where he will email me non work stuff, he even suggests we go for lunch when his boss isn't around. We do get on well especially when we work in a office together. Today he asked what my greatest fear is. I was thinking and he said is my fear of being a spinster? I ignored his comments as I hate confrontation and he goes he will tell me his fear which is being poor and I told him if he would like to hear my fear he goes go on and I said having to work with him for the next few years and he laughed and said how he didn't expect that and proceeded to tell someone on a teams call what I said to him. I only made that comment out of spite because of what he said first. I just needed to vent about this.

do you feel safe

No if he keeps making personal comments and I have to work with him in the same office. His manager loves him though.

Report him

My boss has a habit of making inappropriate comments and he stays quite late every day after work (until 8pm) where he will email me non work stuff, he even suggests we go for lunch when his boss isn't around. We do get on well especially when we work in a office together. Today he asked what my greatest fear is. I was thinking and he said is my fear of being a spinster? I ignored his comments as I hate confrontation and he goes he will tell me his fear which is being poor and I told him if he would like to hear my fear he goes go on and I said having to work with him for the next few years and he laughed and said how he didn't expect that and proceeded to tell someone on a teams call what I said to him. I only made that comment out of spite because of what he said first. I just needed to vent about this.

Report him

Before reporting just tell him you feel uncomfortable. I doubt it will help, but if he is a decent guy and just like to fool around he may get that and stop.

The trouble with telling him to back off is that there is the distinct possibility that you will make him into an enemy. With him being your boss, he could make your life difficult in all sorts of underhanded ways. EG writing your performance reviews in a completely biased and unfair way. Or giving promotions to less deserving members of staff than you. Or assigning you the worst tasks more often than other members of your team. Talking badly about you behind your back to poison the other members of staff against you.
The trouble with going straight to your bosses boss is that they may be pally pally, and may stick together against you.
The trouble with going to HR is that they may be pally with your boss, or may refer it to your bosses boss. And HR or your bosses boss may tell your boss about it - which comes back to the enemy issue.
The trouble with doing nothing is that his behaviour may escalate. And he may become your enemy, simply because you didn't accept his advances.
The trouble with going to work for another department or company, is in finding and landing a job that's as good as or better than the one you're doing now.
Sometimes life puts you in situations where it's a case of taking the least worse option.
You won't know for sure which is the least worse option. As it all depends on the exact nature of the people you're with, as well as the relationship between your boss and his boss and HR, as well as the job market for you as well as some luck.
Use your judgement and take a punt on a line of action.
BTW, keep a copy of all written communication between you and your boss. And maybe think about secretly recording conversations with him. You don't want to get into a his word against yours situation.
This will be a stressful time for you, with it being likely to affect how well you sleep at night. Feel free to go to your GP with an open and honest description of how you're being affected. Whilst also at the same time, taking sensible measures to mitigate the stress and anxiety.

...We do get on well especially when we work in a office together...

Speaking as a manager in a large organisation, this is not something you should have to confront him about. You should go to HR.
That’s he’s emailing you stuff in addition to making comments you feel uncomfortable with means you have documentary evidence. Keep copies of those emails.

It is possible to get the tone as absolutely perfect as the tone can be, and still make an enemy of the boss.
It's also possible to get the tone totally wrong and to not make an enemy of the boss.
The biggest variable in this is not the tone of telling him to back off. It's the boss.
Making this a judgement call for Chikane, as to which path to go down.
A judgement call where there's no certainty as to how things will pan out. Because, for example, the boss may have given the impression that he'd be fine about being told to back off, when the reality is that he'd become her secret enemy, with him being in a position of some power.
Or he may have given the impression that he'd take any rebuffs badly, but the reality might be that he'd be fine about it all.
Or he may be entirely predictable as to how he'd react.
It is possible that the least worst route would be a combination:
Have a word privately with the boss, aiming to get the tone right.
The same day, inform HR or the bosses boss. Or report it to them at a later date, depending how things pan out.
Start looking for alternative employment today.
With this particular combination, it would make sense to tell HR / the bosses boss, to keep the information in the strictest confidence and to take no actual action short of dismissing the boss. You'd tell them that you've discussed it directly with the boss and hope that that will be an end to the matter. And that you're merely informing them in event of sour grapes behaviour from the boss, such as a completely biased unfair annual performance review from him, which they should look out for. And that you're informing them so that they can look out for him behaving like this to other employees or clients. Some of whom may not be as confident as you in speaking directly to this boss about it.
Or say nothing to anybody at work about this situation. Start looking for a job elsewhere today. If and when the notice is handed in, be fully honest about all the reasons for leaving: "Better pay, more senior position elsewhere, as well as the conduct of my boss here, which I'd be happy to go into in as much detail as you want..."
When it comes to no-one liking a snitch. The person being snitched on, is likely to hate the snitch. HR and the bosses boss will love snitches if they're good at their jobs. The trouble is. that's a fairly big IF for the bosses boss. As workplaces are full of poor to mediocre managers.

My boss has a habit of making inappropriate comments and he stays quite late every day after work (until 8pm) where he will email me non work stuff, he even suggests we go for lunch when his boss isn't around. We do get on well especially when we work in a office together. Today he asked what my greatest fear is. I was thinking and he said is my fear of being a spinster? I ignored his comments as I hate confrontation and he goes he will tell me his fear which is being poor and I told him if he would like to hear my fear he goes go on and I said having to work with him for the next few years and he laughed and said how he didn't expect that and proceeded to tell someone on a teams call what I said to him. I only made that comment out of spite because of what he said first. I just needed to vent about this.