Is he flirting or insulting me on purpose?

[ohso]

I have a friendship with a guy I met, it's fairly new. He jokes around strangely with everybody, so I have a hard time reading him. 

For instance, he asked me out of nowhere how many times I've cheated on my bf. 

I am taken and I was shocked by this question. Why would a guy ask this? What does he think of me then with such assumption?

Is he testing our friendship, like is it real? Or is he trying to sleep with me? 

[ShyViolet]

To me, that sounds like he's interested in you.  He's trying to see if you're willing to cheat on your bf with him.  It also sounds like he's rude.

[schlumpy]

He's tired of waiting. He's been orbiting forever and this is a last gambit on his part to move forward with you. 

[Watercolors]

I know guys like him. Yes, he's definitely trying to sleep with you. You don't have any problems reading him. Do you want to sleep with him?

He's definitely baiting you to see if you'd be willing to cheat on your boyfriend with him, b/c he's sexually attracted to you. He thinks if he acts aggressive towards you like that, he'll convince you to cheat on your boyfriend with him. You need to shut him down, by telling him that you're not interested in him. Unless you are, then that's a whole new thread.

[Wiseman2]

4 hours ago, ohso said:

For instance, he asked me out of nowhere how many times I've cheated on my bf. 

Was he drunk or just being a jerk? Hopefully you don't have a crush on this guy. Pull back and hang out less.

[d0nnivain]

He's flirting by insulting you. 

The correct response is something along the lines of 

I don't cheat.  How many times have you cheated?  

then 

I don't like the way your mind works.  Even if I was inclined to cheat, which I'm not, it wouldn't be with you. 

Then you go over & kiss your BF, preferably in from of him.  

[kendahke]

6 hours ago, ohso said:

For instance, he asked me out of nowhere how many times I've cheated on my bf.

That's called "negging":

Quote

Negging (derived from the verb neg, meaning "negative feedback") is an act of emotional manipulation whereby a person makes a deliberate backhanded compliment or otherwise flirtatious remark to another person to undermine their confidence and increase their need of the manipulator's approval.

I don't think he's socially awkward, I think he has no respect for women. That's not a question to ask someone who has never given you a reason to ask that question. Quite frankly, that's something that you get your purse and walk out and leave him where he stands... and block him before you start the engine/close the door for the Uber ride home.

[smackie9]

No I would have said you are disgusting, now go away.

Why he said that? because he wants you to cheat with him. He's lookin for some action from you. And with a question like that, he has no moral standing whatsoever.

[Watercolors]

9 minutes ago, kendahke said:

That's called "negging":

I don't think he's socially awkward, I think he has no respect for women. That's not a question to ask someone who has never given you a reason to ask that question. Quite frankly, that's something that you get your purse and walk out and leave him where he stands... and block him before you start the engine/close the door for the Uber ride home.

Negging is exactly what this guy is doing. I forgot that's what it's called. But negging is the tactic he's using on you OP. Walk away from this guy. He's 100% bad news for you in every way, shape, and form.

[DarrenB]

7 hours ago, ohso said:

Why would a guy ask this?

To see with what he can potentially get away with if you were to proceed in such sexual/physical escapades with him.

7 hours ago, ohso said:

I have a friendship with a guy I met, it's fairly new.

This isn't a friendship, it's a scheme to get what he wants from you.

[Mystery4u]

He clearly has no respect for women and is only thinking about one thing.

You are taken so why does it even matter? You don't need any new guy friends like this.

Ignore/block/delete etc.