2. “So… how far have you gone?”
I hate to break this to you, but no matter how close you are to this person, their sex life is none of your business. If they feel like sharing the private, intimate details of their relationship with you, they will do so on their watch.
Not only does saying this cross some serious boundaries, but it also emphasizes the physical part of a relationship too heavily. A real, long-term relationship is about so much more than just the physical stuff — it’s also about the emotional connection. If this person is telling you about their S/O for the first time, don’t resort to questions about sex or attraction. Instead, try asking what this person is like. I mean, think about it: doesn’t it seem ridiculous to ask about their sex life before even knowing what their partner does for a living?
The point here is, don’t cross the line. If they think you need to hear certain information about their relationship, they will tell you.