This is sort of related to this thread, but here's my question: What is your experience flirting with people you like, or liked in the past?
I googled some info and came up with three good suggestions: ask for a recommendation on something, ask a favor, and give a sincere compliment.
I know there's a very low probability I could go out on a date with my office crush, and even zero if I didn't try. But I've been trying to strike up a conversation with him haphazardly just to get to know him better and try to make a connection. I know his mom used to work in the same department that we are in now 24 years ago. What little information I have about his hobbies, interests, educational background was from an email our boss sent out. It seems like every time I ask what his plans are or what he does on weekends, his answer is "not much." He reciprocates and asks me about my plans, so I tell him I usually go out shopping or try to catch a movie. Then the conversation doesn't really go anywhere.
I don't want to come off like I'm hitting on him and being too aggressive by asking about his relationship status, which is nobody's business but his own. Yet the very few interactions I've had with him seem forced and superficial. So maybe if I flirt with him in a subtle way, things may be different.
I googled some info and came up with three good suggestions: ask for a recommendation on something, ask a favor, and give a sincere compliment.
I know there's a very low probability I could go out on a date with my office crush, and even zero if I didn't try. But I've been trying to strike up a conversation with him haphazardly just to get to know him better and try to make a connection. I know his mom used to work in the same department that we are in now 24 years ago. What little information I have about his hobbies, interests, educational background was from an email our boss sent out. It seems like every time I ask what his plans are or what he does on weekends, his answer is "not much." He reciprocates and asks me about my plans, so I tell him I usually go out shopping or try to catch a movie. Then the conversation doesn't really go anywhere.
I don't want to come off like I'm hitting on him and being too aggressive by asking about his relationship status, which is nobody's business but his own. Yet the very few interactions I've had with him seem forced and superficial. So maybe if I flirt with him in a subtle way, things may be different.