When a guy asks lots of questions about you?

[Passionfruit03]

Today my crush/coworker and I started talking to each other at work (remote) and it was the first time we’ve talked a lot in a while. He asked me a lot of questions such as “Would you stay in NY permanently?”, “What are your thoughts on what’s happened post pandemic so far?”, “Have you kept in touch with any of your coworkers?”, etc. We also touched on what kind of people we are. He told me he’s shy in real life but his personality type is ambivert depending on who he’s with. We’ve also talked about people we’ve dated in the past, but only because the topic naturally came up. He even shared his long term goal (dream) with me for the first time. Overall it was a nice conversation. Could him asking me all this mean that he’s interested?

[PeteBy]

Of course he is interested. To what level depends on the conversation and how it goes. Based on what you're saying about his personality, he is gauging whether or not it's realistic to pursue something more. That said, the fact he is asking questions and corresponding suggests he likes you.

[Anonymous]

Yes, maybe. I ask women questions to find out whether they have value, and to figure out whether they are worth my time. I'm also an ambivert..