Lots of questions - weird, bad chit-chat, red flag?

[WhyDelilah18]

I've a close male friend I've been spending a lot of time with recently. He's started asking me a lot of questions about things, some of which have made me feel a little .

Examples from the past week include:

• Why did my last relationship end? Who ended it? What was the conversation like?
• Did I sleep with lots of guys when I was younger?
• What are my relationship 'needs?'
• What was my first boyfriend called?

These all come up in conversations rather than a direct random line of questioning, but still.

I don't think he's got feelings, as has maintained in the past that he hasn't.

Am I being over sensitive? What do you think this is - awkward conversation, a bit odd, or nothing to overthink?

That's really odd. Even if he had feelings for you, those are intrusive questions.
I can confidently say that male friends have never asked me any of those questions.

TBH it sounds a little bit 'stalkery' - like maybe he's found someone online who he thinks is you and is double checking? Or he knows your last boyfriend/partner and is reporting back?

In context they could be fine. Without knowing the dynamics of the friendship though, who knows?

One of my friends and i regularly talk about stuff like this. Another I wouldn't even consider it with.