Girls, would you find this question too straight forward?

So, let's say there's a girl a guy is interested in, and he first wants to find out if she's single, before shooting his shot. Would it be weird to too straight forward if he started to make conversation/small talk, and said something along the lines of "so, how's life, how's the romance going, you seeing anyone?", said in a rather light and playful manner.

I feel like this is a "safer" approach of trying to ask out someone, because if you immediately go in for the kill, the stone cold rejection will just hurt more than it should, and perhaps the girl will also appreciate it if you feel her out first and give her a chance the dismiss the (potential) advances without putting her on the spot.

I have approach/rejection anxiety, so I'm trying to find a strategy that'll work for me, as pathetic as that may sound ;DDD

its good
its not good
Select gender and age to cast your vote:
Girls, would you find this question too straight forward?
Post Opinion