Listen, I'm not the kind of guy whose personality shines trough DM's so well, but...at the same time, this girl is quite shy or she needs time to give me a chance.

Problem is, I don't really know that well how to start a conversation out of the nowhere through a DM. I mean, there is no "flow" to it, and I don't want to make it an "interview" where I'm just asking her questions like "how's it going", "what are your plans", "how was your practice?" etc.

I want to make the conversation interesting, and I will try my hardest and I think it will shine trough if I will go out with her, but until then, I need some fun topics/conversation starters to keep her attention and commence.

Any ideas?