Hey guys 24-year-old man here,

I'm a shitty texter, at least lately. I have no problems getting numbers or approaching but I have literally no idea what to talk about. Pretty boring conversationalist. I'm pretty good with intellectual topics but when it comes to flirting through text, being naughty/ forward, escalation, etc II suck. So I need tips. Here's my latest adventure:

Got a number from a girl at university and we also fixed a date for next week. Met her at a coffee shop. But I'm drawing a blank on what i should text her in the interlude. I want to strike while the iron is hot. So I need to text her to: get to know her better while not making it sound like an interview, Give off the impression I'm a fun person, gradually escalate to flirty/ naughty texts, etc. Some of my friends are naturally good at it. So does anyone have any links to websites or text logs that could help me out?

Bonus question: Got another number from a girl in my class. We share two courses together and she seems to be actively conversing/enjoying. I don't know if she's into me or not, I just met her today. How long to wait before asking her out? And what to avoid so things won't be awkward if it doesn't work out?