I say it here all the time, and I will say it again. ONLINE PICKUP AND LIVE PICKUP ARE NOT THE SAME.
A lot of the DHV, cocky/funny etc. should have already been done in your profile and/or your opening message. After that the goal of messaging is to GET A DATE. PERIOD. You do not need to go crazy trying to DHV, play mind games, NLP, C/F etc. to get a date. YOU JUST ASK FOR IT.
You write: "Hey, looks like we match. Sounds like you have good taste

Up to anything fun this week?"
When they respond, "Haha thanks, nah nothing too crazy, dinner with some friends"
You reply:
"Cool, yea, I have a low key week as well, maybe doing (some minor DHV activity)... We should meet up sometime. TheFury xxx-xxx-xxxx"
Yes, transition that abrutly. Yes, its ok on the second message (maybe if you are really not comfortable doing this so far and simply refuse to believe me this is what you should do, ask some dumb question to talk about for another message and then ask em out)
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