I've done this a few times.

It depends on you. I know people who get on really well with asking out of the blue questions like "what's your favourite sandwich?" and "if you could be any tree, what tree would you be?"

I tend to go with pretty standard questions (job, life, etc.) but get playful and flirty with them. Tease a little and ask them why they do what they do and what they enjoy. It's usually pretty positive.

If you can dress well (clean and smart casual and no "costumes", suits or fedoras) & make sure your hygiene is on point (no bad breath = gum, not too much\too little cologne, no BO and hair is in-check) plus hold a conversation, you'll be better than 80% of the guys there.

Last time I went there was a guy in a fedora and another dressed like the man from DelMonte. One of my dates was telling me when we met up after that one guy sat down and pulled out a paper list of his deal-breakers such as she had to get rid of her cat. After that kind of a shit show I looked like James Bond