Data is Beautiful

My recommendation: don't have (nor expect) conversations. I've been on many dates (high double digits, or more) and I have not once had someone I've met in person resemble what I would have guessed they were like from a dating profile, sometimes for better and sometimes for worse. Attitude, energy, chemistry, ambition, positivity, respect, confidence, grace, social skills, an attractive voice, etc -- none of that is going to come across through text.

The goal should be meeting up in person and figuring it out on the fly. I usually send one message involving something along the lines of "hello , hope you're having a great week", maybe add a detail about their profile that I found genuinely interesting, and then I immediately send a follow up message along the lines of "Text isn't my forte, so I'd love to get together sometime this week and get to know each other over drinks -- unless, of course, you love playing -tag :) Shoot me your number and let's make plans"

If my match isn't comfortable with sharing their number, I propose we meet up for drinks and we can exchange numbers later. If my match objects to meeting so soon (this is maybe 1 in 30 matches or so) I tell them that I understand, but I also let them know (kindly and respectfully) that this probably tells me that we aren't compatible, and then unmatch with them. Everyone else either has no qualms with my approach, or explicitly states that they really appreciated my forwardness.

Spare yourself and your matches the inherently boring small talk, and jump straight to meeting in person. Everyone wins.