Totally feel ya! Here's some fun ways I've found make it a little less awkward: 1) Even though it may be cheesy, put one of those virtual zoom backgrounds up! It always sparks up some fun conversation to break the ice. A photo of your hometown, something you love, somewhere you'd rather be, just something you can chit-chat about! 2) Have 3-5 go-to questions prepared (even if they're simple like "How was your weekend?" or "What's been your go-to quarantine pastime?") - driving the conversation fills the awkward gaps. 3) Pretend like you're in person! Zoom is actually a lot more intimate than an in-person meeting (since you're sort of in their home) so giving some grace & cracking some cliche Zoom jokes at the beginning always loosens things up for me... "Omg, I am totally feeling the Zoom fatigue! Can you hear me / see me? Are you tired of all this virtual stuff yet?" 4) Worst case scenario (and not the best but we all gotta do what we gotta do in times like this), start with your video off and say you're having some technical issues. Let the convo start there and once you feel a little more comfortable, turn it back on! Honestly, it's a little strange (and exhausting) that our old school phone convos all the sudden turned into full fledge video conferencing but just be yourself & know we're all in the same boat! No one was made to be on Zoom 24/7... I think most of us miss the less-awkward / no-technical-issues coffee meetings, so just lead with the fact that they probably feel the same way!