Flip it around--you could also be judging her and thinking she's weird. In 10 years this won't matter. Talk about impersonal stuff first like the weather, Chicago, travelling, the conference, the food.

Try to find topics that you have in common. Talk about the company you work for or the conference you will have attended. Breathing exercises can help when you get nervous. Hope you can relax and be yourself.

Bring a book or go walking around the city. Most people are so busy looking at their phones they don't notice others.

I understand and feel the same way. Feel free to post and we will be there for you!

Have you read any books, decluttered your house, tried a new restaurant, saw any movies or want to see any, gone shopping, vacations ... Try to think of a few topics so if you get too nervous you have something to say. You can always talk about the rain and flooding and ask if they were affected.

And tomorrow I’m going to Chicago (for the weekend) for a work conference with a coworker I barely know. I think I’ll be able to hold my own at the conference itself but I’m so scared I’m going to say something dumb/make her think I’m weird during the downtime (of which there will be a lot). Help!