That actual wince makes her lift her eyebrows and smile a little. It's her natural reaction when she feels a little bad for someone.

"Not what you were expecting huh?" It's okay. Derek seems so ... fit that part of her never expected them to actually share hobbies. Just like how Felicity doesn't expect anyone to actually be that interested in her.

"Let me guess. You like ... hiking and running and ... going to the gym?" By the end, Felicity's practically listing a bunch reasons why she thinks he wouldn't be interested.

As for the technology though, Felicity grins. "Listen. If the technology is hard to use, most of the time it's not your fault. There are whole fields dedicated to making things like phones more intuitive to use. And it makes a difference if you did or didn't grow up with it."