I want to stop being a nerd for a second and take my family somewhere

Many have been and are in the same situation.

I'll be frank, if you're serious about wanting to connect on a deeper level with your family, the place of choice is irrelevant. Check on Google what restaurants within your proximity have great reviews and go from there. Stick to universal meals that everyone can appreciate if you have fussy eaters. The real challenge will be working on your communication skills and have an honest conversation with your family.

If you don't know how you feel, talk to them about it in the way you have done here. "Hey, I feel like I've spent my whole life on the PC and don't actually how I feel. It may sound strange but I want to be able to take you guys out more often and have chats."

Best of luck.