re: Your're going to a chain steak house. Your choices: Longhorn, Outback, or TX Roadhouse

Texas roadhouse and get a medium rare cheeseburger, they were pretty good 10 years ago.

If you want a good steak for the boy, find a good butcher, buy a couple filet, sear them rare in a cast iron skillet and cook for maybe 3-4 minutes at 400 in your oven. Will be better than most restaurants, certainly better than any of the chains.

Also could try this grill-chimney method from Alton Brown. My dad and I do this every summer a few times, would be a fun father-son activity for yall.
https://www.americastestkitchen.com/articles/3473-for-the-ultimate-char-sear-your-steaks-over-your-chimney-starter



But bottom line there are a lot of ways for you to get your son a killer filet without going to a crappy chain. That's part of a father's wisdom - "no steak at all is better than a mediocre chain restaurant steak".