I recently went on a solo road trip (2700 miles), so I was able to practice ordering in a variety of new restaurants.
First, if you’re out, go to places other than what you’re used to. On my trip I avoided all chains (with the lone exception of Culver’s, which we don’t have in my area), so nearly all of the menus were new to me.
There are a few options when ordering. One is to order the dish you are not crazy about, i.e., that is something you might like. And if it’s a dish that that restaurant specializes in, go for it. Like many people, I generally dislike liver and onions, but one of the most memorable dishes I’ve ever had was exactly that, at a place renowned for it.
Try not to order what you make at home, or what you usually get. A million places make hamburgers (and I’ll humbly submit, mine are better than nearly all of them). So no burgers. No spaghetti. No meatloaf, etc. Try oysters, shrimp, and scallops (especially if you’re near the sea, or near a place where they get frequent shipments, i.e., a transportation hub).
The best is to ask the waiter/waitress, and don’t ask “what do you recommend?” First, from what I know of the restaurant business, they often are supposed to recommend certain dishes, often what is selling slowly or which for they have excessive ingredients.
It is recommended that with a doctor don’t ask “What do you think I should do?”. Instead ask “What would you do?” Similarly, ask the wait staff what they like most on the menu, which is different than asking “What do you [i.e., your manager] think I should eat?”
That is also a good approach when going to ethnic restaurants, to avoid being steered toward food that they think people of your (different) ethnicity would like. (I had a bit of an argument with a waitress in a Chinese restaurant, when I ordered pork bellies with Chinese spinach, from the “Chinese” section of the menu, and she tried to dissuade me, insisting on the kung pao chicken, which ironically was the first dish I ever had in a Chinese restaurant, many years earlier. And I quite liked the pork bellies, to her surprise.)
Another of my techniques is the three-finger selection. I splay my hand and drop it onto the menu, and I have to order one of the three dishes my fingers are pointing to.
I also recommend learning your wait staff’s names, and using them. I haven’t worked in that industry, but I’ve read and heard that it is exhausting and literally thankless. Being more personal with them is a great way to connect and converse, and I’ll selfishly admit that it has personal benefits: at an excellent meal on my trip, I talked at length with both the manager and the bartender. On my final bill, they comped me for one beer (Kwak, my favorite beer, and on tap), and dessert (pecan pie made with Gulden Draak, another of my favorite beers).
When eating out, it should be an adventure. After all, that’s one of the main reasons to go out, right?