It could be your first date, lunch with the boss or new in-laws. Either way you are really hoping to impress and making an informed choice when the wine list arrives to help earn you some extra kudos.
Then you are handed a tome the size of an encyclopedia, or, more popular these days, a digital version with a drop-down menu, and you freeze.
There's an index loaded with grape names you have never heard of and regions you can't pronounce.
Suddenly lunch or dinner has become an academic exercise and not a pleasant experience.
Even if the restaurant has a less voluminous wine list, it can still be intimidating to decide what to drink.
Some restaurants will suggest wine pairings for each dish, perhaps this is an option to follow if you're feeling less than confident.
While simple math will show you that ordering a bottle can be a much better deal than by-the-glass options, the stress of paging through a menu, talking with a sommelier, and tasting the wine can be enough to make you throw up your hands in defeat and order beer.
Don't despair. There are some tried and true ways to negotiate a wine list, make that ideal choice and get away with your wallet intact. It's possible to decode a wine list and get exactly what you wanted.
So yes, ordering a bottle makes sense. You get to relax with the wine instead of thinking about whether to order another glass and then the server pours for you.
(If you order a bottle of wine anywhere, the wait person should be on hand to top up your glass).
Ordering a bottle of wine also ensures the wine has stayed fresh and was not opened a few days earlier for someone with the same taste as you.
However, if this is a quick lunch date for two, wine by the glass is the best option and then you are able to each choose a wine you will like.
Most wine lists are organised in three ways.
Region or country of origin, the varietal (grape) and the style (red, white, sparkling or maybe even sweet or dry).
The format can vary, but generally includes: producer, name of the wine, region, vintage followed by a glass or bottle option and price.
If you don't know much about the thousands of grape varieties out there, a major hack is knowing that you're essentially looking at a spectrum of lighter-bodied wines to fuller-bodied.
Gamay and pinot noir before merlots, before cabernet sauvignon and shiraz. Riesling before sauvignon blanc and oaked chardonnay.
So it does help to go into this battle knowing what you are in the mood to eat/drink.
Sommelier Ben Shepherd of Bowral's Bistro Sociale says wine lists have been evolving over the past 10 years, but it remains important that it is written in a style in keeping with the restaurant that it serves.
"Always ask staff what wine they would recommend, but have some guidelines to give about what you like and don't," he says.
"Don't be afraid to tell them what your price range is and don't be intimidated by big wine lists, or unknown, unfamiliar wines.
"The staff are there to help and guide you. You are paying for them to be there, so use them.
"The old adage that the second cheapest wine on a list is the best value is simply an old wives tale. It is true that the cheapest is probably not the best value."
Don't choose what you are familiar with.
When you go to a restaurant, you are generally going to have food that you can't cook yourself (or as good as the chef can), so choose a wine that you can't buy at the bottle shop.
But be clear with what you have in mind, as much as possible.
"Know what boundaries you have on price and communicate that range," Shepherd says.
"Once we know what you'd like to spend, we can narrow down the options and help you find something within that range."
Most sommeliers want to be involved in your meal. To them, the wine is just as important as the food. Follow their lead and you might be quite surprised.