Unless you're going to a "tastings-style" restaurant, Valentine's Day is not to try wine for the first time. If you'd like to order a bottle of wine, learn a few things about wine well in advance. Learn the difference between a red and a white wine; learn the difference between a Chardonnay and a Sauvignon Blanc; know the difference between a rose, a Pinot Noir and a Cabernet.
If you're at a restaurant and would like have wine, consider ordering by a glass. Restaurants usually serve a variety of wines by the glass, enough to compliment any meal.
If you'd like to try a bottle of wine but are intimidated by an extensive wine list, ask the sommelier or server what they would recommend. You can tell them, "I really enjoy a Kendall-Jackson Chardonnay...do you have anything similar?"
Assuming the audience for this is primarily male, you don't have to fully take charge (or ownership) of the wine selection. If you're married, you likely will already know what your spouse likes; if you're on a date, regardless, just ask them--"are you interested in some wine with dinner?" If they say "yes," ask them if there's a type or brand they enjoy. Simple.