Some nights call for stepping outside of your usual routine and stepping things up a notch. The occasion will be different for everyone—it could be senior prom, or the night you plan to ask your girlfriend to marry you, or a celebratory dinner in honor of a big raise or promotion, or your 25th wedding anniversary, or a night of debauchery with your fellow singletons—but methods will be the same: a rented town car to pick you up at your home, dinner at an upscale and hard-to-get-into restaurant, and then entertainment of your choosing. Seems simple enough, but you may need a few pointers when it comes to pulling it off well—after all, this isn’t your usual M.O.
Before the night begins, you have to get dressed, and so will whomever is accompanying you. Rather than leave any question about the appropriate attire, you should make mention of it beforehand—not because you think they are incapable of divining it themselves, but as a way to ensure everyone is comfortable. It can feel incredibly awkward to show up for a gathering under- or over-dressed, so save everyone the embarrassment and volunteer some information. A simple, “I’ll be wearing a suit, in case you were wondering,” or “I’ve decided to rent a tuxedo,” is all the direction your guest (or guests) will need.
Once the matter of clothing has been addressed, you’ll need to make sure your transportation is in order. Don’t just assume that making the reservation is all you need to do. Call a day or two in advance to confirm the reservation and the accompanying details are in place. Double-check the hours of your reservation and the cost as well so there are no surprises. (If you can get them to email you a statement, all the better.) If you are celebrating, ask if they provide a bottle of champagne or if it is permitted to bring your own. Policies regarding alcohol vary by company and state, so always inquire about this before making any assumptions. Also, make sure that the driver is being provided with the correct addresses for pickup and your destinations.
For your dinner reservations (you did make reservations, right?), call the day of to confirm with the restaurant. At this time, you should let them know if anyone in your party has any dietary restrictions such as a shellfish or gluten allergy and verify that said restriction can be accommodated. This is not only a courtesy that the restaurant staff will appreciate, it’s considerate of your dining companion(s) as well. It’s better to know if advance if such a thing is not possible, as it will save everyone frustration, disappointment, and awkwardness, and it could save a life.
When selecting your entertainment for the evening, keep in mind exactly whom you are entertaining. If you suspect that whomever will be with you would be offended by something, physically incapable of it, or completely disinterested, choose something else. Don’t take your conservative grandma to see and edgy comedian, and don’t take your liberal girlfriend to a screening of a pro-Tea Party documentary. Use your brain here and all will be well. And when in doubt, ask.
Keep these tips in mind and your special night out is likely to go more smoothly and be enjoyed by all, and you will be able to go home at the end of the night knowing that had everything to do with you.