Tailor & Barber's Guide to Nailing Valentine's Day

I know most of my readers are straight men, but I do have readers who are gay, straight, men, women, etc. I’m writing this piece from the point of view of a straight man who has dated women and is married to a woman, but it can be applied to anyone. Maybe I shouldn’t have to state this, but I didn’t want to offend anyone. Valentine’s Day, and love for that matter, is for everyone.

I’m probably already behind on this post. The time to plan for Valentine’s Day is now. Really, the time to plan was probably a week or two ago, but here we are. I remember, working in the restaurant world, getting calls on January 2nd for Valentine’s Day reservations. Some people are just on top go it. Anyway, I just wanted to hit a few topics about this holiday and weigh in.


I love steak. I used to run a steakhouse. If I faced a firing squad tomorrow, my last meal tonight would be a 30-ounce, dry aged, USDA Prime ribeye, medium-rare. But on Valentine’s Day, I suggest embracing the pescatarian lifestyle. Hopefully, if things go well after dinner, there’s going to be some romance involved. Do you really want that 16-ounce NY strip and garlic mashed potatoes weighing you down? Probably not. I suggest going with some lighter fare. Some oysters, a nice Dover Sole, shrimp cocktail. Just be sure to avoid the live Maine lobster. Too messy.

Opentable is a great way to make sure you have a reservation.


I think personal gifts deliver much more impact and have much more meaning than something you pick up at the last minute from some random table display in a department store. The custom jewelry from Auburn Jewelry makes a great, original gift. Gifts don’t need to cost a fortune, either. Thought and personalization should trump cost every day. And if it doesn’t, you may want to reconsider your relationship.

I would recommend skipping the lingerie and chocolate; just for Valentine’s Day. Those make great “I was just thinking of you” gifts, but they’re a little cliché for V-Day. Of course sending flowers is always encouraged.

Night Out

Whatever activity you think sounds great, don’t do it. Schedule an activity she wants. Maybe it’s a movie. Maybe a play at the theater. Maybe there’s a new exhibit at an art gallery she mentioned. Whatever is it, make sure it’s something she wants to do, not you. Even if you have no interest at all, pay attention so you can have a serious and engaging discussion afterwards. No physical gift will be able to compete with your time and attention.

At the end of the day, you know your date best. If she loves steak, choose a steakhouse. If she craves chocolate, get the best chocolate you can find. If she wants to go to Monster JAM, get her tickets to the next upcoming live event in your area. Whatever you decide to do, have fun!


Tailor & Barber