Valentine’s Day advice from an official matchmaker

How should new couples mark their first Valentine’s Day?

Valentine’s Day traditionally falls on the man. He definitely should do the traditional flowers, chocolates, dinner. At the six-month mark, I would definitely recommend getting some sort of jewelry. The woman should always do something cute, not necessarily expensive, but sentimental, romantic.

Should Valentine’s Day matter to long-term couples?

They’re the ones who need to consider it more. I’m a big believer in giving a handwritten card every year of all the reasons why he loves her, and she should do the same.

Valentine’s Day can stir up complicated feelings if you’re not in a relationship. What’s your advice for single people?

They might not have a boyfriend or a girlfriend, but they do have a valentine — themselves. They need to love themselves. 

Let’s get practical. What should one wear to a Valentine’s Day date?

Step the bar up. Wear something sexy, fun, romantic. I bought myself a sleeveless pink dress with red hearts all over it. Men, definitely pink shirts, purple shirts, red shirts.

Who pays for dinner?

The man always pays. 

What about venue, an old favorite or something new?

Try something different, because you want to add as much excitement as possible.

What is the best Valentine’s Day gift you have heard of?

The greatest gift is getting engaged.

And the worst?

A vacuum.

Secret Valentine’s Day messages. A good idea or not?

Definitely in high school, in college, in your 20s. When you’re 30 and up, no more games. Now you have to put some sort of plan in motion on how you are going to find love.

One big ‘do’:

Flowers. There is no excuse not to get flowers.

One big ‘don’t’:

Don’t be cheap on Valentine’s Day. It will ruin the relationship.

Remember…

The more you do for your partner, the more they’re going to want to do for you. Treat him or treat her like you want to be treated.

This interview has been edited for length and clarity.