A Man's Guide to Overcoming the St. Valentine's Day Anxieties

For centuries, Christians have celebrated St. Valentine’s Day to honor the martyrs of the third-century saint(s) named Valentine (there were more than one). Stories and legends took hold over the centuries until this day became synonymous with love and romance. In today’s Western culture, Valentine’s Day is a highly commercialized event promoted through ads, articles, and a modern gift-giving tradition.

Before we recover from all the Christmas gift-giving (and credit card bills), here comes Cupid!

February 14th is big business! Hallmark started mass-producing Valentine’s Day cards in 1916. Today, it is a $20 billion industry with 150 million cards exchanged. It is also the most popular day of the year to purchase fresh flowers — which explains the outrageous cost of a dozen red roses the second week of February.

Depending on where you are in a relationship, this yearly salute to Cupid may require more than just a card to convey your heartfelt affection for your beloved.

Through personal experience, I have heard and confirmed that the romantic mood is always enhanced when accompanied by chocolate, flowers, or stones that sparkle. However, during the dating season, especially early in the relationship, you may want to consider a good old-fashioned dinner date on St. Valentine’s Day.

Some may consider a dinner date on St. Valentine’s Day as an expected, if not mandatory, event for anyone seeking to grow a romantic relationship. If your relationship is already strong, you may consider what my wife and I do during this season of hearts on fire — we celebrate a V-Day dinner on either the night before or after February 14th.  Those dates are rarely crowded. But let me be clear: any such decision should be mutually agreed upon. And by no means does that practical option negate the need for the aforementioned chocolate, flowers, or stones that sparkle.

Regardless of when you celebrate your relationship with your beloved, seize the moment, be a romantic, and ask her directly about a date during this Festival Day of Love.  

For all of you romantically challenged gentlemen who struggle to navigate the minefield of expectations that accompanies every February 14th, you may discover a certain amount of anxiety accompanying a dinner date on the most romantic day of the year. After all, every February 14th is an opportunity to put those devoted, passionate feelings into words and communicate how you feel about the most important woman in your life. Unfortunately, we men have a well-deserved reputation for being unable to express their feelings.

So, for you clueless Knights of Woo, here are a few suggestions for how a conversation can go when you are finally seated, enjoying your drink, and staring at each other wondering — what do I say now?

Here are 14 questions to spur the conversation and fill the evening with fascinating discussions and avoid those awkward quiet moments.

Q1:  What do you remember about the first time we met?

Q2: What about our first date made you want to have a second one?

Q3: What has been your favorite date of ours?

Q4: What’s the biggest surprise that you experienced in our dating so far?

Q5: When was the last time I made you smile?

Q6: What role should faith play in our relationship?

Q7: What book has had the greatest impact on your life?

Q8: How would you describe yourself in just three words?

Q9:  How would you describe me in just three words?

Q10: What does success mean to you?

Q11: In what ways do you think we’ve grown as a couple since we first started dating?

Q12: In what ways do you feel like you’ve grown as an individual since we first started dating?

Q13: What’s something you admire about me?

Q14:  How can we make our relationship stronger?

Once you start this Q&A, be prepared. Your date will inevitably turn the questions around and ask you to answer them, too. Luckily for you, you have time to formulate an answer well in advance of the date.

This list of questions is not some magic or fixed list. Your discussion may take you down different paths. Enjoy the conversation. Be focused on listening rather than what question to ask next. By giving your date focused attention, you may generate more questions based on her answers. Go with the flow.

Let’s be realistic. You do not want your romantic adventures to depend solely on the accuracy of a cute winged cherub with a bow and arrow on the once-a-year 14th of every February. So, why not consider celebrating Valentine’s Day every month — unofficially, of course. One month, give her flowers for no other reason than to say “I Love You.”  Next month, send her another greeting card to express your affection. The following month, surprise her with a gift. 

Every Valentine’s Day has certain expectations, so you had better meet or exceed those expectations if you want Cupid’s arrow to hit its mark. By allowing your inner romantic to flourish, Cupid can stay busy all year with surprises that come when she least expects it. Learn to communicate your affections in words (and deeds), and every day can be St. Valentine’s Day — for both of you!

Besides, it’s job security for Cupid.