Women associate Valentine’s Day with romance, love and intimacy but for men the occasion evokes more trepidation then anticipation. The challenge of meeting their significant other’s expectations presents a minefield of potential disappointments that can blow up in their faces with any misstep.

Here are five simple guidelines for men to keep in mind when planning their Valentine’s Day. Following these tips will help them cross the minefield unscathed and make the night one to remember for all the right reasons:

1. Keep it Romantic: Many men play it safe by planning the evening around their wife or girlfriend’s favorite restaurant or entertainment venue. Unless the places or activities in question are truly romantic choices, planning your Valentine’s Day around them is a big mistake. She might love karaoke but that doesn’t mean she wants to spend Valentine’s Day listening to intoxicated strangers butcher power ballads.

2. Show thoughtfulness in the gift. The most important aspect of a Valentine’s Day gift is how much thought you put into it. For many women, the amount of thought you invest in the gift represents a barometer of your true feelings for them (even if you don’t consider gifts very meaningful yourself). Last minute purchases are often problematic for this reason, even if the gift itself is great. As a general rule, a small gift that had to be shipped from Timbuktu is better than an elaborate gift from the store across the street.

3. Make it personal One of the best ways to convey thoughtfulness is to personalize as many aspects of the evening as you can. Add touches that are unique to your wife or girlfriend or specific to your relationship. For example, red roses are great but adding an extra rose in her favorite color to the bouquet is even better. Or download her favorite romantic song to your cell phone and play it for her as you hand her the gift.

4. Don’t underestimate the importance of the card. Most men don’t get cards but cards are very important for women both because of the sentiment the card conveys and as a keepsake. The most important words in the card are the ones you write, not the ones Hallmark writes. Signing your name and drawing a heart won’t cut it. Add a romantic sentiment of your own even if just a simple one such as, “Thank you for making this Valentine’s Day truly special”.

5. Be prepared for surprise tests. Yes, Valentine’s Day is February 14 but if at one minute past midnight on the night of the 13th your significant other leans over and says, “It’s officially Valentine’s Day. Wouldn’t it be fun to exchange cards now?” don’t say I didn’t warn you. Such surprise tests are her way of evaluating whether you care enough about her to have invested the thought, time and effort to plan ahead. Have your card ready to go (including your own added sentiment) at least 24 hours before the day itself.

Copyright 2011 Guy Winch

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Guy Winch, Ph.D., is a licensed psychologist, keynote speaker, and author whose books have already been translated into thirteen languages. His most recent book is Emotional First Aid: Practical Strategies for Treating Failure, Rejection, Guilt and Other Everyday Psychological Injuries (Hudson Street Press, 2013). The Squeaky Wheel: Complaining the Right Way to Get Results, Improve Your Relationships and Enhance Self-Esteem (Walker & Company) was published in January 2011. Dr. Winch received his doctorate in clinical psychology from New York University in 1991 and completed a postdoctoral fellowship in family and couples therapy at NYU Medical Center. He has been working with individuals, couples and families in his private practice in Manhattan, since 1992. He is a member of the American Psychological Association. In addition to the Blog on this site, Dr. Winch also writes the popular Squeaky Wheel Blog on Psychology Today.com, and blogs for Huffington Post.