The great Valentine’s Day debate started brewing over dinner the other night. The question at issue:  Should you or should you not celebrate the holiday with someone with whom you’ve shared three dates or less and, if so, what is appropriate? 

In one corner was my friend Jeffrey, who wanted to buy an engraved iPod for his new flame and was considering cutting his previously planned boys’ weekend short so he could be back in time for a romantic dinner. In the other corner was my friend Kim, who was in a similar predicament, only she feared that any demands would stifle and scare off her new man. As for the engraved iPod, all parties quickly agreed that a gift of this nature was too over the top for date number three. 

No matter how you look at it, what one does or doesn’t do on February 14^th can be a deal breaker when you’ve just started dating someone new. And though many people may make little noise about it or downplay the significance of this Hallmark holiday, as Jeffrey and Kim demonstrated, women and men often have a secret hope that something special or spontaneous will happen to them. 

The back and forth that goes on between your head and your heart pre-Valentine’s Day can be like a never-ending ping-pong match. So here are some helpful pointers you may want to consider:     

Acknowledge the Hot Pink Elephant: Failure to recognize the holiday may send the wrong impression to someone special. If you already have plans for the day, you certainly need not change them unless you want to. Don’t simply ignore the occasion as doing so may cause that new special someone to wonder about your intentions and whereabouts. Instead, be forthright about your quandary and suggest or plan a rain check.

Don’t Get Too Caught Up with Cupid: It’s easy to get wrapped up in hearts and candlelight dinners, but not everyone does it. After all, Valentine’s Day is not a Jewish holiday and the person you are newly dating may not celebrate or ascribe significance to it. According to Jewish custom, Tu Be’Av (the fifteenth day of the month Av) has become the holiday of love, so you may just want to save the festivities for a later, more meaningful date.

Be Tasteful, Not Tacky: While a gag gift of edible underwear may be your idea of a romantic joke, there are certain gifts that can come across as offensive and inappropriate when you hardly know the recipient. Items like slinky lingerie or engraved gadgets may seem romantic but can send off a “too much, too soon” message, particularly in the embryonic stages of dating. Though flowers, chocolates and candy may seem trite and cliché, they are a sweet gesture that sends the right impression.

Finally, while it’s hard to keep expectations at bay, it’s important that you are realistic in what you wish for. If you trust your heart with some controlled moderation, chances are you will be doing the right thing for Valentine’s Day. Here’s to finding love in 2010!