Reinventing Romance: Single on Valentine's Day

Single women dreading Valentine’s Day: you don’t need a date to celebrate, says over 40 dating expert Sherry Amatenstein

By Sherry Amatenstein, MSW

Valentine’s Day Ideas for SinglesQ. It’s so embarrassing to admit this considering I’m 44, but I still hate Valentine’s Day. And yes, I’m also not a fan of New Year’s Eve but somehow the holiday geared for lovers — commercial as it is — gets me every time. I know I’m a bright, attractive, successful woman but not having a February 14th date makes me feel like such a loser. Shouldn’t I have gotten over it by now? — MaryA. Those shoulds should come with a warning label. Intellectually you’re aware that you are a successful, attractive person whether or not the 14th is a day of wine and roses. But you’re dealing with a potentially ego-annihilating combo of pressure that is both cultural (i.e., think Hallmark, Hollywood) and familial. You’re of a generation that no matter how proud your parents were of your academic achievements, it’s possible that subconsciously they put slightly more emphasis on romantic goals for their precious daughter. For me, decades later there’s still a sting when I remember not receiving as many crayoned Valentine’s Day tributes as other girls in our second-grade card exchange.To blame yourself for occasionally allowing this early conditioning and inescapable seasonal hearts and floral displays to waylay you is counterproductive. However, while wallowing is masochistically fulfilling and less fattening than the chocolates you are not receiving, done to excess it carries the weight of an emotional burqa. Have a brief pity party, then become pro-active. Plan for the day. As in celebrate the love you do have and the love you have to give.Debra Benton recalls, "My best Valentine’s Day as a single woman happened at age 40: I kept busy giving cards, flowers, and candy to my mom’s friends who’d lost their husbands, to women I didn’t know in a nursing home, and to women living on the street. I even gave some item to homeless men to give their gals that day." The now married 54-year-old Livermore, Colorado, business consultant adds, "The many ‘Bless you’s I received more than made up for the lack of ‘I love you’s from a man."Other suggestions that have made the dreaded V-Day victorious for a myriad of single women range from the libidinous (i.e., sampling aromatherapy oils, eating caviar, belly dancing) to the slightly rebellious (i.e., host an anti-Valentine’s party for other singles) to the spectacularly creative. Activities in the latter category include taking a skydiving lesson or booking an exotic trip.The point is do, don’t stew. And listen to Elizabeth Newmark, a 45-year-old account coordinator based in Miami: "Take some time to stop and smell the roses — even if you have to send them to yourself."Do you have a tough question about dating or relationships?E-mail Sherry at and your question might be featured in an upcoming column.Email Sherry About Sherry AmatensteinSherry Amatenstein, MSW, is the author of Love Lessons from Bad Breakups and The Q&A Dating Book. She runs dating seminars around the country and does private coaching — not to help singles marry in 60 days, but to uncover their blocks. She has given relationship advice on the Early Show, Regis, Inside Edition, CBS News, VHI, BBC, and many other programs. Her philosophy is that the most important relationship you’ll ever have is with yourself.Schedule a one-on-one coaching session with Sherry Buy Love Lessons from Bad Breakups Buy The Q&A Dating Book Originally published on, February 2007.

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