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The Valentine's Day Conundrum -- What to Give or Not Give, When You're Only Dating

02/13/2015 02:53 pm ET | Updated Apr 15, 2015
Betsie Van der Meer via Getty Images

Valentine's Day can be filled with anxiety when you have a new relationship in your life. Should you acknowledge the holiday, or is the relationship too young and fresh? Should you buy a small gift? Or, maybe just send a card, in which case, what is the right tone? Should it be low-key, perhaps funny or ironic? Or, maybe, should you do nothing at all? It's a nerve-racking dilemma. The wrong move could send the wrong message. It could even sink a new relationship!

My divorced pal, Jenna, told me a hilarious story about how she handled Valentine's Day last year. She had been dating a man named Joe for six weeks. They'd met on New Year's Eve, and the relationship was in that tentative stage where the relationship looked promising, but they weren't really a couple yet. Jenna agonized over what to do about Valentine's Day. Was Joe going to give her something? Should she reciprocate, and if so, what should she give? Something too lavish might be misinterpreted, and could even scare him off if he thought she was making the relationship too serious. Giving nothing might also give him a false idea that she didn't see him as a romantic partner at all -- which could also put him off. Poor Jenna knotted herself into a ball of anxiety. She decided to wait and see if Joe sent anything to her workplace, perhaps flowers or even an e-card.

Valentine's Day came around and nothing showed up from Joe. Jenna was supposed to meet him that night for dinner, which was confusing in itself because it hadn't been presented as a Valentine's Day dinner, just dinner. She anguished all over again about how to handle the situation now.

There was no indication one way or another if Valentines Day would be acknowledged. She decided to play it safe and quickly ran out to Macy's and bought him a small, but personal gift -- a nice bottle of cologne. The store even gift-wrapped it in bright pink tissue paper and a silver bow. But wait! What if she walked into the restaurant where they'd planned to meet and he didn't have a gift for her? Jenna started sweating all over again, pondering how to handle it.

How could she conceal the gift? Could she hide it in her purse? No, it was too big now with all that fancy wrapping! Finally, she came up with the perfect solution. She would call Joe up and offer to pick him up. That way she could hide the gift in the trunk of her car. If he came out with something for her, she could quickly flip the trunk open and present the cologne.

That night Jenna pulled up outside Joe's building at the appointed time. She watched him walk out, empty handed. She quietly congratulated herself on having avoided an embarrassing situation. But then, before she could stop him, he reached into the car and flipped the trunk open -- he'd left his tennis racquet there, and he wanted to be sure he had it for a game the following day.

Jenna quickly scrambled out of the car to intervene, but it was too late. There, glowing in the wide open trunk, was the bright pink gift. Jenna's mind raced. Should she pretend it was a gift she received from someone else? No, no, very bad idea! She realized she had no choice. She bit the bullet, grabbed the gift and pushed it into Joe's startled hands. "Happy Valentine's Day," she said, her heart racing, feeling like a complete idiot. Joe's face flushed. It was, as she put it, as bright pink as the wrapping paper. Backing up, he stammered something about having left her gift inside his apartment. He hurried inside. A few minutes later, he came out with a generic-looking gift bag, which he thrust into Jenna's hands. She pretended to coo over it as she lifted out two gaudy looking painted martini glasses, the kind, she said, that you might buy at an amateur art fair or even a garage sale.

"They're lovely," she said, trying hard to smile. She then noticed a card at the bottom of the bag. She lifted it out. At this point Joe looked sick. "I didn't know that was there," he said. As she opened the card and read the words "Happy Birthday, Joe," she realized that this was a blatant case of re-gifting. He had raced inside to find something, anything, to reciprocate her gift.

Was this the end of their relationship? Was it all too awkward now? Not at all! As Jenna put it, it was a real ice-breaker for them They went to dinner and after drinking two glasses of wine, Jenna 'fessed up about contorting herself into an anxious pretzel about the gift dilemma. Joe confessed he'd had the same conversation with himself. They ended up laughing it all off. And that night, she said, was the night they consummated their relationship. It was the best gift of all, she said, and a wonderful end to a memorable Valentine's Day.

This blogger has a psychotherapy practice in Los Angeles.