There's a dark side to Valentine's Day that many of us fear as the date draws near. You know who you are. You're the one who's juggling two boyfriends, sleeping with the boss, or cheating on your wife—with a man.
Your anxieties about finding the perfect candlelit restaurant and romantic gift are compounded by the fact that the person (people?) you're finding these for don't exactly fit the Valentine's Day mold. If you want to reduce the damage you've been courting all year, follow these steps and turn your personal entanglements and dubious choices into an asset.
1. If You're Married with a Mistress
• Video: Nora Ephron’s Top 11 Romantic Comedies Lots of men will envy Jack—at first. He has a cool job, a boyish face at fiftysomething, and no obvious financial worries. Last year, he found himself giving Valentine baubles to two women: his wife and his mistress. This year, however, as Jack tries to end his extramarital affair gracefully, he's not sure how to deal with the 14th. Will a gift of jewelry send his soon-to-be-ex mistress the wrong message? Or is it simply the right thing to do, regardless of the affair's imminent demise?
In many ways, Jack appears to be a player, shrewdly attentive to details other men might overlook. Last year, when he bought a gold bracelet for his wife and a gold heart for his mistress, from two different jewelers, he paid cash for both.
Staying away from credit cards is clever, but giving his girlfriend a sentimental gold heart was a mistake. If Jack had given her the more versatile bracelet instead, she would be able to look at it without bursting into tears when, reluctantly, she comes to terms with his departure. The gold heart will be freighted with annoying, painful memories for quite some time. She'll put it in a drawer and wear it to Jack's funeral one day.
If you want her to like you when the affair has to end, give your mistress a more practical trinket, something she can wear at all times with gleeful pride. This year, Jack needs to reverse his thinking: Give a sturdy bracelet to his mistress and a whimsical heart-shaped gift to his wife—to lighten the post-affair marital mood.
2. If You're Secretly Dating the Boss
It goes without saying that clandestine inter-office Valentine gestures should be as low-tech as possible to avoid electronic embarrassment. Happy couplings are sometimes resented by others in the same workplace who suspect you're getting special treatment. Anonymous handmade cards made from doilies and signed "Guess Who?" are impossible to FWD to your colleagues. Your Valentine greetings should also be as ethereal and poetry-scented as possible, with no concrete references to gratitude—which could imply favoritism—or lust.
3. If You're Seeing Two Men at Once (Unbeknownst to Both of Them)
Sometimes being alone on the 14th is Cupid's divine plan. In one case, a woman with two New York boyfriends worried for weeks about how to spend the holiday with one guy and not the other. The boyfriend least likely to question her alibi—"A funeral in another country"—was the guy she actually wanted to be with that night. "But I was prepared to make that sacrifice and see the nosier one just to keep the peace."
When travel and business made it suddenly impossible for both men to be in town themselves, she was rendered dateless. "I'd been seeing them both on the sly because I really feared being alone, and yet here I was, facing my worst phobia on Valentine's Day. I felt grateful, like I had just dodged a bullet." Or should that be an arrow?
4. If You're a Call Girl with a Lovesick Client
For some sex workers, February 14 is a merry, almost patriotic occasion to dress up in red undergarments and make charming sales calls to regular clients. For others, it's complicated. Many call girls can't help but be emotionally seductive at work; as a result, their clients can't quite believe the nice girl they met through that Web site is really a hooker. Some customers—if you never mention the existence of a love life—will convince themselves that seeing you once a week for a few hours is the same thing as being your boyfriend.
In these cases, you can't afford to discourage your most besotted regulars. If you have a date with your real boyfriend this Sunday and an infatuated customer asks you to be his Valentine, a clear "no" may cause your customer to suddenly lose your phone number. (It's so much easier to juggle boyfriends and customers on a weekday!) And telling a client you're sick in bed is never wise, but nor is telling your boyfriend as much, lest he rush over with soup and flowers.
If the client in question is a generous and steady customer, make plans with him anyway. Let him know you regard him as Valentine's Day material, in case you happen to be available next year, when it falls on a Monday.
Then, a few days before your date, you are unexpectedly summoned out of town by your mother. (Call girls never live in the same town as their mothers, and if they do, they certainly don't let their clients know.) Do not apologize for having to cancel. Instead, call him on the 15th to indicate you were the tiniest bit disappointed not to have received a Valentine's text on the big day. (You did, of course, give him enough time to book an appointment with someone else, whose existence you will pretend not to know about.)
5. If Your Valentine Is a Call Girl
Lingerie as a gift is often embarrassing. If that's what you have in mind, send her a gift certificate 10 days before, so she can shop for a great-looking item that fits her perfectly.
Also, don't take it personally if your favorite escort prefers brunch in bed to dinner and a show. If she suggests an early morning appointment, tell her you're deeply flattered that she wants to see you first thing. A working girl is more sensitive than you realize. Whether she's always telling the truth or not, her efforts to make things go smoothly for you are sincere. Don't question it!
6. If You're a Husband on the Down-Low
If your wife is in the dark about your erotic adventures with other men, you're not the only one. Likewise, if you think the gay men you're secretly sleeping with don't care about romance, you've never seen all those same-sex Valentine's cards in the gay gift shops. Robert Johnson, a bisexual escort, says some of the most politically correct gay men who preach about committed relationships "are secretly having sex with straight married men." Will yours be petulant or oblivious on the 14th ? To preserve your happy home, you'll need to find out.
A leisurely lunch with another guy two days before Valentine's Day is unlikely to generate gossip as long as the setting is dignified. It's an opportunity to sound him out, and to discern his attitude—and his sweater size. If he's not into sweaters, consider cufflinks, but only if you're a cufflink owner yourself. Just in case your wife finds them hidden in the dresser.
Your wife is alert to your behavior in ways that a man won't be, so don't make the mistake of doing everything perfectly on this of all days. If you're normally a bit detached (a distinct possibility, considering your little side project), being suddenly compulsive about arranging the Godiva chocolates amongst the rose petals on the linen tablecloth at the impossible-to-get-into candlelit restaurant might make you seem like a human Hallmark card. She may wonder why you're so different from other hetero dudes who tend to be more absent-minded about Valentine's Day. Ordering flowers way ahead of time while drawing attention to the chocolates you forgot to pick up strikes a good balance.
7. If Your Romance Goes Kablooey Right Before Valentine's Day
Three months ago, when Shantae Whisby told her boyfriend she had once stepped out on him, she had no idea it would lead to a breakup right before Valentine's Day. "He was checking my Facebook, and the guy I cheated with still writes me," she says. "I'm trying not to be a bitter woman. I'm so mad because when I changed my ways is when the breakup happened."
Her advice? Women in her position must simply "pull out that black book, dust it off, and go to work calling all the men in, so you won't be lonely on V-Day." She's planning dinner and a movie this Sunday with the man who is "the reason I am single now." After the 14th, they'll remain friends, she says, "because we know each other too well. We cannot be an item. I was the sideline when he had a girlfriend."
8. If You Break Up Right After Valentine's Day
Some of you gals simply refuse to end a romance before Valentine's Day because you can't say no to a present—and a few can truthfully state that their early-March breakup was purely a coincidence. But after you've just received that expensive bottle of perfume or the La Perla undergarment set (which you're now free to wear with your next romantic conquest), is it really possible to call it a day without making your Valentine feel exploited?
After a grace period of at least five days, a subtle campaign to make your lover so jealous and irrational that he manages to offend you is one time-honored method. I know of a man who was so provoked by his girlfriend's antics that he was calling her names by early March and leaving judgmental voicemails—which she saved as "evidence" of his despicable "sexism." Despite his apologies, their relationship had to end and he took the blame—but this is a dangerous game. Quit while you're ahead.
Tracy Quan's latest novel is Diary of a Jetsetting Call Girl, set in Provence and praised in The Nation as a "deft account of occupational rigors and anxieties before the crash." Tracy's debut, Diary of a Manhattan Call Girl, and the sequel, Diary of a Married Call Girl, are international bestsellers. A regular columnist for The Guardian, she has written for many publications including Cosmopolitan, The Financial Times, and The New York Times.