As a single person, I have to tell you, mid-February is not my favorite time of year. Pink hearts abounding with no one for me to give one to, merry couples flaunting their mutual bliss in dimly lit restaurants, and, of course, the secret shame of every single girl — the flower delivery from my mom. It’s easy to understand the real reason that being single on Valentine’s Day truly sucks: you’re just plain left out.

But there are more subtle, sneaky ways that the holiday makes people miserable. Even if you’ve just started seeing someone or are officially dating someone, February 14th is a tricky date to navigate. Let me explain:

Valentine’s Day makes people afraid to start dating someone
Dating gets put on hold for the few weeks before the 14th, because who wants to go on one date with someone only to have to decide right away whether to commit to a couples’ holiday together? Say “yes” to a Valentine’s Day date, and you seem too eager. But if you don’t mention the holiday at all, you look just plain out-of-touch and may find yourself wondering why your date is so standoffish. So, many single people do what I do: put dating on a hiatus from about mid-January onward, just to avoid any awkward situations.
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Valentine’s Day can wreak havoc for those who date around
Many single people out there believe it’s wise to hedge their bets by seeing more than one person at once. That’s all well and good — until red-letter days like Valentine’s come along, where there’s only room for one name on your high-stakes dance card. You may find yourself in a position like one friend (who won’t let me use her name) who woke up one Valentine’s morning with someone she’d been dating, graciously accepted the flowers he gave her, then waved goodbye and threw them away so her evening visitor wouldn’t see the evidence of his competition. Having multiple suitors is good for the ego and if, say, you’re trying to collect all the Kung Fu Panda toys from a fast food promotional tie-in for your nephew, but it certainly makes for a lot of sticky scheduling. Not to mention the countless opportunities for direct questions like, “Well, what are you doing that night?” or worse, about the relationship’s status... how, er, completely not romantic!

Valentine’s Day forces people to be super-sentimental
February 14th also puts external pressure on singles to not only be in a relationship, but to be in a relationship that communicates through pink-and-white card stock. “I hate seeing girls carrying home flowers that their boyfriends sent them, because I know that’s never me, even when I have a boyfriend — that’s just not how I am in a relationship,” says Heather McCabe from Newark, DE. “All of the expressions have just become formulaic — why bother if you know what’s coming?” She says she’d rather her boyfriend did something nice for her unprompted than something “romantic,” just because it’s a day when he’s “supposed” to. So much focus on one little day can actually make people start to second-guess the hearts and candy they do get — is he really that into you, or did he just pick up the generic be-a-good-boyfriend afterthought gesture because it was on sale while he was on his way home?

Valentine’s Day can bring a couple to make-or-break status
If you and your date are trying to figure out “where this relationship’s going,” be warned: Have any discussions around V-Day, and you just multiplied the meaningfulness factor by 100. “Valentine’s is like a microscope,” says John Devore, a playwright from Beaumont, TX, who’s got a special perspective, since he’s been on-again, off-again with his current girlfriend for a few years. “Every move, word, sentiment or flaw is examined in detail for deeper meaning.” Try to be civil and it’s read as commitment; act wishy-washy, though, and you’re all but asking for your date to explode. Devore has an elegant description for what happens when a mundane fight takes place on February 14: “When the relationship is stumbling, Valentine’s Day is a magnifying glass that finds a sunbeam and burns your life to the ground.”

Need further proof? Consider this case of how a sweet gesture can become a neon sign blaring “get out!” to the less-into-it half of the couple. Sophie Phillips, a lawyer in Putnam County, NY, learned that the painful way when she planned a romantic weekend away. “I did the whole bed and breakfast suite in the country thing — very storybook,” she says. When her honey got there, he took one look at the overwhelmingly romantic (some might say stifling) set-up and decided that he really wasn’t ready to move in with her, as they had been discussing. Everything was seeming too couple-y, too fast for him. “Lovely timing, right by the fireplace,” she recalls.

Valentine’s Day can cause a relationship to linger... too long
When you’re in a relationship that’s on its way out, Valentine’s Day exerts a weird magnetic pull that makes you think it’s worth sticking around for a few extra boxes of chocolate hearts. Take, for example, someone we’ll call Laura, who started seeing a not-so-perfect guy early last winter. We weren’t soul mates by a long shot — he didn’t even have a TV, for starters — but he was nice enough, the cuddling helped save on heating costs, and the fact that all my friends thought he was way hot helped, too. Now, obviously I wasn’t going to break things off during the holidays... Then, post-New Year’s, when I knew we really weren’t clicking, I couldn’t help but think, “Well, I don’t want to be single on Valentine’s Day.” I worked on keeping things pleasant for at least six weeks to make it through the holiday together... but when things did unravel, let’s just say I regretted not breaking things off sooner. It would have been easier to call the relationship as being DOA earlier rather than stretching it out unhappily in the hopes of being coupled-up on Cupid’s special day. In my case, it seems, St. Valentine was the patron saint of emotional inertia.

Valentine’s Day ratchets up the pressure to have a perfect night of romance planned out
Happy, loving couples are the people who can make us single people (or unhappy couples) quite jealous. They really just get joy out of being together, so you can imagine the epiphany I had when I discovered that Valentine’s Day causes even these people angst. It happened when I was talking to my friend Jon Wilde from Durham, CT. He’s been crazy about his girlfriend since the day they met, but Valentine’s Day really freaks him out. “The first time we celebrated it together, it was a bit stressful, but I liked working to show my girlfriend how much I appreciate her — reservations at a nice place, a pretty gift, getting dressed up, that’s all fine,” he muses. “But by the next year, I felt panicked. How could I outdo last year’s plans? More time together requires an even bigger show, right? I know in my head that my girlfriend would probably be happy to just have a nice night out where she could dress up, but I’m here beating myself up trying to one-up myself. There’s no satiating my inner Valentine’s beast!”

Valentine’s Day forces you to be a mind-reader on the gift-giving front
OK, so let’s say you’re dating someone and the big, heart-shaped day is fast approaching. Do you just get a card? Some candy? Something cashmere, or 14-karat gold? It all takes on these big, strategic implications. Suzanne Tripp, a copy editor from Boston, MA, knows this scenario first-hand. “One year, I decided to treat my guy, and I made a really fancy dinner — red, heart-shaped lobster ravioli, champagne, chocolate soufflé,” she says. For all her hard work, the one thing she skipped buying was flowers, assuming that her guy would at least pick those up out of instinct. “Nothing, nada,” she says. “Here I thought I really didn’t expect anything, because I’m not into that as a holiday, but I was still wondering if this guy even knew me or cared about me at all.”

Another friend of mine had a boyfriend who had a knack for giving her exactly what she needed — a toaster, a rolling pin, a hot-glue gun — on the holiday, but the gifts had so little romantic quotient that she usually spent the evening locked in the bathroom sobbing. “I mean really, how could I not take those gifts as a sure sign that he thought of me as a pal he happens to sleep with rather than the sexy woman who rocks his world?” (By the way, this relationship survived and thrived... but the V-Day gifts were the subject of more than one relationship counseling session afterward.)

OK, I have made my case. And as you may have gathered, I’m not a big fan of February 14th and believe plenty of other people would agree. Look, I’m not saying being single is super-fantastic. Of course I’m still jealous of people who get to go home to someone who loves them and who never have to experience sitting between two strangers on an airplane. But this year on Valentine’s Day, instead of feeling extra-jealous of my hooked-up friends, I’m going to relish my lack of awkward couple dynamics and make-the-day-perfect pressure and kick back a bit.

Freelance writer Laura Gilbert contributes to The Knot, Health, Maxim, and Stuff.

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