How to Not F*ck Up Valentine’s Day

11 real, live, sex-having women on their best and worst V-Days

January 24, 2017 9:00 am

Dubious origins notwithstanding, Valentine’s Day matters.

You know it. She knows it. And all the friends she’s gonna talk to if you screw this up know it.

So before you go buying out-of-season flowers or heart-shaped disappointments, heed the advice of 11 real, live, sex-having women who recently regaled us with tales of their best and worst V-Day adventures.

Karen, 35, Digital Content Strategist
Married. Into it.
Best: “This guy I was dating made me a pasta dinner from scratch, got me a rose and spent two hours going down on me. Ultimate.”

Jennifer, 30, PR Executive
Single AF
Worst: “I decided to make his favorite, tiramisu, while wearing lacy lingerie. Basic, but whatever. Mid whipping the egg, his phone rang and he answered with sort of a soft voice. Clearly a girl on the other line. I was in shock that he even answered, and even more in shock that he kept talking to her, right in front of me. Turns out it was an ex-girlfriend who he was close with who was feeling sad on Valentine’s Day and called him. I crept into the bathroom with my bowl of non-fluffy eggs and cried on the floor.”
Advice: “If your person wants a special Valentine’s Day, go for it. If your person doesn’t, don’t be upset. Don’t be selfish. Don’t make it about you, make it about your person.”

Nikki, 46, Dermatologist
Divorced. Working more than dating.
Best: “Foot rub. Wine. Sex. Bed.”
Worst: “So who was that jewelry I saw for then?”
Advice: “Do something you both enjoy. If she expects to be wined and dined, you’ve got bigger problems than Valentine’s Day. And try not to fall asleep while we put on lingerie. Those contraptions can be tricky to get into, mkay?”

Andrea, 30, Producer
Got engaged. Boom!
Best: “My to-be husband and I decided to go to dinner, but there was no acknowledgement about it being V-Day. I was playing it cool like it was no big deal, but was like, ‘Um, HELLO.’ I started getting bummed because he had clearly not done a damn thing. Just as the pouting began, our server walked up to our table with a MASSIVE balloon bouquet and flowers and the entire restaurant started clapping. WELL DONE.”
Advice: “You don’t need to go over the top. just a sweet gesture or little surprise to show her you care.”

Frances, 32, Creative Consultant
Married and stoked about it
Best: “The time my boyfriend in middle school bought me the cucumber-and-melon gift basket from Bath and Body Works AND Curve perfume, because I loved them both. Combo was killer. Pure extravagance.”
Advice: “Silk pajamas. You’re welcome.”

Mona, 28, Content Strategist
Feeling out the scene
Worst: “A total cliché. I had just started dating the guy and he showed up with red roses and baby’s breath, took me to a stuffy fancy restaurant, wanted to hold my hand the whole time. No thanks.”
Advice: “Plan something fun and low key based on what I love to do and don’t take it too seriously!”

Otto, 35, Magazine Editor
He’s a keeper
Best: “Last year my fella and I went to a … hm, was it a sex party? … a fringe sex/dance party? And it was good hot fun. Easy, original and we both totally scored.”
Worst: “Whiskey dick.”
Advice: “Just ask her what she wants to do for f*ck’s sake, and save yourself the headache.”

Victoria, 26, Artiste
Single. So what?
Best: “My boyfriend at the time surprised me with a dinner reservation at this posh French restaurant that I’d been dying to try. He was an unemployed student at the time, so we didn’t go on many fancy dates, but he pulled out all of the stops on this one.”
Worst: “Said boyfriend and I had just broken up and I had hooked up with someone in my friend group the week before Valentine’s Day. I was kind of into him. Then, Valentine’s night when we were out together with a bunch of friends, he took home another girl right in front of me. That was a punch in the gut.”
Advice: “Be thoughtful.”

Lily, 27, Marketing Coordinator
My Facebook status says ‘single’
Best: “My BF turned his mom’s kitchen into a “restaurant” and made a three-course meal that I ordered off of a handwritten menu.”
Worst: “Got tequila drunk at a friend’s and passed out during my ‘real’ Valentine’s Day celebration, which consisted of a virtual movie date with my man. We broke up the next day. Oops.”
Advice: “Make a sweet, simple gesture. But make one.”

Jean, 30, Financial Services
Advice: “Valentine’s Day is the worst. I hate feeling obligated to celebrate this sh*t, or being made to feel shitty because I didn’t. Take the opportunity to do something romantic on a non-predetermined day.”

Julia, 30, RN
Hooked this guy
Worst: “Being too full from dinner and having the most raging UTI in new lingerie.”  
Advice: “Don’t sweat the holiday for what it’s been molded into. Flowers and fancy dinners are nice, but chances are someone’s done it for her before. Do something personal.”

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