Ask Anna is a sex column. Because of the nature of the topic, some columns contain language some readers may find graphic.
I’m single for the first time in four years. What should I do with myself on Valentine’s Day? — Singles Awareness Day
Whatever the hell you want! Do something, do nothing, do everything. But remember that the best part about being single on V-Day is that you don’t have to participate in all the nonsense. No partner to be butt-hurt that you didn’t get them an 8-foot teddy bear, no in-between person you’re dating left wondering if the day “means” anything, no ornery spouses to feel utterly crushed when you forget the day entirely and don’t even tell them they look cute today.
Truly, the day is yours. Enjoy your freedom. If you want to make it a self-care day, I’m all about that. If you want to hang with friends, do that. If you want to go watch an obscure Polish silent film and eat queso dip with your bare hands, oh my god, please do it! Treat yo’self in whatever way feels best to you and your body.
What gift should I get my wife for V-Day? — Anon.
I am certain you are way better qualified to answer that question than I am. But I will say this: Unless she’s specifically asked for a thing, don’t make it a gift — make it an experience. Go on a scavenger hunt at the Art Institute. Go ice skating at Millennium Park. Sip fancy cocktails at a secret bar (The Drifter, Violet Hour and Ladies Room are all fun.) Give the hard-working florists a break, and experience some living plants and flowers at the Chicago Botanic Garden or Garfield Conservatory. Soak in some hot water at AIRE. Whatever you choose, we’re much more likely to fondly remember an experience than we are to receive an object — even an object we really, really like.
How do I handle Valentine’s Day as a poly person? I have three partners at the moment and want all of them to feel special. But divvying up the day for each feels weird and exhausting. What should I do? — Many Valentines
An ex’s ex used to handle the day by ignoring all of his partners and instead doing his taxes. Which is one option, albeit a bit avoidant/heavy-handed. Of course, you should talk to your partners first and find out how they feel about the day — some people couldn’t care less; others (like me!) want some extra attention on VD. But if you’d like to make each person feel cherished, you don’t need an Official Day for it. You can do it at any time, and you absolutely should.
Choose a week, and plan a special date for each partner based on who they are and what they love. And I do mean plan it. Don’t ask a thousand questions about what they want. Ask one or two, then do the research yourself and make the decisions. These dates don’t need to be on or around Feb. 14, but they can be if that’s convenient. (It is on a Friday this year, after all.) Then, when that’s all set up, on the actual V-Day, make sure you have one small gesture for each person. It can be as basic as a card (or hell, a piece of paper folded in half, Ron Swanson-style).
Making someone or several someones feel special occurs at the level of the gesture. It’s showing up. It’s honoring and remembering their favorite things. It’s putting gas in their car when the tank is empty or putting a few bucks on their Ventra card if you notice it’s low. It’s letting them have your leftovers. It’s doing the dishes without being asked when they’re tired. It’s holding their hand even when it’s freezing outside because you know they like to feel the comfort and warmth of your palm. Holidays come and go, but the gestures we remember. Good luck, MV.