What you might be tempted to do: Reference the “awkwardness” of the situation. Texting a girl “Happy Singles’ Awareness Day!” or making some snarky comment about how your date falls on V-Day has been done before, probably by every other man she’s talking to on apps and deciding which one of you guys she’ll actually go on a date with. Showing any dissatisfaction towards being single makes it seem like you’re bitter or sad or desperate (or all of the above) and no one wants to date someone like that. Don’t make it weird, bro.
What you should actually do: Plan a casual date—coffee, drinks, etc.—just like it’s any other Tuesday. If she brings it up that it’s Valentine’s Day, fake some ignorance and say, “Oh! I didn’t even realize that! Do you still want to meet up?” Playing it cool is the best way to go and more than likely she’ll say yes (after all, it’s fun to have a first date on Valentine’s Day). If you want to bring her a single flower on the day of—not a bouquet of red roses, unless you want to look like Norman Bates—to give a nod to the holiday without going all out, it’s a sweet touch. Hot tip: White flowers are classy AF, and lilies are daisies always do the job.
ZERO TO THREE MONTHS:
What you might be tempted to do: Do a simple date like go to the movies. And I get it—your relationship isn’t really set in stone yet. You might still be feeling each other out. You might not have even had the “what are we” talk, and that’s fine. But there’s a gray area—it’s too early on to do something extravagant. If you’re not super into her, she’ll read into the situation. If you are super into her and come on too strong before she’s figured out her feelings for you, don’t be surprised if you catch her texting during the date—it’s her best friend and she’s telling her EVERYTHING.
What you should actually do: At the end of the day, it’s so early on in the relationship and you’re still getting to know one another. A simple date at a casual restaurant—none of that price fixe stuff, nothing that requires a reservation weeks in advance—is sufficient. Whatever you do, don’t go to the movies: it will be filled with teenagers whose mom drove them to the theater and you’ll be surrounded by raging hormones and greasy faces swapping saliva for two to three hours. You also can’t even actually talk to each other, which is a lady boner killer.
THREE TO SIX MONTHS:
What you might be tempted to do: Go all out. You’ve had “the talk,” you’re a real, bonafide couple, and experiencing the fun early-on-in-the-relationship period where you’re obsessed with each other. You want to impress her and show her that you care! You want to buy her ALL THE THINGS and take her to ALL THE PLACES. But slow your roll, dude. Because the moment you go out to the fancy restaurant, you’ll be spending a ton of money (restaurants jack up the prices for a typically smaller menu) on the novelty of going out on Valentine’s Day and not necessarily on good food. Remember, spending a ton of money isn’t going to impress her the way you think it will (and if it does, you’re dating the wrong girl).
What you should actually do: Cook dinner—together. Any dude with opposable thumbs can dial a phone to make a reservation. It takes two seconds and requires very little effort. Make it a collaborative effort: decide on a recipe you two want to try ahead of time, go out and pick up the groceries for her and then get down to business. Working on something together—especially a meal you can enjoy together—will prove how you two work as a team. Can’t cook? Even if you burn the garlic bread or overcook the pasta, it’ll be a funny memory the two of you can share.
SIX MONTHS TO ONE YEAR:
What you’re tempted to do: Buy her a lavish gift. Don’t get me wrong—candy and jewelry are nice (and us women love to Instagram that shit). But it’s still too early on to get your partner that something that will put a serious dent in your paycheck, we promise. Spoiling your partner when it hasn’t been a year yet is just getting ahead of yourself, and might even freak her out a little if you gift her something so intense she thinks you guys are on separate pages of where your relationship is at After all, your relationship isn’t going to last if you have to impress each other with money and material things all the time.
What you should actually do: One of the best ideas I had with my partner (who I will be with 8 months this Valentine’s Day) was do something a little out of the ordinary. We gave each other a five-dollar limit and decided to buy gifts for each other at the Dollar Store with the goal of buying things that reminded us of each other. I’m betting now that one of my five gifts is a whoopee cushion. We also decided to make each other homemade cards… in MS Paint. I’d suggest this activity to any couple because if you can’t laugh together, what’s the point?
ONE YEAR TO TWO YEARS:
What you might be tempted to do: Plan a crazy date doing something adventurous! You’ve been together for over a year, so yeah, this isn’t your first rodeo. But while that Groupon for ziplining or laser tag or boozy watercolor class looks fun and is a good deal, the last thing you want to do is surprise her with an activity she might not be 100 percent on board with. And then all you’re stuck with are some weird painting of an apple as a Valentine’s Day memory.
What you should actually do: Plan a date specifically catered to her, not the two of you. At this point in the relationship, dates are less about what you do and more about a reflection of who you are. You’ve been on a ton of dates and know what your partner likes and what she’d really want to do. Plan a date that proves that you know her well—go for a hike, get tickets to a band she loves, go bowling. Whatever experience she would most appreciate from you is the one you should try to do. You’ve been together for over a year, and you know what she likes by now. You got this.
TWO PLUS YEARS:
You might be tempted to do: Buy her lingerie. You’ve spent a few Valentine’s Days together at this point and have done it all. You’ve done the chill dates and the sweep-her-off-her-feet dates. For the love of God, take it from a woman—please don’t buy your partner clothing of any kind (undergarments included) unless she’s explicitly stated what she wants and what size she is. Buying lingerie for a woman is like buying cologne for a man: don’t do it. Y’all are picky as hell and 99 percent of the time you end up putting the bottle in a drawer and never touching it again. The same thing’s true for chicks and bad lingerie with weird straps and lacy hearts all over it. Also, she doesn’t get anything out of it if she refuses to wear it, which means you aren’t either.
What you should actually do: If you still want to buy her a sexy gift that will be fun for the two of you, lingerie or sex toy shopping together is a fun way to spend a Valentine’s Day afternoon. Great sex is based on communication, collaboration and enthusiasm, and the same should be true for buying anything that will be coming into the bedroom with you. Stop by a few shops in the afternoon and take home some “gifts”—for the both of you—to use that night. Believe me, nothing is more awkward than gifting too-small, too frilly lingerie, or a bejeweled plug, that she definitely did not want or ask for.