How to Casually Date Someone When It's Almost Valentine's Day
“Dating is confusing and weird” is a text my friend sent last night to a guy she went on a date with recently. That’s true year-round, but especially right before Valentine’s Day. Going out with someone casually in the days leading up to the big, romantic holiday can be stressful. Does the other person think you two are “valentines”? Do they want to be? Do you want to be? How can you communicate what you want and figure out what they want without making it, as my friend said, confusing and weird?
The reality is, you may not be ready for (or interested in) the mushy cards, the expensive dinners, the rose petals, the declarations of eternal love, or making the relationship Instagram official—if it’s even a relationship at all. An impending holiday dedicated to relationships can give you a sense of urgency you might not have had if you met this person in, say, June. While there is no reason to speed anything up or add stress to something new, if you want to make plans on Valentine's Day with the person you’ve been sorta-kinda-maybe dating, more power to you. But first, you need to figure out how you feel and what your approach is.
Assess your feelings on Valentine’s Day first
Before you even think about what the looming holiday means for the person (or people) you’re seeing right now, take some time to think about what it means to you. In the past, have you cared about the day when you were in a relationship? Will this be your first single Valentine’s Day or are you a little more used to it? If being without a significant other on February 14 is relatively new for you, that could be causing some of your stress, but you don’t want to mess up what could be a nice thing with someone else by projecting your own internal battles onto a new fling.
Ari, a 28-year-old single woman in Philadelphia, tells me she has a first date tonight, but isn’t worried: “Valentine’s Day is a made-up concept for capitalism. Fuck that noise. There are no implications [to going out with someone before the holiday]. Who cares?”
Whether you’re a romantic who yearns for a day during which someone has to express mushy sentiments toward you with gifts and cards, or you're more of the cynical type, spend time figuring out how you feel about the day, then a little more time assessing the relationship you have with your are-they-aren’t-they valentine. Do you really like this person, or is your stress stemming from the prospect of being alone on the big day? Do you think they might like you more than you like them and, thus, want to do this holiday with you in a sincere way?
Be a clear communicator
If you’re feeling a certain type of way about Valentine's Day coming up, it’s best to be honest with the other person. Bring it up and set realistic expectations. If you want to celebrate with a casual or new partner, you don’t want to be disappointed if it doesn’t materialize. On the flip side, you don't want to have them be disappointed if you're not into the holiday.
Regardless of where you fall, make sure you’re on the same page. You could say, “Hey, I know we just started seeing each other but I love Valentine’s Day and it could be fun to do something for it.” Or, “I’m not really into Valentine's Day myself, but let me know if that's something that's important to you.” While this could feel a bit awkward at first, it’s still better than planning a big surprise and it falling flat.
Rose, a 30-something in NYC, has been talking to a woman from another part of the country for a few weeks and really likes her. The woman has been planning a trip to New York to meet Rose and when they were discussing dates, she suggested February. Rose asked, “So do you wanna be my valentine, eh?” The woman said she did, in fact, want to be Rose’s valentine, and the conversation was easy and quickly over, all via text. Even something as simple as a gentle cutesy text can help you both get on the same page.
“I was in the early stages of dating someone last year during Valentine’s Day, and because he didn’t want to have a conversation about where the dating or the relationship was heading, he ultimately ignored Valentine’s Day until I brought it up because he didn’t want to put pressure on things,” Rose recalls. “So I think the holiday weirdness is a symptom of a larger communication issue.”
If someone is avoiding talking to you about this altogether, it might be time to accept that person is not your valentine, nor a good potential partner for the other 364 days of the year.
Make other plans for Valentine’s Day
All that said, if you’re only two or three dates in with someone, it might be a good idea to skip the holiday altogether. If things work out between you, there’s always next year, and all the holidays and birthdays between now and then. Applying pressure to something so new could freak the other person out or drag you both into more serious territory before you’re ready or even know if the relationship is going to go that way.
If you’re feeling weird about it, make other plans, preferably something fun with friends. This gives you something concrete you can point to if the other person asks what you’re up to that night and, if they seem really disappointed, you can get a better sense of what their intentions with you are (and bail on your friends, if it’s that serious, but only if you think this person is the love of your life). Steph, another New York singleton, says a few of her friends have a standing dinner reservation together every February 14 to ensure they all have something to do, regardless of each of their relationship statuses in a given year.
Go for it
If you want to do something, go for it! But when in doubt, perhaps forgo the fancy dinner and expensive gifts. A grand gesture is probably not the best move here but something small, thoughtful—or even humorous—could be sweet. You could offer to see a movie together, get drinks, or even stay in and order take-out. If you want to make things cuter, feel free to get them something small like the classic flower bouquet or a box of candy. It’s simple and sweet and communicates that you’re happy to be dating them. If heart-shaped candy is a little much, try these easy workarounds from Target:
A cute red mug ($5) to make…
…hot chocolate with these cocoa drink bombs ($4)
“Don’t let Big Romance get in the way of your good time,” says Ben, a 32-year-old dater from California who loves Valentine’s Day and has even used it as a first date opportunity in the past. (“We had a great time!”) If you love love or just love holidays, don’t let the stress or awkwardness get to you. Embrace it and show the other person what matters to you. That’s what the early stages of dating are all about. The pressure, Ben says, “is all self-imposed.”