How to Casually Date Someone When Valentine’s Day Is Coming

“Dating is confusing and weird” was a message my friend sent last night to a guy she recently went on a date with. This is true all year round, but especially around Valentine’s Day. A casual date with someone in the days leading up to a big romantic holiday can be stressful. Does the other person think you two are “Valentines”? Do they want to be? 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 that you may not be ready (or interested) for soft cards, expensive dinners, rose petals, declarations of undying love, or making the relationship official on Instagram—if it is even a relationship. An upcoming relationship vacation can give you a sense of urgency that you might not have had if you had met this person in, say, June. While there’s no reason to rush anything or add stress to something new, if you want to make Valentine’s Day plans with someone you’ve been kind of dating, more power to you. But first you need to figure out how you feel and what your approach is.

First, evaluate your feelings on Valentine’s Day.

Before you even think about what the upcoming holiday means to the person (or people) you’re currently dating, take some time to think about what it means to you . In the past, have you cared about the day you were in a relationship? Will this be your first single “Valentine’s Day” or are you already used to it? If not having your significant other on February 14th is relatively new to you, it may cause you some stress, but you don’t want to ruin what could be good for someone else by projecting your internal battles onto another person. new intrigue.

Ari, a 28-year-old single woman from Philadelphia, tells me she has her first date tonight , but she doesn’t care: “Valentine’s Day is a made-up concept of capitalism. Fuck this noise. There are no consequences [to meeting someone before the holiday]. Who cares?”

Whether you’re a romantic longing for a day where someone has to express soft feelings to you through gifts and cards, or you’re a more cynical type, take the time to figure out how you feel about the day and then take a little more time to evaluate your relationship with your lover. Do you really like this person, or is your stress caused by the prospect of being alone on your big day? Do you think that they like you more than you like them and therefore will want to sincerely spend this holiday with you?

Be a clear communicator

If you’re feeling a certain way about Valentine’s Day approaching, it’s best to be honest with the other person. Raise the issue and set realistic expectations. If you want to celebrate with a casual or new partner, don’t be disappointed if it doesn’t come to fruition. On the other hand, you don’t want them to be disappointed if you don’t enjoy your vacation.

No matter where you end up, make sure you’re on the same page. You could say, “Hey, I know we just started dating, but I love Valentine’s Day and it would be fun to do something for it.” Or, “I’m not a big fan of Valentine’s Day myself, but let me know if it’s important to you.” While this may feel a little awkward at first, it’s better than planning a big surprise that doesn’t go well.

Rose, a 30-year-old New Yorker, has been dating a woman from another part of the country for several weeks and really likes her. The woman was planning a trip to New York to meet Rose, and when they discussed dates, she suggested February. Rose asked, “So you want to be my lover, huh?” The woman said she really wanted to be Rose’s lover and the conversation ended easily and quickly, all via text message. Even something as simple as a sweet, sweet message can help you both find common ground.

“I was in the early stages of dating someone last year around Valentine’s Day, and since he didn’t want to talk about where dating or the relationship was going, he ended up ignoring Valentine’s Day until I brought it up question because he didn’t “I don’t want to put pressure on the situation,” Rose recalled. “So I think the weirdness of the holiday is symptomatic of a larger communication problem.”

If someone is avoiding talking to you about it altogether, perhaps it’s time to admit that this person is neither your crush nor a good potential partner for the other 364 days of the year.

Make other plans for Valentine’s Day.

However, if you only have two or three dates with someone, it might be a good idea to skip the vacation altogether. If everything works out between you, there is always next year ahead, and between now and then all the holidays and birthdays. Putting pressure on something so new can scare the other person or drag you both into more serious territory before you’re ready or even know if the relationship is going that way.

If you feel weird about this, make other plans, preferably something fun with friends. This gives you something concrete to point to if the other person asks what you’re doing that night, and if they seem really frustrated, you’ll be able to better understand what their intentions are towards you (and save your friends , if it’s that serious, but only if you think that this person is the love of your life). Steph, another New York City single, says several of her friends make regular dinner reservations every February 14th to ensure everyone has something to do, regardless of their relationship status in a given year.

Take action

If you want to do something, do it! But if in doubt, maybe skip the fancy dinner and expensive gifts. A big gesture is probably not the best move in this case, but something small, thoughtful, or even humorous can be nice. You could suggest watching a movie together, having a drink, or even staying home and ordering takeout. If you want to make things sweeter, give them something small like a classic bouquet of flowers or a box of chocolates. It’s simple and sweet and shows that you’re happy to be dating them. If heart-shaped candy is too much, try these easy workarounds from Target:

• Cute red mug ($5) to make…

• …hot chocolate with cocoa bombs ($4)

• And a strawberry dipping kit ($9).

“Don’t let big romance stop you from having a good time,” says Ben, a 32-year-old from California who loves Valentine’s Day and has even used it as an opportunity for a first date in the past. (“We had a great time!”) Whether you’re a lover of love or just love the holidays, don’t let stress or awkwardness get the better of you. Accept it and show the other person what is important to you. This is what the early stages of dating are all about. The pressure, Ben says, is “completely self-imposed.”

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