An entire day dedicated to declaring your love for someone? If you’re casually hooking up or in a new relationship, Valentine’s Day can be awkward.
The reality is you may not be ready to write each other mushy cards, spend money on an expensive dinner, or say “I love you,” if you’re not at a full blown BF/GF status. Don’t allow an artificial date on the calendar make you feel pressure to speed things along or force a ‘define the relationship’ (DTR) talk if you’re not ready.
If you just started dating, it may be best to hold off on celebrating all together. When you’re not in an exclusive relationship, singles tend to date multiple people at the same time, so the person you’re seeing may already have plans, or even be further along in a relationship with someone else—I know that’s a buzz kill. Send out some feelers to figure out whether his intentions are to celebrate with you,
If in general it just feels like too much pressure, do something else that’s a guaranteed good time, such as throwing a Pinterest-worthy wine and chocolate party with your friends, or cozying up with some cocoa and a romcom. Do what makes you feel good, and remember that there’s no right or wrong way to celebrate V-Day.
On the flip side, if you’ve been dying to make it official and ready for a committed relationship, Valentine’s Day may be the perfect occasion to ask your potential significant other to “Be mine?” My husband asked me to be his girlfriend at the end of a poem he wrote for me in my Valentine’s Day card a few months after we began casually dating!
If you’re thinking of making it official, just be sure signs are pointing in the direction that these feelings will be reciprocated. For instance, has he been putting in effort to court you, make you a priority, and lock down future plans with you, or is he a Netflix and chill kind of last minute guy?
Regardless of where you fall from casual to committed, the recipe for a successful Valentine’s Day is making sure you’re on the same page.
It’s important to set realistic expectations to avoid a potential misalignment of effort put into celebrating. Unless you have magical powers, no one is a mind reader. This means you actually have to talk about Valentine’s Day in advance.
If you’re unsure about whether you’re even hanging out for the holiday, ask, “What are your V-Day plans?” or boldly say, “I’d love to spend Valentine’s Day with you, are you available?” Otherwise, you’ll be disappointed if the day goes by and you don’t even get a call, let alone a card.
The truth is a guy who sees you as girlfriend material will likely already be planning something sweet. If it’s confirmed you’re going on a date, but you’re unsure if you need to do anything above and beyond spending time together, it’s best to keep things simple. Homemade baked goods are always a slam-dunk.
If your new partner doesn’t want to do something special for Valentine’s Day and you do, this suggests he’s just not that into you, or may signal important information about clashing values.
Valentine’s Day, like many holidays, often tap into traditions and messages you’ve internalized since early childhood. Did your parents make V-Day a big deal at home, giving cards, gifts, or even leaving the kids at home for a romantic date night or getaway? This may influence both of your outlooks on the holiday, and can represent someone’s core values about things such as money management, materialism, or provide insight into your love languages.
Discussing how you feel about the holiday and why gives you a lot of insight into the person you’re newly dating. Learning about your differences may be enough to make you realize this relationship isn’t going anywhere, or that you’re incompatible as a long-term match. 
