6 Struggles of Dealing With Valentine's Day in NYC

Everyone knows it's way too typical of millennials in the millennial dating scene to avoid labeling a hookup for as long as possible.

Are we afraid of vulnerability? Probably. Do we enjoy reaping the benefits of a relationship without the pressures of commitment? Definitely.

No matter what factors pushed millennials into this situation, the reality is that we're here. Plenty of us have someone on our speed dial for when we want to cuddle or hook up, or when we're drunk and it's Saturday night.

The problem? Valentine's Day is a day that's designed for couples. Everyone does romantic stuff like buy each other flowers and eat out at restaurants. 

So, if you're in a hookup in which you haven't yet had the "what are we?" conversation, handling Valentine's Day might be difficult. Read on to learn about the struggles you probably know all too well.

1. Making plans

kawaii_____potato I want this card for valentines so I can contemplate how lonely and depressed I am ๐Ÿ˜ƒ #loner4life #valentinesdaysucks

Texting someone saying, "Hey, want to hang out on Saturday?" becomes a much more turbulent situation when that Saturday is the Saturday of Valentine's weekend.

This is where the struggle lives. Do you just pretend it isn't Valentine's Day and ask your hookup to hang out as though it's any other weekend?


Or do you completely avoid texting your hookup all weekend, possibly sending the message that you aren't interested in anything romantic at all?

Most of all, you definitely get irritated with yourself for stressing so much about this particular struggle.

2. Buying presents

mark_brucewayne_brown Yeah its going to suck this year. Nothing new to me. Lol!!! Not going to be single forever. #teamsingle #temporarilysingle #valentinesdaysucks

If you do wind up hanging out with your hookup during Valentine's weekend, the question of what to buy them will hang ominously above both your heads all weekend.

We're generally against clichรฉd ideas like red roses and candy if you're in an undefined situation. Unoriginality is not your friend here.

The best move is to do something funny, like buying the other their favorite type of chips or alcohol. That'll prove that you know the person well and care, but that you're not necessarily putting any romantic pressure on what's happening.

3. Telling your parents

andramalama Super super EXCITED to announce my zine is printed and ready. There's a link to my etsy shop in my profile or you can DM me for a copy. I am charging 2 bucks to cover shipping and supplies ๐Ÿ˜‹ (if you really can't pay it no worries or let's trade!!) #arewedating #zine

Your parents want to know what you Valentine's day plans are. Let's just assume you're entrenched in your hook up enough that you're hanging out on Valentine's Day, but not deep enough that you're ready to tell your family you're in a relationship.

Still, your parents will call and say, "What are you doing for Valentine's day?"


Of course, you can't answer honestly. You can't stay, "Just hooking up with someone, but there aren't strings attached!" 

The question is, should you lie and say you're hanging out with your friends? Or instead exaggerate the extent of your hook up's potential? 

Either way, the struggle is vexing.


4. Telling your friends you can't hang out

thereal_high_fi N u.o.e.n.o it... ๐Ÿ˜‚๐Ÿ’ฏ....#ValentinesDayStruggles

It's definitely a time honored tradition for single friends to get together on Valentine's day and drink hard.

However, if you're involved in your hookup enough that you're hanging out on Valentine's day, you're going to have to tell your friends why you're not coming to dirty bingo with them.


When you say you're going to be hanging out with that person you sometimes hookup with, they're going to put a lot of pressure on you to say whether you're in a relationship or not.

Don't give into the pressure to define your romantic situation. You're not in a committed relationship yet, and that's okay. Valentine's day does not need to rush it.

5. Deciding where to go

staceycakes510 Ummm, yeah. Pretty sure this will be me. Except it will be tequila instead of coke. #valentinesdaysucks #SingleLife #Solo #NotTrippinTho #SingleAF

This is another issue, because the more upscale of a restaurant you go to, the more romantic it seems.

This is especially true because since Valentine's day is the second most popular day in the restaurant industry, restaurants have taken great care to make the atmosphere romantic. They've likely got a whole flower and candle situation set up.

If you and your hookup are hanging out the night of Valentine's day, you do have to eat. Ordering takeout is too casual, and eating at a fast food place is too depressing.

A really great happy medium to strike is if you cook together. Also, ordering a pizza together might be nice.

6. Figuring out who pays

tee_coe Current Mood ๐Ÿ‘Œ๐Ÿ™…โค๏ธ #valentinesdaystruggles #meh

If you do go out to eat, and you find a pretty moderately priced restaurant that won't put too much pressure on your hangout, you'll still have even more trouble by the time the check comes.

If one person pays for the entire meal, it's definitely a date. If you split the bill, it could either be a date or a casual go-out-to-eat situation. Splitting the bill leaves things much more ambiguous.


Picking up the check can be a pretty stressful Valentine's day situation, but at least there are more stressful situations out there. Like, taxes and the day your monthly MetroCard runs out. 

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