11 Struggles Of Not Knowing If You're Going To Spend The Night

When you're just getting to know someone, there are all sorts of awkward "getting to know you" bumps you have to endure. And if you've been in a relationship for a long time and are newly single, you probably don't remember how long it takes to get to that comfortable place where you know what to expect.

In the meantime, you end up having to answer a lot of questions for yourself. It's not the most socially acceptable thing to ask your date if you should bring a toothbrush — it could come off as presumptuous. That said, we're meant to have a casual air about us, like we can easily fly by the seat of our pants and adapt to any situation we're thrown into. But at the same time, we're meant to appear adaptable and put together and comfortable. These two concepts do not go support each other. So do you risk your comforts by attending a date with nothing but your phone and wallet, or do you risk your cool-factor by coming prepared for wherever that date might take you?

I've struggled with both the discomfort of not being prepared for the next day, and the awkwardness of whipping out a toothbrush and a guilty "I knew you were going to ask me to sleep over" smirk. What I've learned is that there's no right answer. Until you get to know your partner, these "are we or aren't we?" situations will be plenty and plentifully awkward. You just have to power through and do what you're comfortable with. If you too struggle with not knowing if your date is going to lead to an overnight, these are some of the things you probably stress over before leaving the house:

Undies: To Match, Or Not To Match?


The underwear that are most comfortable tend to be a different pair than the ones you feel sexiest in. Do you go for comfort and assume it's just dinner, or do you wear the sexy pair that will pay off if you go home with your date after dinner?

Deciding Whether Or Not To Live That Shaved Life


If you prefer the shaved look, you know how miserable it is. You know how devastated you are if you shave everything only to find out dinner is the grand finale. What a waste of razor burn! That said, do you take the risk and shave it off, or play it safe and skip the razor for a surer deal?


There are some things that we wear that we don't want people to know about. Such as control tights, pasties, pantyhose up to our necks, and that pair of jeans you have to wiggle around on the floor for an hour to squeeze into. If there's a chance you're going to be getting out of your clothes in front of another human, you want to wear something that comes off easy. There's no way of knowing if the risk is worth it.

How To Mascara?


If you're the type who doesn't like to wash your face when you're at someone else's house, waterproof mascara is a must — that is, if you don't want to wake up looking like you have two black eyes. But if you are comfortable with your date, and you do plan on washing your face if you sleep over, you'll need to skip the waterproof mascara — unless you think your date has eye make up remover wipes. It's a total gamble.

How To Lipstick??

Lipstick looks great and can make you feel really powerful and sexy. However, if you plan on making out with someone, lipstick is never a good idea. After a few hours of fooling around, you end up looking like a clown who's gone through the carwash.


Bronzer always seems like a good idea ... that is, until you're faced with putting your face on someone's crisp white sheets. Avoid bronzer if there's a chance you're sleeping over. It's not the kind of mark you want to leave on a prospective lover.

Pre-Bedhead Strategizing


Sometimes it's fun to do an involved hair-do for a date. You know, the kind that requires a dozen bobby pins and a ton of hairspray and braiding? If you don't bring back-up products, these hairstyles end up looking majorly crazy in the morning. If you think you might sleep over, avoid the kinds of styles that require a lot of maintenance.

The Infamous Toothbrush Debate

Nothing makes you feel clean and confident like a good brushing. And nothing's more awkward than early morning kissing when you don't feel clean. If there's anything you squeeze into your purse, make it a toothbrush. But if you're uncomfortable letting your date know you're prepared, bring some travel toothpaste and keep it a secret.

Finding The Perfect Night-To-Day Outfit


If you're out on a weeknight, it's important to wear something that might appear professional in the morning, if you have to go straight to work. It can be very embarrassing to stumble down the street in wobbly heels at 6 a.m., so think about how that outfit would look in the early morning commute before you take it out on the town at night.

~Work Stuff~

Nothing's worth risking your professionalism and your reputation. When in doubt, bring your work things with you. If you have a late night and don't have time to go home in the morning before work, you'll be so mad at yourself that you weren't prepared.

Pre-Planning Your Footwear


Maybe heels look best with what you're wearing. But if you're going to be bold and take a risk, at least put a pair of ballet flats in your purse. They don't take up that much space and might save your life in the morning.

Forgetting Your Phone Charger

It's never presumptuous to carry around a phone charger. Lots of young professionals carry them around. Don't risk having a dead phone and being stranded or out of the loop or reach. Always bring your phone charger! Your life depends on it.

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