September30 , 2022

16 Super Awkward Things That Happen In Every New Relationship

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Dating someone is supposed to be all rainbows and lollipops, right? Right?! Well, we hate to break it to ya, but it’s really not.

Ideally, new relationships would be one make out sesh followed by another make out sesh. Combine that with several witty, flirtatious conversations and text messages, starting a new relationship should be the best thing in the world. Only, there are times when new relationships aren’t rainbows and lollipops. In fact, new relationships can be awkward AF.

No matter how into the guy you are, you’re bound to experience a number of these awkward moments. Some of these are issues which arise when you’re becoming more intimate… like your first time together. Seriously, everything about your first time with someone is awkward. Movies starring Ryan Gosling and Channing Tatum make the first time seem like a hot, hot moment but the thing is, that isn’t usually the case. There’s also the issue of meeting those close to each other, like his parents. That is the most dreaded of all dreaded situations. Ah, but perhaps the worst of all of these situations is the first time he realizes you’re but a mere human being who doesn’t always wear makeup and farts. We all fart, people. Get over it.

Below are the 16 ~ MOST awkward ~ situations you’ll have to deal with when you’re in a new relationship. Enjoy the make out sessions, my friends, because the awkward moments are difficult to endure.

16The First Gift Exchange

If you start dating someone around the holiday season, bless your soul. The holidays are just a minefield of awkward relationship bombs waiting to detonate. Perhaps the worst of these relationship bombs is exchanging presents. Not only will you be challenged to buy him a gift that says, ‘Hey, I totally get you,’ but you’ll also have to deal with gauging how much you should be spending. You shouldn’t buy him a watch if he’s just buying you deodorant. Tiptoeing the line between ‘I totally get you’ and ‘I totally got you a present that is way too expensive’ is a hard task indeed.

The pressure will be off just a bit if you only have to buy him a gift without expecting one in return, like for his birthday. Though, there’s just the struggle of figuring out where the relationship stands and how much money you should be spending on him. Oh, there’s also the issue of what the hell to buy for guys.

15The “What Are We” Conversation

“What are we?” Everyone dreads this conversation and everything about it is awkward. In fact, we’d like to talk to whoever came up with the idea of labels and dating for this particular reason. It’s just such an awkward conversation to have.

The first issue is bringing the subject up. Whoever brings the subject up loses a bit of their power. We don’t like it either but that’s just the way it is. If you’re the one bringing it up, you’re usually the one who wants to be in an exclusive relationship.

The second huge issue is figuring out what page you’re both on. This conversation can suddenly reveal that one of you has thought the relationship was much more casual than the other. Oh, the horror. Unfortunately, the conversation is necessary if you want to be in an exclusive relationship with someone, but it’s just painful to actually talk through.

14The Protection Talk

Imagine this: a low-lit room, a heavy make out session, some sexy Kings of Leon playing in the background. It’s on a one-way trip to sex-ville and there is no stopping it. Well, there is one thing stopping it: the protection talk.

Way to ruin an intimate moment, but it’s an important talk that all new relationships must have. What kind of protection will you be using – a condom, birth control? Of course, being on birth control doesn’t guarantee protection from STDs and while the dude you’re hooking up with is probably ah-mazing, there’s no way to tell exactly what’s up with his downstairs area just from eyeing him up.

Having an awkward conversation about protection is the safest and most mature thing you can do before engaging in sex with someone for the first time. In fact, if you get this conversation out of the way before you’re in the dark room with Kings of Leon playing, more power to you. This way you won’t have to stop the train straight to sex-ville to talk about rubbers and STDs.

13The First Time You Do It

Alright, so after the protection talk there’s the actual sex. We’d love to think that it’s all hot and steamy. It’s the car scene from Titanic. It’s the rain scene from The Notebook. It’s every single Channing Tatum movie ever. But, uh, it’s not.

The thing about the first time with someone is that it’s usually really awkward. Sure, it will be special because you’re really into said person, but there’s also the maneuvering of each other’s bodies. You don’t know what he likes yet. He doesn’t know what you like yet. With the confusion, there is also the added pressure of the first time. You want to be so good, like the best sex ever. Between the confusion, pressure and insecurity, it’s usually a much more awkward time than a hot time.

We’re not saying your sex with him will never be hot. In fact, it’s bound to get hotter and hotter each time because you’ll no longer feel like strangers in the bedroom. The first time, though, there’s a learning curve… and it’s definitely an awkward learning curve.

12The First Time You Talk About Doing It

The best thing anyone can do for their sex life is be vocal about their wants and needs. If he isn’t fulfilling you, he won’t know unless you tell him… but that can be so very awkward. Sitting a guy down and telling him what he’s not doing right is one of the hardest conversations you can have, but it’s totally necessary if you really like him. You don’t want someone to stick around for forever if he can’t, y’know, take you all the way home. Broaching the subject must be done in a tactful manner because you don’t want to hurt his feelings.

Furthermore, even telling him that you liked some of the things he did can be awkward. In the heat of the moment, we’re okay with scratching, screaming and basically doing a ton of things that you wouldn’t normally do. After the deed is done, actually talking about what went down between the sheets can feel super weird, even if it’s a compliment.

11When You Wake Up With Him

Waking up with him can also be filed up there on the dreaded ‘him seeing you without makeup on’ tab.

Waking up tangled in each other’s limbs seems like an adorable concept but in reality, it’s not as adorable. To start with, there’s the morning breath factor. Unless you have time to sneak into the bathroom before he wakes up (a la Kristen Wiig in Bridesmaids) you’ll just have to deal with him knowing your morning breath. Oh, you’ll also totally have to deal with his, which can be seriously unattractive.

The other waking up together factor is the no makeup thing. Even if you’re a low maintenance girl, there’s a strong likelihood that you at least wear mascara around him. Waking up without your lashes lengthened or brows on fleek can be completely awkward. You may feel naked around him, even more so than when you’re actually naked. But, hey, you’re but a mere human and not a Victoria’s Secret model.

10Your First Farts

The horror of all horrors – farting around each other. We’re all human and farting, unfortunately, comes with the territory of being a human being. It’s something that happens and we just have to accept that. Accepting it, though, can be awkward AF.

Being a woman, it’s assumed that we don’t pass gas, which is an annoying stigma if we do say so. However, this stigma may make your guy a bit surprised if you pass a little gas in front of him. You may also be a bit embarrassed because, y’know, you just farted.

Women aren’t the only creatures that pass gas because guys totally do too. Having him fart in front of you can be an eye-opening experience. Instead of all the feels, you’ll have all the smells and dude farts can have a lot of smells. If the relationship is for the long hall, you should be able to fart in front of each other… but the first few times may just be really awkward.

9When You Have To Really Use The Bathroom

Peeing at his place is one thing. We can pee nearly everywhere. We’ll pee in a Starbucks bathroom. We’ll pee in a porter potty (if we really, really have to). Peeing is easy. It’s the other thing than can give us all the awkwardness in the world.

Nobody wants to do a number two at a guy’s place, especially if they are in a new relationship. I mean, what says ‘death of romance’ more? Unfortunately this, too, is part of being a human being. You may sometimes really have to use the bathroom and it might just happen to be at his place. You’ll just have to grin and bear it, but you can do things to make it less awkward. Bring some spray with you. Bring some matches with you. Run the faucet. Look at all the options you have!

No matter what, though, it will still feel awkward. Bodily functions can just be the worst when you’re in a new relationship.

8Meeting His Parents

What’s more awkward than meeting the people who gave birth to the guy you’re sleeping with? To them, he is their little, baby boy. To you, he’s, well… something else entirely. As a new relationship drifts into a more serious phase, this is something you will have to experience and it’s a pretty awkward experience.

When you do meet them, you’ll feel like you’re under a microscope. This is because you are. They are watching and judging everything you do. Even if they are sweet and welcoming, they are still judging you. Like we said, he is their baby boy. Their prized possession. The heir to the throne. You’re just some trollop who hooked up with their son. After the first few run ins with his parents, you’ll likely feel less judged and more like family. Until then, though, it can be excruciating.

7Meeting His Friends, Who You Already Know Way Too Much About

Meeting his friends can be less stressful than the meeting of his parents. That makes things a tad easier. However, meeting his friends can be awkward for a whole different reason. He’s most likely told you a ton of crazy information about his friends. You’ll know about all the zany hook ups they had. You’ll know that Tony fell asleep on the bathroom floor after a night of too much whiskey. You’ll know that Dave has an icky looking pinky toenail. You’ll have to walk the fine line of being friendly to his friends, but not spilling the beans on any of the information that you know, that you aren’t supposed to know.

To up the awkward factor, just think about all the information his friends know about you. Ugh, we know we aren’t helping but hey, you know about Dave’s pinky toenail and they all know about… well, they probably know a good deal about you to say the least. Sorry, girl. Kick back, drink some beers with them and hope the awkwardness fades.

6The Ex Conversation

You can avoid it all you want but it will surely come up. You know what we’re talking about: the dreaded ex conversation. Envisioning a guy you’re into being with anyone else in the world is painful. It can make you insane, but it is a necessary conversation.

In order to be in a relationship with someone, you kind of have to know his past. He may be just getting out of a long-term relationship and not want anything serious. Maybe, he’s never actually been in a relationship and doesn’t know what to do. Whatever the case, you’ll need to know his history and he’ll need to know yours. You may not want to fess up to your whole relationship history. It can be awkward if you’ve cheated on someone or hooked up with one of his friends in the past. Talking about the past is totally awkward but it’s sometimes necessary in order to have a future together.

5When You Realize You Didn’t Know Something Important

When you’re dating someone new, there’s always that strange moment when you realize that you didn’t know something that’s, well, important. It may be his birthday. Even the best Facebook stalking in the world may not reveal his birthday if he doesn’t have it on display. It could be that he has an allergy to peanuts, which you’ll find out when he tells you he can’t eat the peanut butter pie you ordered for dessert. Whatever the case, it will be a huge reminder that no matter how intimate you are, you still don’t know everything about each other.

There is shock value in that realization. No matter how much you think you know someone, you don’t know everything about them. This moment makes you wonder if you even know the person you’re dating at all. TBH, that may be the most awkward moment of all.

4Coming Out On Social Media

Coming out on social media is a big, big deal in a new relationship. To most people, the relationship isn’t really real unless it’s Facebook official. While it may sound odd, this has become a real gauge for relationships, and especially new relationships. It’s a milestone and it’s one that someone has to initiate. Even after you’ve had the ‘what are we’ conversation, being the person to put it out there on Facebook can make you feel awkward and goofy.

Before even the Facebook relationship thing though, there’s simply being linked on social media. We’re talking about statuses, checking in and photos together. Being the first one to make a move at all on social media can be awkward. If he hasn’t posted a photo of you two together, you might not know if you should. Are you out on social media or not? Ugh, the suspense during this point in your relationship can be painful.

3Your First Real Disagreement

This is a test that not all new relationships pass. The first real disagreement shows you just how strong or weak your relationship is. The thing about this first fight is that it’s actually really awkward.

Until your first disagreement, it is probably mostly rainbows, butterflies and sex. There’s the kissing, and the flirting, and the giddiness. It’s basically Candyland but real life. When the first fight happens, reality hits. It’s not going to just be fun forever. You’re going to have to discuss things and make decisions. What a snooze fest. It can also be awkward because who knew the two of you disagreed about things? Until this point, it probably seemed like you were on the same page about everything in life… and now, you’re not. Unfortunately, it’s just something you’re going to have to work through so you can moe on with your relationship.

2Your First Period

Guys know we get periods. We know we get periods. But, why is it so awkward to talk about periods?

If you’re sexually active, you’ll have to cross this bridge if he tries to have sex with you while Aunt Flow is in town. Side note: let’s all retire the Aunt Flow phrase. It’s totally outdated and just reminds us of Flo from the Progressive commercials.

If you’re on your period, he may be weirded out by it, as dudes are sometimes. The more awkward part can be the whole hanging out while you’re on your period. You may have to run to his bathroom to change your tampon and you may have leave the evidence behind. Ugh, why can’t the tampon goods just disappear into thin air? We don’t even want to leave the wrapper in their trashcans. If you’re staying over, there’s also the panic of possibly having an overnight issue. Just imagine staining his sheets. Yup, that’s the worst thing that could happen. Basically, having your period while you’re in a new relationship is a week full of anxiety and terror. New relationships are totally fun, right?

1When You Stop Doing It All The Time

This starts quietly but suddenly it hits you in the face: you are no longer having sex like bunnies. Some people think it happens only when you’ve been dating for a while, but the truth is that it can happen much earlier in the relationship. Most people cannot live without sleep and to have said sleep, you cannot have sex all through the night, every single night.

As the relationship keeps ticking on, you may find that you and your babe decide to binge-watch a show or actually sleep instead of having hours and hours of sex. This is awkward because it may seem alarming at first. Is he no longer interested in you? Has the chemistry disappeared? What is happening to your relationship? It’s all good, girl. It’s just that you’re a human being who cannot schedule hours of sex every single night. Talking about the fact that you are no longer having all the sex can be awkward because it’s a big, fat reminder that your relationship is sliding away from the hot beginning phase into the mild long-term phase. Sigh, we can’t all live in that hot, hot phase forever.

If you’re experiencing one of these super awkward relationship moments, you have our condolences. Just cherish the make out sessions. They will help you get through those awkward moments.