Situationship vs. Relationship: How to Turn Casual Dating Into Something Serious

Are you in a situationship? Are you unsure what the phrase even means? Is it the same as “friends with benefits”? Well, not quite… 

Just so we’re all clear here, let’s first define situationship. In essence, a situationship lies somewhere between a committed relationship and friendship. What makes a situationship unique is that neither party has a clear consensus on what it is. 

Unlike friends with benefits, where both people agree on what they’re doing (that being that they’re in a friendly relationship where there are occasional and casual sexual encounters), a situationship is a bit more nuanced. 

A situationship often arises after you’ve seen someone several times. While it’s clear both of you enjoy each other’s company and plan to continue spending time together, the problem is that an unspoken dynamic develops where neither of you takes the initiative to label the relationship. 

Why? Because—as we all know—relationships can get messy. Feelings can get hurt, jealousy can manifest, and before you know it, everything that made it fun to date the person in the first place has faded. 

Situationships are a solution to this problem because they are not committed relationships, and they take the pressure off both people to set clear parameters. 

Many men see situationship as an excellent opportunity for self-growth and personal freedom. For example, if you want to hang out with your buddies on Saturday night to watch the fight at a bar, you don’t have to run things by your significant other first. 

Similarly, should there come a time when you no longer want to spend time with this woman, you don’t even need to worry about breaking it off because there isn’t anything to break off. 

This is all fine, and if you are in a place where you’re not interested in a committed relationship—for example if you’re getting over a bad breakup or just aren’t ready for the commitment—situationship can be the ideal solution. 

The problem is you may start to develop feelings of wanting more. Now, this could be true for either person, but for the sake of this article, let’s assume you feel the need to transition from a situationship to a committed relationship. 

So, how do you do it? After all, you have a good thing going with this woman, and you don’t want to mess it up… But at the same time, you’re starting to develop deeper feelings, and this casual relationship is leaving you unsatisfied…

Well, as always, it’s a good idea to examine yourself… 

How Do I Know I Want to Turn a Situationship Into a Relationship?

First, before you start thinking about how to transition from a situationship to a relationship, make sure you’re clear on what you want. 

Take a minute and ask yourself, “What’s making me feel this way?” 

“Why do I want to get into a committed relationship with this person?” 

“What is it I’m hoping to gain?” 

Now, you might ask yourself these questions and find out that you have no honest answer. But then, at the same time, you have deep feelings for this person that aren’t being expressed in your current situation. In short: you’re completely confused. 

If that’s the case, take a breath and calm down. Let me tell you that it’s perfectly normal to feel this way. Furthermore, this may be uncharted territory for you, so it’s natural to feel a deep inner conflict.

Remember, seasoned men’s coaches have been in these situations before, so they can help you figure out what’s troubling you. Every man will have a unique situation, so having someone who will help you with your specific problems is always the best solution.

That said, here are a few things that might be why you’re feeling what you’re feeling. 

You genuinely enjoy her company.

It’s common for those in situationships to focus solely on superficial or sexual aspects of the relationship. But what if, as the two of you spend more time together, you find that your conversations actually draw you to her? 

If so, you may want to be around her more and more. But now, you have an internal conflict because, in the past, you never hung out more than once or twice a week. You don’t want to disrupt the status quo, but you also want to see her more, making you feel conflicted. 

You want stable support. 

If you’re in a situationship where the two of you hang out on weekends but rarely communicate during the week, you might also be left longing for more emotional support. 

Maybe you had a rough day at work and want someone to confide in. This is something that most people in healthy relationships can enjoy, but those in situationships may be lacking. 

You don’t like feeling confused. 

If you try to make plans in advance but get an evasive answer, you may quickly get frustrated. 

Let’s say you have a particular date for Saturday night, but she tells you she may or may not have plans with her girlfriends. Now, you—who has no plans—feel like you’re left in the dark, waiting for her reply. 

Of course, she isn’t doing anything wrong because this isn’t a relationship, but you still can’t help but feel like you wish things were somehow different.  

You’re beginning to feel jealous. 

Did she tell you that she won’t be able to hang out next weekend because her ex is going to be in town? Did she also tell you that the two of them are definitively broken and that this is nothing more than a platonic meeting? 

Did you hear all this and secretly feel jealous? Did you smile and say it was fine, but deep down, you felt like your relationship (correction, situationship) might be in jeopardy? Things like this could be a big sign that something needs to change for you.

Whatever the case, the key is that you must embrace the idea that this needs to change into a committed relationship. Once you know unequivocally what you want, here’s how to do it. 

1. Talk about it

This might be a shocker to some guys out there, but if you find yourself in a situationship and are yearning for something more, the easiest thing you can do is talk about it. 

For all you know, your partner might feel the same way that you do. Very often, two people who are dating will put up a front for the sake of keeping themselves from getting hurt. This nonchalant attitude is nothing more than a defense mechanism.

Of course, the opposite could also be true. Your partner might be completely content with how things are and have no interest or intention of changing. It’ll probably be an emotional blow to you if this is the case, but is it worse than not knowing?

Many men seem to struggle with bringing up the topic and then having it turn south. You like the woman you’ve been seeing and want to keep seeing her in the future, but you fear discussing things like this can ruin everything. 

Well, here’s the hard truth: it might ruin everything. 

But you’ll never know until you find out. So you have to ask yourself what your priorities are. If you’re content enough to allow things to continue as they are, you may, in fact, not be in a place where this needs to transition into a relationship. 

But if the current setup has become intolerable, you must muster up the strength and talk about it. You owe that to yourself. 

2. Define (at least some) of your boundaries

If you’re looking for a good place to start transitioning from a situationship to a relationship, setting some boundaries about who both of you are seeing is an excellent place to start. 

Note this doesn’t need to be a serious conversation where you clearly define every aspect of your relationship. Instead, frame it as a “Just so we both know…” conversation. Will both of you be allowed to see other people? Is this some open relationship? What’s the deal exactly? 

If you both agree that you’re not going to continue to see other people, that’s certainly a step in the right direction. And if she tells you that she would like to continue to see other people, don’t automatically assume that’s necessarily a bad thing, either. 

I know many men who married a specific woman after years of on-off dating. The truth is, sometimes, people need to explore their options before making a committed decision. 

You may feel like you’re at the point where you’re ready for a committed relationship, but there was probably a point in time when you weren’t. Dating and getting to know a person isn’t a black-and-white affair. No one is perfect—including her and including you—so, at the start, do your best to set clear boundaries and proceed from there. 

3. Show her different aspects of your life

Do you have something you’re passionate about that you’d think she’d enjoy? Are you a connoisseur of a certain type of food? Is there a band coming to town that you’ve loved since you were ten years old? Do you like taking an early morning run on Saturdays?

Why not invite her along? Show her the things that interest you. You might be surprised to learn that she secretly wants to do the same thing. 

If you find the two of you constantly repeating the same routine of going out to dinner, watching some television, and having sex, why not mix things up a little bit? If you want to show her you’re interested in her on more than just a superficial level, take some action to show her what you’re all about. 

If you feel like you can’t gauge whether or not she feels the same way as you, little activities like this can be a great way to get a better feel for the situation. 

4. Mix up your dating game

So you tried expressing your interests in sushi-topped pizza, found that the two of you have contrasting tastes in music and that your exercise routines are entirely incongruous. Now what? 

If attempting to do different activities fail, consider mixing up your dating routine a bit. If you usually grab a burger before heading back to your apartment, consider switching things up a bit by going to an upscale steakhouse. 

Tack on dinner or a play before or after the meal. See some live music at a dive bar. Do something silly, like playing mini-golf. Keep in mind you’re not doing anything drastically different than normal, but you’re providing space to talk and become more intimate. 

And whatever you do, don’t put too much pressure on the whole thing; you’re not pulling an engagement ring out of your pocket; you’re just trying to mix things up a bit. 

5. Introduce her to your friends

If you’re looking for another subtle way to show her you’re interested in turning your relationship into something more serious, mention that you’d like to introduce her to your friends and/or family. 

If you happen to be lucky enough to have a formal event coming up, inviting her to be a +1 is another great option. Alternatively, if you have that one friend who can’t do anything without his wife or girlfriend tagging along, this is the perfect excuse to turn it into a double date.  

Whatever you do, the key with this one is how you choose to phrase it. If you want to be very direct, then just flat-out saying that you like her and want her to meet your friends and family is the best option. 

At the same time, you can make it a bit more casual. For example, you might say that you and some of your friends are going camping or to a sporting event, and you’d love for her to come along. 

The two of you may have met each other through mutual friends, which might greatly diminish the impact of a gesture like this. Again, this is one of those instances where a men’s coach and support group can be a great asset. A coach can give you individualized support to reach your ultimate goals. 

6. Show her what your intentions are

It’s always wise to take a moment to try and consider things from the opposite point of view. Be mindful that your intentions might not be apparent to her, and she’s keeping her guard up because of that. 

After all, they call it “the dating game” for a reason. At the start of any relationship, whether a situationship or something more serious, there is always a period when both people have to feel each other out.

We tend to do that because most of us have had experiences in the past where we’ve been emotionally hurt. If you’re having difficulty reading her, consider that she might also have difficulty reading you. 

If you have every intention of having things progress to a more serious relationship, be sure to take actionable steps to make sure that’s clear to her. There are dozens of ways of doing this, but something as simple as a good morning text can go a long way in these situations. 

Also, minor goodwill gestures are always a safe bet. If she mentions needing help with something, you should help her if you can. If she says she has to return something to UPS and doesn’t have time to go, and if you also have something to ship, offer to take her package and help her out. 

Again, this is just an example, and don’t overthink it or put too much pressure on these things. The goal is to show her that you see her as more than a person you see once or twice a week for sex. If you want her to become a steady girlfriend, you must treat her like one. 

7. Let patience be your virtue

“Patience is the best remedy for every trouble.” –Plautus

When it comes to dating, there is no universal set of rules that apply to everyone, and this is especially true when we’re talking about the amount of time it takes for a relationship to progress. 

What do I mean by that? Well, I’ve met guys who met a woman and popped the question only three months later. I also know guys who have strict rules and won’t even consider marriage until a set amount of time has passed. One gentleman in particular actually has a three-year rule about this! 

Obviously, you’re probably not buying a ring anytime soon, but my point is, even though you might feel that it’s time to move things from situationship to relationship, it doesn’t mean she does. And it also doesn’t necessarily mean something is wrong. Sometimes, all you need to do is be patient. 

Everyone has different ideas and expectations of what a relationship should be, so don’t be too quick to jump to conclusions. It’s possible that she is just as interested in progressing things as you are, but she has different criteria for when that should happen. 

Coaches pride themselves on providing the knowledge that comes with experience to those who lack it. It’s that simple, and the coaching rules apply to all aspects of life, whether you’re talking about sports, business, dating, or life in general. 

8. When in doubt, consider giving an ultimatum

If you’ve tried everything on this list and still feel like you’re getting mixed signals, consider giving an ultimatum. People often say that men are the ones who are indecisive and can’t give their commitment to a relationship, but make no mistake, this can be just as true with women. 

If you’ve been going back and forth and are still struggling to get a clear answer on where you’re headed, you may have to be as direct as possible and give an ultimatum. Be as firm as possible, be clear on what you want, explain your expectations, and see if you can get a definitive answer. 

Most of all, be clear that you will leave if nothing changes. Depending on how long you’ve been in this situationship, a certain level of comfort may have developed on one or both sides. As is common in serious relationships, one or both of you may take the other for granted. 

This is entirely unhealthy, no matter how casual or serious a relationship is. You must do whatever is necessary to express yourself and make it abundantly clear that things will not continue as they are.  

9. Be prepared to explore the open waters

What is it that you really want? Do you want to develop a more serious relationship with this particular woman, or do you want a serious relationship with any woman?

If you’re unsure, you need to take a minute and seriously examine what you’re doing here. 

Lots of guys get hung up on one particular person and idealize them to the point that it becomes unhealthy. If you try to broach the topic of starting a serious relationship and it isn’t reciprocated, you may have no choice but to move on. 

Granted, there may be dozens of little nuances that are leaving you more confused than ever before. You also might find it difficult to cut off contact even though you know, objectively, that it is the right thing to do. 

This is where a support group and a seasoned men’s coach can prove invaluable. Yes, every situation is unique—as yours undoubtedly is—but so is everything else in life… 

Have you ever seen a sports coach who wasn’t somehow involved in the game for years before they sat behind the bench? Of course not. College players get drafted and go straight to the major leagues, but coaches most certainly do not. 

Experience is one of the deciding factors between success and failure. In decades past, men were left to figure things like this out the hard way. Thankfully, times have changed, and now there are coaches and teams of experts who can provide you with the real-world experience you need. 

My “band of brothers” are one such team, and if you’re ready to be a part of it, there’s never been a better time. Not only will you become part of a group of mature men, but you’ll also be free from all the complaining, naysaying, and negativity that dominate many men’s lives. 

Join us, and get access to the best training courses for men out there. Be part of our weekly calls and find yourself inspired by our determined coaches. Get the life you want. Get the relationship you want. 

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